View source for Jake Gyllenhaal

{{short description|American actor (born 1980)}}
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{{Featured article}}
{{Use American English|date=January 2021}}
{{Use mdy dates|date=October 2025}}
{{Infobox person
| name               = Jake Gyllenhaal
| image              = Jake Gyllenhaal 2019 by Glenn Francis.jpg
| caption            = Gyllenhaal in 2019
| birth_name         = Jacob Benjamin Gyllenhaal
| birth_date         = {{Birth date and age|1980|12|19}}
| birth_place        = Los Angeles, California, U.S.
| alma_mater         = [[Columbia University]]
| occupation         = {{hlist|Actor|producer}}
| years_active       = 1991–present
| works              = [[Jake Gyllenhaal on screen and stage|Full list]]
| parents            = {{ubl|[[Stephen Gyllenhaal]]|[[Naomi Foner]]}}
| family             = [[Gyllenhaal family|Gyllenhaal]]
| awards             = [[List of awards and nominations received by Jake Gyllenhaal|Full list]]
| signature          = Jake Gyllenhaal's Signature.svg
}}

'''Jacob Benjamin Gyllenhaal''' ({{IPAc-en|ˈ|dʒ|ɪ|l|ə|n|h|ɔː|l}} {{respell|JIL|ən|hawl}},<ref>{{cite interview |last=Gyllenhaal |first=Jake |subject-link=Jake Gyllenhaal |interviewer-last=Pattanumotana |interviewer-first=Goon "Gig Patta" |title=An Actor Pronounces My Last Name Correctly |url=https://www.youtube.com/watch?v=Lur2tXyg-Iw |date=October 13, 2014 |access-date=April 26, 2020 |minutes=0:00 |archive-url=https://web.archive.org/web/20201101105128/https://www.youtube.com/watch?v=Lur2tXyg-Iw |archive-date=November 1, 2020 |url-status=live}}<br />'''Gig Patta:''' Good, good. And, um, just to wrap things up, I know you've been asked, you know, hundreds of times—I mean, how do you really pronounce your last name?<br />'''Gyllenhaal:''' How do you think you pronounce my last name?<br />'''Gig Patta:''' I thought it was pronounced /ˈdʒɪlənhɔːl/.<br />'''Gyllenhaal:''' You got it! That's it.<br />'''Gig Patta:''' Is that really...?<br />'''Gyllenhaal:''' Yeah, there's no need for me even to say it. You got it perfectly.</ref><ref>{{cite web |url=https://www.loc.gov/nls/about/organization/standards-guidelines/efgh/#g |title=NLS Other Writings Say How |access-date=October 1, 2017 |publisher=[[National Library Service for the Blind and Physically Handicapped]] |archive-url=https://web.archive.org/web/20181106205744/http://www.loc.gov/nls/about/organization/standards-guidelines/efgh/#g |archive-date=November 6, 2018 |url-status=live}}</ref> {{IPA|sv|ˈjʏ̂lːɛnˌhɑːl|lang}};<ref>{{cite interview |last=Gyllenhaal |first=Jake |subject-link=Jake Gyllenhaal |interviewer-last=O'Brien |interviewer-first=Conan |interviewer-link=Conan O'Brien |title=Nobody Says Jake Gyllenhaal's Name Correctly |url=https://teamcoco.com/video/highlight-nobody-says-jake-gyllenhaals-name-correctly |work=[[List of Conan episodes (2012)#September|Conan]]|publisher=[[TBS (American TV channel)|TBS]] |date=September 27, 2012  |access-date=January 16, 2020 |via=[[Team Coco]] |minutes=0:21 |quote=The only two places that it's pronounced correctly, my last name, like you did just now, is in Sweden and in IKEA. |archive-url=https://web.archive.org/web/20200116144919/https://teamcoco.com/video/highlight-nobody-says-jake-gyllenhaals-name-correctly |archive-date=January 16, 2020 |url-status=live}}</ref> born December 19, 1980) is an American actor whose [[Jake Gyllenhaal on screen and stage|career on screen and stage]] has spanned more than three decades. Born into the [[Gyllenhaal family]], he is the son of film director [[Stephen Gyllenhaal]] and screenwriter [[Naomi Foner]], and the younger brother of actress [[Maggie Gyllenhaal]].<ref>{{cite book |title=Sveriges Ridderskap och Adels kalender 2010 |page=302 |publisher=Riddarhuset |location=Stockholm |year=2009 |language=Swedish |isbn=978-91-633-5156-3 |issn=0347-9633}}</ref> 

Gyllenhaal began acting as a child, making his debut in ''[[City Slickers]]'' (1991), followed by roles in his father's films ''[[A Dangerous Woman (1993 film)|A Dangerous Woman]]'' (1993) and ''[[Homegrown (1998 film)|Homegrown]]'' (1998). His breakthrough roles were as [[Homer Hickam]] in the biopic ''[[October Sky]]'' (1999) and a troubled teenager in the thriller ''[[Donnie Darko]]'' (2001). Gyllenhaal expanded to big-budget films with a starring role in the 2004 disaster film ''[[The Day After Tomorrow]]''. Gyllenhaal played [[Jack Twist]] in [[Ang Lee]]'s 2005 romantic drama ''[[Brokeback Mountain]]'', for which he won a [[BAFTA Award]] and was nominated for an [[Academy Award]]. His career progressed with starring roles in the thriller ''[[Zodiac (film)|Zodiac]]'' (2007), the romantic comedy ''[[Love & Other Drugs]]'' (2010), and the science fiction film ''[[Source Code (film)|Source Code]]'' (2011). 

Further acclaim came with his roles in [[Denis Villeneuve]]'s thrillers ''[[Prisoners (2013 film)|Prisoners]]'' (2013) and ''[[Enemy (2013 film)|Enemy]]'' (2013). Gyllenhaal received nominations for the [[BAFTA Award for Best Actor in a Leading Role]] for his performances as a manipulative journalist in ''[[Nightcrawler (film)|Nightcrawler]]'' (2014) and a troubled writer in ''[[Nocturnal Animals]]'' (2016). His highest-grossing release came with the [[Marvel Cinematic Universe]] superhero film ''[[Spider-Man: Far From Home]]'' (2019), in which he portrayed [[Mysterio]]. After playing a supporting role in the drama ''[[Wildlife (film)|Wildlife]]'' (2018), Gyllenhaal starred in action or thriller projects, including the films ''[[The Guilty (2021 film)|The Guilty]]'' (2021), ''[[Ambulance (2022 film)|Ambulance]]'' (2022) and ''[[Road House (2024 film)|Road House]]'' (2024), as well as the series ''[[Presumed Innocent (TV series)|Presumed Innocent]]'' (2024).

Gyllenhaal has performed on stage, starring in a [[West End theatre|West End]] production of the play ''[[This Is Our Youth]]'' (2002) and [[Broadway theatre|Broadway]] productions of the musical ''[[Sunday in the Park with George]]'' (2017) as well as the plays ''[[Constellations (play)|Constellations]]'' (2014) and ''Sea Wall/A Life'' (2019), the last of which earned him a nomination for the [[Tony Award for Best Actor in a Play]]. Aside from acting, he is vocal about political and social issues.

==Life and career==
===1980–2000: Early life and career beginnings===
[[File:Gyllenhaal.jpg|thumb|upright|[[Coat of arms]] of the noble house [[Gyllenhaal family|Gyllenhaal]]|alt=Coat of arms of the noble house Gyllenhaal]]

Jacob Benjamin Gyllenhaal was born on December 19, 1980, in Los Angeles, California, United States, to screenwriter [[Naomi Foner]] ({{nee|Achs}}) and film director [[Stephen Gyllenhaal]].<ref>{{cite web |first=Dan |last=Rookwood |title=Jake Gyllenhaal On The Toughest Role Of His Career: 'Sometimes I Took It Too Far' |url=https://www.gq.com.au/entertainment/celebrity/jake+gyllenhaal+on+the+toughest+role+of+his+career,53285 |work=[[GQ Australia]] |date=January 11, 2018 |access-date=April 22, 2018 |archive-url=https://web.archive.org/web/20180421132446/http://www.gq.com.au/entertainment/celebrity/jake+gyllenhaal+on+the+toughest+role+of+his+career,53285 |archive-date=April 21, 2018 |url-status=live}}</ref><ref name="Schruers-2005" /> Actress [[Maggie Gyllenhaal]], his older sister, appeared with him in the science fiction psychological thriller film ''[[Donnie Darko]]'' (2001). Gyllenhaal's father, who was raised as a [[The New Church|Swedenborgian]], is a Christian<ref>{{Cite news |date=January 1, 2011 |title=Jake Gyllenhaal: My family values |url=https://www.theguardian.com/lifeandstyle/2011/jan/01/jake-gyllenhaal-my-family-values |access-date=December 21, 2024 |work=The Guardian |language=en-GB |issn=0261-3077 |archive-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730063733/https://www.theguardian.com/lifeandstyle/2011/jan/01/jake-gyllenhaal-my-family-values |url-status=live }}</ref> of Swedish and English descent and is a descendant of the Swedish noble [[Gyllenhaal family]].<ref>Stated on ''Finding Your Roots with Henry Louis Gates, Jr.'', PBS, April 22, 2012. Retrieved July 29, 2017.</ref> His last ancestor to be born in Sweden was his great-great-grandfather, Anders Leonard Gyllenhaal.<ref>{{cite web |url=http://www.gyllenhaal.org/AndersGyllenhaalObit.html |title=The Gyllenhaal Family Tree Project: Obituary of Anders Leonard Gyllenhaal |publisher=Gyllenhaal.org |date=July 9, 2000 |access-date=September 6, 2010 |archive-url=https://web.archive.org/web/20110727135755/http://www.gyllenhaal.org/AndersGyllenhaalObit.html |archive-date=July 27, 2011 |url-status=live}}</ref> Gyllenhaal's mother is Jewish,<ref>{{cite web |first=Susan |last=Josephs |title='Bee' Spells Family D-y-s-f-u-n-c-t-i-o-n-a-l |url=http://jewishjournal.com/culture/arts/12194/ |work=[[The Jewish Journal of Greater Los Angeles|Jewish Journal]] |date=November 10, 2005 |access-date=April 22, 2018 |archive-url=https://web.archive.org/web/20180624175909/http://jewishjournal.com/culture/arts/12194/ |archive-date=June 24, 2018 |url-status=live}}</ref><ref>{{cite web |first=Janet |last=Christie |title=Maggie Gyllenhaal: Acting for self-discovery |url=https://www.scotsman.com/lifestyle/culture/film/maggie-gyllenhaal-acting-for-self-discovery-1-3452677 |work=[[The Scotsman]] |date=June 22, 2014 |access-date=April 22, 2018 |archive-url=https://web.archive.org/web/20180422202128/https://www.scotsman.com/lifestyle/culture/film/maggie-gyllenhaal-acting-for-self-discovery-1-3452677 |archive-date=April 22, 2018 |url-status=live}}</ref><ref>{{cite web |first=Stephen |last=Applebaum |title=Jake Gyllenhaal: Going big – with a giant pig |url=https://www.thejc.com/culture/film/jake-gyllenhaal-okja-1.440374 |work=[[The Jewish Chronicle]] |date=June 22, 2017 |access-date=April 22, 2018 |archive-url=https://web.archive.org/web/20180422133003/https://www.thejc.com/culture/film/jake-gyllenhaal-okja-1.440374 |archive-date=April 22, 2018 |url-status=live}}</ref><ref>{{cite web |first=Gerard |last=Gilbert |url=https://www.independent.co.uk/arts-entertainment/tv/features/maggie-gyllenhaals-role-in-bbc2-spy-drama-the-honourable-woman-sounds-like-the-perfect-fit-even-with-9580264.html |title=Maggie Gyllenhaal on her new role in BBC2 spy drama The Honourable Woman |work=[[The Independent]] |date=July 2, 2014 |access-date=April 24, 2018 |archive-url=https://web.archive.org/web/20180424135927/https://www.independent.co.uk/arts-entertainment/tv/features/maggie-gyllenhaals-role-in-bbc2-spy-drama-the-honourable-woman-sounds-like-the-perfect-fit-even-with-9580264.html |archive-date=April 24, 2018 |url-status=live}}</ref> and was born in New York City into an [[Ashkenazi Jewish]] family from Russia and Poland.<ref>{{cite web |first=Naomi |last=Pfefferman |url=http://jewishjournal.com/current_edition/131226/ |title=Maggie Gyllenhaal stars in SundanceTV's "The Honorable Woman" |work=[[The Jewish Journal of Greater Los Angeles|Jewish Journal]] |date=July 23, 2014 |access-date=April 24, 2018 |archive-url=https://web.archive.org/web/20180424135239/http://jewishjournal.com/current_edition/131226/ |archive-date=April 24, 2018 |url-status=live}}</ref><ref>{{Cite news |first=Tim |last=Adams |title=Jake Gyllenhaal: 'Pushing myself is part of my life' |url=https://www.theguardian.com/film/2016/apr/24/jake-gyllenhaal-interview-pushing-myself-is-part-of-my-life-film-demolition |work=[[The Guardian]] |date=April 24, 2016 |access-date=April 22, 2018 |archive-url=https://web.archive.org/web/20180422201948/https://www.theguardian.com/film/2016/apr/24/jake-gyllenhaal-interview-pushing-myself-is-part-of-my-life-film-demolition |archive-date=April 22, 2018 |url-status=live}}</ref> Gyllenhaal has said that he considers himself Jewish.<ref>{{cite web |url=https://www.jewishtampa.com/jews-in-the-news/jews-in-the-newssarah-michelle-gellar-julianne-margulies-and-jake-gyllenhaal |title=Jews in the News:Sarah Michelle Gellar, Julianne Margulies and Jake Gyllenhaal |date=October 3, 2013 |work=jewishtampa.com |publisher=Tampa Jewish Community Center & Federation |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730015158/https://www.jewishtampa.com/jews-in-the-news/jews-in-the-newssarah-michelle-gellar-julianne-margulies-and-jake-gyllenhaal |archive-date=July 30, 2017 |url-status=live}}</ref><ref>{{cite web |url=http://www.ugo.com/movies/jake-gyllenhall-interview.html |title=Jake Gyllenhaal Interview – ''Prince of Persia'' |work=ugo.com |access-date=July 18, 2015 |archive-url=https://web.archive.org/web/20150721190105/http://www.ugo.com/movies/jake-gyllenhall-interview.html |archive-date=July 21, 2015 |url-status=live}}</ref> Gyllenhaal is [[legally blind]] and has been wearing corrective lenses since he was 6.<ref>{{cite web |publisher=[[The Hollywood Reporter]] |date=June 5, 2024 |url=https://www.hollywoodreporter.com/movies/movie-features/jake-gyllenhaal-interview-presumed-innocent-road-house-othello-1235914641/ |title=Jake Gyllenhaal Just Wants to Freak Himself Out |access-date=May 31, 2025}}</ref> On his 13th birthday, Gyllenhaal performed a "[[Bar Mitzvah]]-like act, without the typical trappings", volunteering at a [[homeless shelter]] because his parents wanted to give him a sense of gratitude for his privileged lifestyle.<ref>{{cite web |publisher=Contact Music |date=November 6, 2005 |url=http://www.contactmusic.com/new/xmlfeed.nsf/mndwebpages/gyllenhaals%20homeless%20shelter%20bar-mitzvah |title=Gyllenhaal's Homeless Shelter Bar-Mitzvah |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20090112205803/http://www.contactmusic.com/new/xmlfeed.nsf/mndwebpages/gyllenhaals%20homeless%20shelter%20bar-mitzvah |archive-date=January 12, 2009 |url-status=live}}</ref><ref>{{cite news |last=Lipworth |first=Elaine |title=Jake Gyllenhaal: My family values |work=[[The Guardian]] |location=UK |date=January 1, 2011 |url=https://www.theguardian.com/lifeandstyle/2011/jan/01/jake-gyllenhaal-my-family-values |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730063733/https://www.theguardian.com/lifeandstyle/2011/jan/01/jake-gyllenhaal-my-family-values |archive-date=July 30, 2017 |url-status=live}}</ref>

As a child, Gyllenhaal was regularly exposed to filmmaking due to his family's ties to the industry. He made his acting debut as [[Billy Crystal]]'s son in the 1991 comedy ''[[City Slickers]]''. His parents did not allow him to appear in ''[[The Mighty Ducks (film)|The Mighty Ducks]]'' (1992) because it would have required him to leave home for two months.<ref name="Schruers-2005">{{cite news |last=Schruers |first=Fred |date=October 30, 2005 |url=https://www.theguardian.com/film/2005/oct/30/awardsandprizes.oscars2006 |title=Jake's progress |work=The Guardian |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730020212/https://www.theguardian.com/film/2005/oct/30/awardsandprizes.oscars2006 |archive-date=July 30, 2017 |url-status=live}}</ref> In subsequent years, his parents allowed him to audition for roles but regularly forbade him to take them if he were chosen.<ref name="Horn">{{Cite web |last=Horn |first=Steven |date=May 28, 2004 |title=Interview with Jake Gyllenhaal |url=https://www.ign.com/articles/2004/05/28/interview-with-jake-gyllenhaal |access-date=February 29, 2020 |website=[[IGN]] |language=en |archive-date=January 11, 2012 |archive-url=https://web.archive.org/web/20120111174546/https://movies.ign.com/articles/519/519613p1.html |url-status=live }}</ref> He was allowed to appear in his father's films several times. Gyllenhaal appeared in the 1993's ''[[A Dangerous Woman (1993 film)|A Dangerous Woman]]'' (along with sister Maggie), in "[[Bop Gun (Homicide: Life on the Street)|Bop Gun]]", a 1994 episode of ''[[Homicide: Life on the Street]]''; and in the 1998 comedy ''[[Homegrown (1998 film)|Homegrown]]''. Along with their mother, Jake and Maggie appeared in two episodes of ''Molto Mario'', an Italian cooking show on the [[Food Network]]. Prior to his senior year in high school, the only other film not directed by his father in which Gyllenhaal was allowed to perform was the 1993 film ''[[Josh and S.A.M.]]'', a little-known children's adventure.<ref name="Wills">{{Cite web |last=Willis |first=Dominic |date=2006 |title=Jake Gyllenhaal - Biography |url=http://www.talktalk.co.uk/entertainment/film/biography/artist/jake-gyllenhaal/biography/161 |url-status=dead |archive-url=https://web.archive.org/web/20151019154058/http://www.talktalk.co.uk/entertainment/film/biography/artist/jake-gyllenhaal/biography/161 |archive-date=October 19, 2015 |access-date=March 15, 2025 |website=TalkTalk}}</ref>

His parents insisted that he have summer jobs to support himself, and he thus worked as a lifeguard and as a [[busboy]] at a restaurant operated by a family friend.<ref name="Horn" /> Gyllenhaal said his parents encouraged artistic expression: "I do have parents who constantly supported me in certain ways. In other ways, they were lacking. Definitely, it's in expression and creativity where my family has always been best at."<ref>{{cite news |last=Nepales |first=Ruben V. |title=Jake Gyllenhaal shares views on sensitivity and masculinity |url=https://entertainment.inquirer.net/206425/jake-gyllenhaal-shares-views-on-sensitivity-and-masculinity |newspaper=[[Philippine Daily Inquirer]] |date=December 14, 2016 |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730065006/http://entertainment.inquirer.net/206425/jake-gyllenhaal-shares-views-on-sensitivity-and-masculinity |archive-date=July 30, 2017 |url-status=live}}</ref> Gyllenhaal graduated from the [[Harvard-Westlake School]], a private school in Los Angeles in 1998, then attended [[Columbia University]], where his sister was a senior and from which his mother had graduated, to study [[Eastern religions]] and philosophy. At Columbia, he was a resident of [[John Jay Hall]].<ref>{{Cite web |title=Columbia Spectator 25 March 2005 — Columbia Spectator |url=https://spectatorarchive.library.columbia.edu/?a=d&d=cs20050325-03.2.17&srpos=11&e=-------en-20--1--txt-txIN-%22Jake+Gyllenhaal%22------ |access-date=November 14, 2021 |website=spectatorarchive.library.columbia.edu |archive-date=July 18, 2022 |archive-url=https://web.archive.org/web/20220718025228/https://spectatorarchive.library.columbia.edu/?a=d&d=cs20050325-03.2.17&srpos=11&e=-------en-20--1--txt-txIN-%22Jake+Gyllenhaal%22------ |url-status=live}}</ref> Gyllenhaal dropped out after two years to concentrate on acting but has expressed intentions to eventually finish his degree.<ref name="Schruers-2005" /> Gyllenhaal's first lead role was in ''[[October Sky]]'', [[Joe Johnston]]'s 1999 adaptation of the [[Homer Hickam]] autobiography ''[[Rocket Boys]]'', in which he portrayed a young man from [[West Virginia]] striving to win a science scholarship to avoid becoming a coal miner. The film was positively received and earned $32&nbsp;million; it was described in the ''[[Sacramento News and Review]]'' as Gyllenhaal's "breakout performance".<ref name="Wills" /><ref>{{cite web |last=Halverson |first=Mark |year=1998 |url=https://www.rottentomatoes.com/m/october_sky/articles/167357/a_breakout_performance_by_jake_gyllenhaal |title=A breakout performance by Jake Gyllenhaal! |work=Rotten Tomatoes |access-date=September 21, 2006 |archive-url=https://web.archive.org/web/20080626103608/http://www.rottentomatoes.com/m/october_sky/articles/167357/a_breakout_performance_by_jake_gyllenhaal |archive-date=June 26, 2008 |url-status=dead}}</ref>

===2001–2004: ''Donnie Darko'' to the London stage===
''Donnie Darko'', in which Gyllenhaal played his second lead role on film, was not a box office success on its initial 2001 release; eventually, the film became a [[Cult film|cult favorite]].<ref>{{cite news |last=Snider |first=Mike |date=February 2, 2005 |url=https://www.usatoday.com/life/movies/news/2005-02-14-dvd-donnie-darko_x.htm |title='Darko' takes a long, strange trip |work=[[USA Today]] |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20110212091838/http://www.usatoday.com/life/movies/news/2005-02-14-dvd-donnie-darko_x.htm |archive-date=February 12, 2011 |url-status=live}}</ref> Directed by [[Richard Kelly (director)|Richard Kelly]], the film is set in 1988 and stars Gyllenhaal as a troubled teenager who experiences visions of a {{convert|6|ft|m|abbr=off|spell=in|adj=mid|-tall|sp=us}} rabbit named Frank who tells him that the world is coming to an end. Gyllenhaal's performance was well received by critics; Gary Mairs of ''Culture Vulture'' wrote that he "manages the difficult trick of seeming both blandly normal and profoundly disturbed, often within the same scene."<ref>{{cite web |last=Kois |first=Dan |date=July 23, 2004 |url=http://www.salon.com/2004/07/23/darko/ |title=Everything you were afraid to ask about 'Donnie Darko' |website=Salon |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20111027192436/http://www.salon.com/2004/07/23/darko |archive-date=October 27, 2011 |url-status=live}},''Salon.com''</ref><ref>{{cite web |last=Mairs |first=Gary |url=http://www.culturevulture.net/Movies3/DonnyDarko.htm |title=Donnie Darko review |website=CultureVulture.net |access-date=September 21, 2006 |archive-url=https://web.archive.org/web/20060615103304/http://culturevulture.net/Movies3/DonnyDarko.htm |archive-date=June 15, 2006 |url-status=dead}}</ref>

Gyllenhaal's next role was as Pilot Kelston in 2002's ''[[Highway (2002 film)|Highway]]'' alongside [[Jared Leto]]. His performance was described by one critic as "silly, clichéd and [[Direct-to-video|straight to video]]".<ref name="Wills" /> Gyllenhaal had more success starring opposite [[Jennifer Aniston]] in ''[[The Good Girl]]'', which premiered at the 2002 [[Sundance Film Festival]]; he also starred in ''[[Lovely and Amazing]]'' with [[Catherine Keener]].<ref>{{cite news |last=Hubbell |first=Anne |date=January 16, 2002 |url=http://edition.cnn.com/2002/SHOWBIZ/Movies/01/16/sun.white/index.html |title=Director, writer talk about 'The Good Girl' |publisher=CNN Entertainment |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730080748/http://edition.cnn.com/2002/SHOWBIZ/Movies/01/16/sun.white/index.html |archive-date=July 30, 2017 |url-status=live}}</ref> In both films he plays an unstable character who begins a reckless affair with an older woman. Gyllenhaal later described these as "teenager in transition" roles.<ref>{{cite web |last=Michael |first=David |date=October 21, 2002 |url=https://www.bbc.co.uk/films/2002/10/21/jake_gyllenhaal_donnie_darko_interview.shtml |title=BBC Films |access-date=September 19, 2006 |archive-url=https://web.archive.org/web/20060710012806/http://www.bbc.co.uk/films/2002/10/21/jake_gyllenhaal_donnie_darko_interview.shtml |archive-date=July 10, 2006 |url-status=live}}</ref> Gyllenhaal later starred in the [[Touchstone Pictures]] romantic comedy ''[[Bubble Boy (film)|Bubble Boy]]'', which was loosely based on the story of [[David Vetter]]. The film portrays the title character's adventures as he pursues the love of his life before she marries the wrong man.<ref>{{cite web |last=Gonzalez |first=Ed |year=2001 |url=https://www.slantmagazine.com/film/film_review.asp?ID=71 |title=''Slant Magazine'' review |website=[[Slant Magazine]] |access-date=September 19, 2006 |archive-url=https://web.archive.org/web/20060505080420/http://www.slantmagazine.com/film/film_review.asp?ID=71 |archive-date=May 5, 2006 |url-status=dead}}</ref> The film was panned by critics,<ref>{{Citation |title=Bubble Boy (2001) |url=https://www.rottentomatoes.com/m/bubble_boy |work=[[Rotten Tomatoes]] |date=August 24, 2001 |access-date=April 7, 2021 |archive-date=April 30, 2019 |archive-url=https://web.archive.org/web/20190430124500/https://www.rottentomatoes.com/m/bubble_boy |url-status=live}}</ref> with one calling it "stupid and devoid of any redeeming features".<ref>{{Cite web |last=Clinton |first=Paul |date=August 24, 2001 |title=CNN.com - 'Bubble Boy' bursting with dumb humor - August 24, 2001 |url=http://edition.cnn.com/2001/SHOWBIZ/Movies/08/24/review.bubble.boy/index.html |url-status=live |access-date=April 7, 2021 |publisher=CNN |archive-date=October 4, 2020 |archive-url=https://web.archive.org/web/20201004092753/http://edition.cnn.com/2001/SHOWBIZ/Movies/08/24/review.bubble.boy/index.html}}</ref>

Following ''Bubble Boy'', Gyllenhaal starred opposite [[Dustin Hoffman]], [[Susan Sarandon]] and [[Ellen Pompeo]] in ''[[Moonlight Mile (film)|Moonlight Mile]]'' (2002), as a young man coping with the death of his fiancée and the grief of her parents. The story, which received mixed reviews,<ref>{{cite web |url=https://www.rottentomatoes.com/m/moonlight_mile/ |title=RottenTomatoes.com compilation of critical reviews |website=[[Rotten Tomatoes]] |date=October 4, 2002 |access-date=July 29, 2017 |archive-url=https://web.archive.org/web/20170422112643/https://www.rottentomatoes.com/m/moonlight_mile/ |archive-date=April 22, 2017 |url-status=live}}</ref> is loosely based on writer-director [[Brad Silberling]]'s personal experiences following the murder of his girlfriend, [[Rebecca Schaeffer]].<ref>{{Cite web |last=Ojumu |first=Akin |date=February 16, 2003 |title=Brad Silberling: The family that grieves together... |url=http://www.theguardian.com/film/2003/feb/16/features.review |url-status=live |access-date=April 7, 2021 |website=[[The Guardian]] |archive-date=March 8, 2021 |archive-url=https://web.archive.org/web/20210308205122/https://www.theguardian.com/film/2003/feb/16/features.review}}</ref> In his theatrical debut, Gyllenhaal starred on the London stage in [[Kenneth Lonergan]]'s revival of ''[[This Is Our Youth]]'' at the [[Garrick Theatre]] in 2002.<ref>{{cite news |author=Billington, Michael |date=March 18, 2002 |url=https://www.theguardian.com/stage/2002/mar/18/theatre.artsfeatures |title=''This Is Our Youth'' review |work=[[The Guardian]] |access-date=July 30, 2017 |author-link=Michael Billington (critic) |archive-url=https://web.archive.org/web/20200216103512/https://www.theguardian.com/stage/2002/mar/18/theatre.artsfeatures |archive-date=February 16, 2020 |url-status=live}}</ref> Gyllenhaal said, "Every actor I look up to has done theatre work, so I knew I had to give it a try."<ref>{{cite news |last1=Gritten |first1=David |date=April 13, 2002 |url=https://www.telegraph.co.uk/arts/main.jhtml?xml=/arts/2002/04/13/btgrit13.xml |title=Fast growing up to be famous |work=[[The Daily Telegraph]] |access-date=September 19, 2006 |archive-url=https://web.archive.org/web/20071012130612/http://www.telegraph.co.uk/arts/main.jhtml?xml=%2Farts%2F2002%2F04%2F13%2Fbtgrit13.xml |archive-date=October 12, 2007 |url-status=dead}}</ref> The play ran for eight weeks in London's [[West End theatre|West End]]; Gyllenhaal received favorable reviews and an [[Evening Standard Theatre Award]] in the Outstanding Newcomer category.<ref>{{Cite web |title=This is Our Youth in London |url=http://www.thisistheatre.com/londonshows/thisisouryouth.html |access-date=April 7, 2021 |website=This Is Theatre |archive-date=June 13, 2021 |archive-url=https://web.archive.org/web/20210613135609/http://www.thisistheatre.com/londonshows/thisisouryouth.html |url-status=live}}</ref><ref>{{cite web |publisher=Albemarle-London |url=http://www.albemarle-london.com/awards/AwardWinners.php?Award_Type=Evening+Standard+Awards&Year=2002 |title=Albemarle |access-date=October 8, 2009 |archive-url=https://web.archive.org/web/20061023103112/http://www.albemarle-london.com/awards/AwardWinners.php?Award_Type=Evening%20Standard%20Awards&Year=2002 |archive-date=October 23, 2006 |url-status=dead}}</ref>

Gyllenhaal was almost cast as [[Spider-Man]] for 2004's ''[[Spider-Man 2]]'', due to director [[Sam Raimi]]'s concerns about original ''[[Spider-Man (2002 film)|Spider-Man]]'' star [[Tobey Maguire]]'s health.<ref>{{cite web |last=Otto |first=Jeff |url=https://www.ign.com/articles/2003/07/23/an-interview-with-tobey-maguire |title=An Interview with Tobey Maguire |website=IGN |date=July 23, 2003 |access-date=February 29, 2020 |archive-url=https://web.archive.org/web/20190525172359/https://www.ign.com/articles/2003/07/23/an-interview-with-tobey-maguire |archive-date=May 25, 2019 |url-status=live}}</ref> Maguire recovered, however, and the sequel was shot without Gyllenhaal.<ref>{{cite web |last=Morales |first=Wilson |date=June 2004 |url=http://www.blackfilm.com/20040625/features/samraimi.shtml |title=Spiderman 2: An Interview with Sam Raimi |website=Blackfilm.com |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170219190120/http://www.blackfilm.com/20040625/features/samraimi.shtml |archive-date=February 19, 2017 |url-status=live}}</ref> The actors later starred together in ''Brothers'' (2009), and resemble each other enough that Gyllenhaal has jokingly complained about cab drivers often calling him "Spider-Man".<ref>{{cite news |url=https://www.telegraph.co.uk/culture/film/6947353/Jake-Gyllenhaal-interview.html |title=Jake Gyllenhaal interview |work=The Daily Telegraph |date=January 7, 2010 |access-date=July 30, 2017 |last=Lawrence |first=Will |location=London |archive-url=https://web.archive.org/web/20170805071843/http://www.telegraph.co.uk/culture/film/6947353/Jake-Gyllenhaal-interview.html |archive-date=August 5, 2017 |url-status=live}}</ref> In 2003, he also auditioned for the role of Batman in the superhero film ''[[Batman Begins]]'' and came close being offered the part, but it was given to [[Christian Bale]].<ref>{{cite web |first=Stephen M. |last=Silverman |url=http://people.com/celebrity/jake-gyllenhaal-the-new-batman/ |title=Jake Gyllenhaal: The New Batman? |work=[[People (magazine)|People]] |date=September 3, 2003 |access-date=July 30, 2017 |author-link=Stephen M. Silverman |archive-url=https://web.archive.org/web/20170730023456/http://people.com/celebrity/jake-gyllenhaal-the-new-batman/ |archive-date=July 30, 2017 |url-status=live}}</ref><ref>{{cite web |last=Otto |first=Jeff |url=https://www.ign.com/articles/2004/02/27/david-s-goyer-talks-batman-iron-man-comics-and-more |title=David S. Goyer Talks Batman, Iron Man, Comics and More |website=[[IGN]] |date=February 27, 2004 |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170731003245/http://www.ign.com/articles/2004/02/27/david-s-goyer-talks-batman-iron-man-comics-and-more |archive-date=July 31, 2017 |url-status=live}}</ref> Gyllenhaal subsequently appeared in the science fiction [[Blockbuster (entertainment)|blockbuster]] ''[[The Day After Tomorrow]]'' in 2004, co-starring [[Dennis Quaid]] as his father.<ref name="Schruers-2005" /><ref>{{cite web |last=Mottram |first=James |date=May 12, 2004 |url=https://www.bbc.co.uk/films/2004/05/12/jake_gyllenhaal_day_after_tomorrow_interview.shtml |title=BBC Film |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170219190109/http://www.bbc.co.uk/films/2004/05/12/jake_gyllenhaal_day_after_tomorrow_interview.shtml |archive-date=February 19, 2017 |url-status=live}}</ref>

===2005–2011: ''Brokeback Mountain'' and leading roles===
[[File:Proof 004 (7288885150).jpg|thumb|upright|Gyllenhaal attending the premiere of ''[[Proof (2005 film)|Proof]]'' at the [[2005 Toronto International Film Festival]]|alt=Gyllenhaal attending the premiere of Proof, 2005]]

In 2005, Gyllenhaal was cast in the drama ''[[Proof (2005 film)|Proof]]'', with co-stars [[Gwyneth Paltrow]] and [[Anthony Hopkins]], where he played a graduate student in mathematics who tries to convince Paltrow's character to publish a revolutionary [[mathematical proof|proof]] to a problem puzzling the mathematicians' community. The film received a generally positive response. He also starred in [[Sam Mendes]]'s ''[[Jarhead (film)|Jarhead]]'', where Gyllenhaal played a [[United States Marine Corps|U.S. Marine]] during the first [[Gulf War]]. The film garnered a favorable response; [[Stephen Hunter]] of ''[[The Washington Post]]'' praises Gyllenhaal's performance, writing, "He makes us see his character's intelligence", adding "he doesn't seem jealous of the camera's attention when it goes to others".<ref>{{Cite news |last=Hunter |first=Stephen |date=November 4, 2005 |title='Jarhead': A Platoon Full of Sand And Grit |newspaper=[[The Washington Post]] |url=http://www.washingtonpost.com/wp-dyn/content/article/2005/11/03/AR2005110302427.html |access-date=May 18, 2020 |issn=0190-8286 |archive-url=https://web.archive.org/web/20190905135704/http://www.washingtonpost.com/wp-dyn/content/article/2005/11/03/AR2005110302427.html |archive-date=September 5, 2019 |url-status=live}}</ref>

In ''[[Brokeback Mountain]]'' (2005), Gyllenhaal and [[Heath Ledger]] play young men who meet as sheep herders and embark upon a sexual relationship that begins in the summer of 1963 and lasts for 20 years.<ref name="Hiscock-2005">{{cite news |last=Hiscock |first=John |date=December 12, 2005 |url=https://www.telegraph.co.uk/arts/main.jhtml?xml=/arts/2005/12/10/bfgyllen10.xml |title=The one Jake: why Gyllenhaal spells success |work=The Telegraph |access-date=November 6, 2006 |archive-url=https://web.archive.org/web/20060405163151/http://www.telegraph.co.uk/arts/main.jhtml?xml=%2Farts%2F2005%2F12%2F10%2Fbfgyllen10.xml |archive-date=April 5, 2006 |url-status=dead}}</ref> The film was often referred to in the media with the shorthand phrase "the gay cowboy movie",<ref>{{cite web |url=http://www.indyweek.com/gyrobase/Content?oid=oid%3A27050 |first=Godfrey |last=Cheshire |work=[[The Independent Weekly]] |title=Somewhere over the rainbow |date=January 4, 2006 |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20160110164519/http://www.indyweek.com/gyrobase/Content?oid=oid%3A27050 |archive-date=January 10, 2016 |url-status=dead}}</ref> although there was [[Brokeback Mountain#Characters' sexuality|differing opinion]] on the sexual orientation of the characters. The film won numerous accolades, including the [[Golden Lion]] prize at the [[Venice Film Festival]].<ref>{{Cite news |date=September 11, 2005 |title=Ang Lee wins Golden Lion at Venice Film Festival |work=[[The New York Times]] |url=https://www.nytimes.com/2005/09/11/world/europe/ang-lee-wins-golden-lion-at-venice-film-festival.html |access-date=May 18, 2020 |issn=0362-4331 |archive-date=November 1, 2020 |archive-url=https://web.archive.org/web/20201101105129/https://www.nytimes.com/2005/09/11/world/europe/ang-lee-wins-golden-lion-at-venice-film-festival.html |url-status=live}}</ref> The film won three Academy Awards, and earned Gyllenhaal a nomination for [[Academy Award for Best Supporting Actor|Best Supporting Actor]], but he lost to [[George Clooney]] for ''[[Syriana]]''.<ref>{{Cite web |title=The 78th Academy Awards {{!}} 2006 |url=https://www.oscars.org/oscars/ceremonies/2006 |publisher=[[Academy of Motion Picture Arts and Sciences]] |access-date=May 18, 2020 |archive-url=https://web.archive.org/web/20151102070203/https://www.oscars.org/oscars/ceremonies/2006 |archive-date=November 2, 2015 |url-status=live}}</ref> The film also won four Golden Globes, and four [[British Academy of Film and Television Arts|British Academy Film Awards]] (BAFTAs), in which Gyllenhaal won for [[British Academy Television Award for Best Supporting Actor|Best Supporting Actor]].<ref>{{Cite web |title=Film in 2006 {{!}} BAFTA Awards |url=http://awards.bafta.org/award/2006/film |publisher=[[British Academy of Film and Television Arts]] |access-date=May 18, 2020 |archive-url=https://web.archive.org/web/20160305144619/http://awards.bafta.org/award/2006/film |archive-date=March 5, 2016 |url-status=live}}</ref> He and Ledger won an [[MTV Movie Award for Best Kiss]] in 2006. Shortly after the [[78th Academy Awards|2006 Academy Awards]], Gyllenhaal was invited to join the Academy in recognition of his acting career.<ref>{{cite press release |date=July 6, 2006 |url=http://www.oscars.org/press/pressreleases/2006/06.07.01a.html |title=Academy Invites 120 to Membership |publisher=[[Academy of Motion Picture Arts and Sciences]] |access-date=September 7, 2008 |archive-url=https://web.archive.org/web/20060706181947/http://www.oscars.org/press/pressreleases/2006/06.07.01a.html |archive-date=July 6, 2006 |url-status=dead}}</ref>

Gyllenhaal expressed mixed feelings about the experience of being directed by [[Ang Lee]] in ''Brokeback Mountain'' but generally had more praise than criticism for his directorial style. While critical of the way Lee tended to disconnect from his actors once filming began, Gyllenhaal praised his encouraging direction of the actors and sensitive approach to the material.<ref>{{cite news |author=Wenn |date=December 20, 2005 |url=http://www.hollywood.com/news/Gyllenhaal_Suffered_with_Unfriendly_Lee_/3472467 |title=Jake Gyllenhaal Suffered with Unfriendly Ang Lee |website=Hollywood.com |access-date=July 30, 2017 |archive-url=https://archive.today/20120525083040/http://www.hollywood.com/news/Gyllenhaal_Suffered_with_Unfriendly_Lee_/3472467 |archive-date=May 25, 2012 |url-status=live}}</ref><ref>{{Cite web |last=Cavagna |first=Carlo |date=December 2005 |title=Interview: Jake Gyllenhaal |url=https://www.aboutfilm.com/movies/b/brokebackmountain/gyllenhaal.htm |access-date=September 19, 2006 |website=aboutfilm.com}}</ref> At the [[Directors Guild of America Award]]s on January 28, 2006, Gyllenhaal also praised Lee for "his humbleness and his respect for everyone around him".<ref>{{cite news |publisher=[[CBS News]] |date=January 26, 2005 |url=https://www.cbsnews.com/news/brokeback-director-grabs-top-award/ |title='Brokeback' Director Grabs Top Award |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730021947/http://www.cbsnews.com/news/brokeback-director-grabs-top-award/ |archive-date=July 30, 2017 |url-status=live}}</ref> When asked about his kissing scenes with Ledger in ''Brokeback Mountain'', Gyllenhaal said, "As an actor, I think we need to embrace the times we feel most uncomfortable."<ref>{{cite web |last1=Denizet-Lewis |first1=Benoit |url=http://men.style.com/details/features/full?id=content_4026&pageNum=2 |title=Jake |website=[[Style.com]] |access-date=September 19, 2006 |archive-url=https://web.archive.org/web/20070930204150/http://men.style.com/details/features/full?id=content_4026&pageNum=2 |archive-date=September 30, 2007 |url-status=dead}}</ref> When asked about the more intimate scenes with Ledger, Gyllenhaal likened them to "doing a [[sex scene]] with a woman I'm not particularly attracted to".<ref name="Hiscock-2005" /> Following the release of ''Brokeback Mountain'', rumors circulated regarding the actor's [[sexual orientation]]. When asked about such gossip during an interview, Gyllenhaal said: {{blockquote|You know it's flattering when there's a rumor that says I'm bisexual. It means I can play more kinds of roles. I'm open to whatever people want to call me. I've never really been attracted to men sexually, but I don't think I would be afraid of it if it happened.<ref>{{cite web |url=http://www.glaad.org/eye/brokeback_mountain.php |title=All the latest interviews, reviews and awards for Brokeback Mountain |publisher=[[Gay & Lesbian Alliance Against Defamation|GLAAD]] |access-date=September 19, 2006 |archive-url=https://web.archive.org/web/20061002020344/http://www.glaad.org/eye/brokeback_mountain.php |archive-date=October 2, 2006 |url-status=dead}}</ref>}}

Gyllenhaal narrated the 2005 short animated film ''[[The Man Who Walked Between the Towers]]'',<ref>{{Cite web |last=Cochrane |first=Brian |date=September 3, 2008 |title='Man on Wire' adds related short |url=https://variety.com/2008/film/markets-festivals/man-on-wire-adds-related-short-1117991477/ |url-status=live |access-date=April 7, 2021 |website=[[Variety (magazine)|Variety]] |archive-date=October 30, 2020 |archive-url=https://web.archive.org/web/20201030192449/https://variety.com/2008/film/markets-festivals/man-on-wire-adds-related-short-1117991477/}}</ref> based on [[Mordicai Gerstein]]'s book of the same name about [[Philippe Petit]]'s famous stunt.<ref>{{Cite web |date=January 22, 2007 |title=Willems, Weston Woods win 2007 Carnegie Medal for "Knuffle Bunny" |url=https://www.ala.org/news/news/pressreleases2007/january2007/carnegie07 |access-date=September 19, 2006 |publisher=[[American Library Association]] |language=en |archive-date=January 21, 2025 |archive-url=https://web.archive.org/web/20250121205714/https://www.ala.org/news/news/pressreleases2007/january2007/carnegie07 |url-status=live }}</ref> In January 2007, as host of ''[[Saturday Night Live]]'', he put on a sparkly evening dress and sang "[[And I Am Telling You I'm Not Going]]" from the musical ''[[Dreamgirls]]'' for his opening monologue,<ref>{{cite news |magazine=Edge |date=January 17, 2007 |url=https://www.edgemedianetwork.com/news/national//31150 |title=YouTube Extras: Jake as Effie, and a Musical "Scrubs" |access-date=January 27, 2007 |archive-url=https://web.archive.org/web/20170806180423/https://www.edgemedianetwork.com/news/national//31150 |archive-date=August 6, 2017 |url-status=live}}</ref> dedicating the song to his "unique fan base... the fans of ''Brokeback''".<ref>{{cite web |url=http://www.dailymotion.com/relevance/search/jake+gyllenhaal/video/xzovb_jake-gyllenhaal-sings_events |title=Saturday Night Live Opening Monologue |url-status=dead |archive-url=https://web.archive.org/web/20070930015224/http://www.dailymotion.com/relevance/search/jake%2Bgyllenhaal/video/xzovb_jake-gyllenhaal-sings_events |archive-date=September 30, 2007}}</ref> Later, Gyllenhaal starred in [[David Fincher]]'s mystery thriller ''[[Zodiac (film)|Zodiac]]'' (2007), based on the [[Zodiac Killer]]. He played [[Robert Graysmith]], a ''[[San Francisco Chronicle]]'' political cartoonist.<ref>{{cite web |last1=Mottram |first1=James |date=December 11, 2005 |url=http://www.sundayherald.com/53241 |title=Jake's Progress |work=Sunday Herald |access-date=September 19, 2006 |archive-url=https://web.archive.org/web/20060101194436/http://www.sundayherald.com/53241 |archive-date=January 1, 2006 |url-status=dead}}</ref> In preparation for his role, Gyllenhaal met Graysmith, and videotaped him to study his mannerisms and behavior.<ref>{{cite news |title=''Zodiac'' Production Notes |publisher=[[Paramount Pictures]] Press Kit |year=2007 |url=http://media.movieweb.com/galleries/3158/notes.pdf |archive-url=https://web.archive.org/web/20070927225954/http://media.movieweb.com/galleries/3158/notes.pdf |archive-date=September 27, 2007 |access-date=September 24, 2008 |url-status=dead}}</ref> The film received a positive response; writing for ''[[The Sydney Morning Herald]]'', Paul Byrnes opined that it was "poignant, provocative and haunting", and called Gyllenhaal "terrific".<ref>{{Cite web |title=Zodiac |url=https://www.smh.com.au/entertainment/movies/zodiac-20070519-gdq6a8.html |last=Byrnes |first=Paul |date=May 18, 2007 |website=[[The Sydney Morning Herald]] |url-status=live |archive-url=https://web.archive.org/web/20201101105130/https://www.smh.com.au/entertainment/movies/zodiac-20070519-gdq6a8.html |archive-date=November 1, 2020 |access-date=May 18, 2020}}</ref> He next starred opposite [[Meryl Streep]], [[Alan Arkin]] and [[Reese Witherspoon]] in 2007's ''[[Rendition (film)|Rendition]]'', a [[Gavin Hood]]-directed political thriller about the U.S. policy of [[extraordinary rendition]].<ref>{{Cite web |last1=McNary |first1=Dave |last2=Fleming |first2=Michael |date=September 27, 2006 |title=New Line renders cast |url=https://variety.com/2006/film/markets-festivals/new-line-renders-cast-1117950781/ |access-date=March 15, 2025 |website=[[Variety (magazine)|Variety]] |language=en-US |archive-date=March 1, 2020 |archive-url=https://web.archive.org/web/20200301025945/https://variety.com/2006/film/markets-festivals/new-line-renders-cast-1117950781/ |url-status=live }}</ref> Although it garnered a mixed response, ''[[New York (magazine)|New York]]'' magazine's [[David Edelstein]] called Gyllenhaal "compelling ... he's a reticent actor. But he builds that limitation into the character".<ref>{{Cite web |title=Rendition - Gone Baby Gone - Terror's Advocate -- New York Magazine Movie Review |url=https://nymag.com/movies/reviews/39315/ |last1=Edelstein |first1=David |author-link1=David Edelstein |date=October 12, 2007 |website=[[New York (magazine)|New York]] |url-status=live |archive-url=https://web.archive.org/web/20190609122501/http://nymag.com/movies/reviews/39315/ |archive-date=June 9, 2019 |access-date=May 18, 2020}}</ref> Two years later, he co-starred with Tobey Maguire and [[Natalie Portman]] in [[Jim Sheridan]]'s ''[[Brothers (2009 film)|Brothers]]'', a 2009 remake of [[Susanne Bier]]'s Danish film [[Brothers (2004 film)|of the same name]].<ref>{{cite news |last=Siegel |first=Tatiana |date=October 2, 2007 |url=https://variety.com/2007/film/markets-festivals/natalie-portman-to-star-in-brothers-2-1117973231/ |title=Natalie Portman to star in 'Brothers' |work=Variety |access-date=February 29, 2020 |archive-url=https://web.archive.org/web/20071011002807/http://www.variety.com/article/VR1117973231.html?categoryid=13&cs=1 |archive-date=October 11, 2007 |url-status=live}}</ref> It was met with mixed reviews and moderate box office returns, but Anthony Quinn of ''[[The Independent]]'' thought Gyllenhaal and Maguire gave "honest performances".<ref>{{Cite web |title=Brothers (15) |url=http://www.independent.co.uk/arts-entertainment/films/reviews/brothers-15-1875072.html |last=Quinn |first=Anthony |date=January 22, 2010 |website=[[The Independent]] |url-status=live |archive-url=https://web.archive.org/web/20171219055322/http://www.independent.co.uk/arts-entertainment/films/reviews/brothers-15-1875072.html |archive-date=December 19, 2017 |access-date=May 20, 2020}}</ref> Gyllenhaal has also claimed that Maguire's performance in the film influenced his acting throughout his career.<ref>{{cite web |first=Ryan |last=Northrup |date=February 18, 2022 |url=https://screenrant.com/brothers-movie-tobey-maguire-jake-gyllenhaal-influence-how/ |title=How Tobey Maguire Influenced Jake Gyllenhaal while Filming ''Brothers'' |work=[[Screen Rant]] |access-date=February 19, 2022 |archive-date=July 18, 2022 |archive-url=https://web.archive.org/web/20220718025233/https://screenrant.com/brothers-movie-tobey-maguire-jake-gyllenhaal-influence-how/amp/ |url-status=live}}</ref>

The following year, Gyllenhaal played the lead role in ''[[Prince of Persia: The Sands of Time (film)|Prince of Persia: The Sands of Time]]'', an adaptation of the video game [[Prince of Persia: The Sands of Time|of the same name]], produced by [[Jerry Bruckheimer]] and released by [[Disney]]. He starred opposite [[Anne Hathaway]] in the romantic-comedy'' [[Love & Other Drugs]]'', released on November 24, 2010, which gained him a Golden Globe Award nomination.<ref>{{Cite web |title=Jake Gyllenhaal |url=https://www.goldenglobes.com/person/jake-gyllenhaal |publisher=[[Hollywood Foreign Press Association]] |access-date=May 20, 2020 |archive-url=https://web.archive.org/web/20191207211438/https://www.goldenglobes.com/person/jake-gyllenhaal |archive-date=December 7, 2019 |url-status=live}}</ref> ''[[The Guardian]]''{{'s}} [[Philip French]] welcomed Gyllenhaal's choice of a comic role, in contrast to his previous film roles, but thought the film "stumbles badly".<ref>{{Cite news |last=French |first=Philip |date=January 2, 2011 |title=Love & Other Drugs – review |work=The Observer |url=https://www.theguardian.com/film/2011/jan/02/love-other-drugs-philip-french-review |access-date=May 20, 2020 |issn=0029-7712 |archive-url=https://web.archive.org/web/20190430074725/https://www.theguardian.com/film/2011/jan/02/love-other-drugs-philip-french-review |archive-date=April 30, 2019 |url-status=live}}</ref> For his sole project in 2011, he portrayed Colter Stevens, a [[United States Army Aviation Branch|U.S. Army Aviation]] captain, in the 2011 time-travel thriller ''[[Source Code (film)|Source Code]]''. Despite noting the film's unrealistic plot, Peter Howell of the ''[[Toronto Star]]'' praised the prime performances of the cast.<ref>{{Cite web |title=Source Code: Groundhog doomsday |url=https://www.thestar.com/entertainment/2011/03/31/source_code_groundhog_doomsday.html |last=Howell |first=Peter |date=March 31, 2011 |website=Toronto Star |url-status=live |archive-url=https://web.archive.org/web/20200428181459/https://www.thestar.com/entertainment/2011/03/31/source_code_groundhog_doomsday.html |archive-date=April 28, 2020 |access-date=May 20, 2020}}</ref>

===2012–2018: Critical acclaim and Broadway debut===
Gyllenhaal starred alongside [[Michael Peña]] in [[David Ayer]]'s action thriller ''[[End of Watch]]'', about two Los Angeles street cops. The film, for which Gyllenhaal was also an executive producer, was released in September 2012 and received positive reviews, with [[Roger Ebert]] deeming it "one of the best police movies in recent years, a virtuoso fusion of performances and often startling action" and ''[[Salon (website)|Salon]]''{{'}}s Andrew O'Hehir stating that the film was "at least the best cop movie since [[James Gray (director)|James Gray]]'s ''[[We Own the Night (film)|We Own the Night]]'', and very likely since [[Antoine Fuqua]]'s memorable ''[[Training Day]]'' (which, not coincidentally, was written by Ayer)".<ref>{{cite web |url=https://www.rogerebert.com/reviews/end-of-watch-2012 |title=End of Watch review |date=September 19, 2012 |website=[[RogerEbert.com]] |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730024654/http://www.rogerebert.com/reviews/end-of-watch-2012 |archive-date=July 30, 2017 |url-status=live}}</ref><ref>{{cite web |url=http://www.salon.com/2012/09/20/pick_of_the_week_an_all_time_cop_movie_classic/ |title=Pick of the Week: An All-Time Cop Movie Classic |date=September 20, 2012 |website=[[Salon (website)|Salon]] |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730031414/http://www.salon.com/2012/09/20/pick_of_the_week_an_all_time_cop_movie_classic/ |archive-date=July 30, 2017 |url-status=live}}</ref> To prepare for the role, Gyllenhaal took tactical training and participated in actual police ride-alongs with co-star Peña to help establish the language of the characters.<ref>{{cite web |url=http://www.hitfix.com/in-contention/jake-gyllenhaal-on-building-character-with-language-off-broadway-and-in-end-of-watch |title=Jake Gyllenhaal on building character with language off Broadway and in ''End of Watch'' |date=November 30, 2012 |work=[[HitFix]] |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20160303225956/http://www.hitfix.com/in-contention/jake-gyllenhaal-on-building-character-with-language-off-broadway-and-in-end-of-watch |archive-date=March 3, 2016 |url-status=live}}</ref>

[[File:Jake Gyllenhaal 2012.jpg|thumb|upright|left|Gyllenhaal at the [[2012 Berlin International Film Festival]], where he served as a jury member|alt=Gyllenhaal at the 62nd Berlin International Film Festival, 2012]]

He served as a jury member for the [[62nd Berlin International Film Festival]] that was held in February 2012.<ref>{{cite web |title=Berlinale 2012: International Jury |url=http://www.berlinale.de/en/presse/pressemitteilungen/alle/Alle-Detail_11861.html |date=December 19, 2011 |publisher=[[Berlin International Film Festival]] |url-status=dead |archive-url=https://web.archive.org/web/20120118192826/http://www.berlinale.de/en/presse/pressemitteilungen/alle/Alle-Detail_11861.html |archive-date=January 18, 2012 |access-date=December 21, 2011}}</ref> Also in 2012, Gyllenhaal made his [[Off-Broadway]] debut in [[Nick Payne]]'s play ''[[If There Is I Haven't Found It Yet]]'' at the [[Roundabout Theatre Company]]'s Laura Pels Theatre.<ref>{{cite news |last=Lemon |first=Brendan |url=https://www.ft.com/content/986fb06a-0639-11e2-bd29-00144feabdc0 |title=If There Is I Haven't Found It Yet |work=[[Financial Times]]|publisher=Laura Pels Theatre, New York  |access-date=September 25, 2012 |archive-url=https://web.archive.org/web/20161009112112/https://www.ft.com/content/986fb06a-0639-11e2-bd29-00144feabdc0 |archive-date=October 9, 2016 |url-status=live}}</ref> 2013 saw Gyllenhaal appear in two films directed by [[Denis Villeneuve]], whom Gyllenhaal describes as "an older brother".<ref>{{cite web |last1=Perez |first1=Rodrigo |title=Jake Gyllenhaal & Denis Villeneuve Push Each Other Into Haunting, Bold New Territory For 'Enemy' |url=https://www.indiewire.com/2013/09/jake-gyllenhaal-denis-villeneuve-push-each-other-into-haunting-bold-new-territory-for-enemy-93980/ |website=[[IndieWire]] |access-date=December 11, 2017 |date=September 6, 2013 |archive-url=https://web.archive.org/web/20171211040952/http://www.indiewire.com/2013/09/jake-gyllenhaal-denis-villeneuve-push-each-other-into-haunting-bold-new-territory-for-enemy-93980/ |archive-date=December 11, 2017 |url-status=live}}</ref> The first, the thriller ''[[Prisoners (2013 film)|Prisoners]]'', starred Gyllenhaal as a detective named Loki in search of the abductor of two young girls. ''[[Rolling Stone]]'' critic [[Peter Travers]] praised Gyllenhaal's "exceptional" performance in the film.<ref>{{cite magazine |last1=Travers |first1=Peter |author-link1=Peter Travers |title='Prisoners' Review |url=https://www.rollingstone.com/movies/reviews/prisoners-20130919 |magazine=[[Rolling Stone]] |access-date=December 11, 2017 |date=September 19, 2013 |archive-url=https://web.archive.org/web/20171212084811/https://www.rollingstone.com/movies/reviews/prisoners-20130919 |archive-date=December 12, 2017 |url-status=live}}</ref> In their second collaboration, Gyllenhaal portrayed the dual role of a history teacher and his [[doppelgänger]] in the thriller ''[[Enemy (2013 film)|Enemy]]''.<ref>{{cite web |last=Armitage |first=Hugh |title=Jake Gyllenhaal for dual 'An Enemy' roles |url=http://www.digitalspy.com/movies/news/a372043/jake-gyllenhaal-for-dual-an-enemy-roles/ |website=[[Digital Spy]] |access-date=July 29, 2017 |date=March 20, 2012 |archive-url=https://web.archive.org/web/20170730022322/http://www.digitalspy.com/movies/news/a372043/jake-gyllenhaal-for-dual-an-enemy-roles/ |archive-date=July 30, 2017 |url-status=live}}</ref> The following year, he produced and starred in the crime thriller ''[[Nightcrawler (film)|Nightcrawler]]'', earning Golden Globe Award and [[Screen Actors Guild Award]] nominations for his performance.<ref>{{cite news |last=Buckley |first=Cara |title=On the Scent of Jake Gyllenhaal |url=http://carpetbagger.blogs.nytimes.com/2014/12/16/on-the-scent-of-jake-gyllenhaal/ |access-date=July 30, 2017 |author2=(Carpbetblogger) |work=[[The New York Times]] |date=December 16, 2014 |archive-url=https://web.archive.org/web/20170807112238/https://carpetbagger.blogs.nytimes.com/2014/12/16/on-the-scent-of-jake-gyllenhaal/ |archive-date=August 7, 2017 |url-status=live}}</ref> Ben Sachs of the ''[[Chicago Reader]]'' called Gyllenhaal's performance "attention-grabbing" and said that he "creates a memorable screen presence".<ref>{{Cite web |title=In Nightcrawler, if it bleeds, it leads |url=https://www.chicagoreader.com/chicago/nightcrawler-jake-gyllenhaal-dan-gilroy-rene-russo-tv-news/Content?oid=15485662 |last=Sachs |first=Ben |date=October 29, 2014 |website=[[Chicago Reader]] |url-status=live |archive-url=https://web.archive.org/web/20171127234827/https://www.chicagoreader.com/chicago/nightcrawler-jake-gyllenhaal-dan-gilroy-rene-russo-tv-news/Content?oid=15485662 |archive-date=November 27, 2017 |access-date=May 20, 2020}}</ref>

Gyllenhaal debuted on [[Broadway theatre|Broadway]] in Payne's ''[[Constellations (play)|Constellations]]'' at the [[Samuel J. Friedman Theatre]] opposite [[Ruth Wilson]], also in her Broadway debut.<ref>{{cite news |last1=Beaumont-Thomas |first1=Ben |url=https://www.theguardian.com/stage/2014/jun/13/jake-gyllenhaal-broadway-debut-constellations |title=Jake Gyllenhaal to make Broadway debut in ''Constellations'' |work=[[The Guardian]] |date=June 13, 2014 |access-date=July 29, 2017 |archive-url=https://web.archive.org/web/20170730015905/https://www.theguardian.com/stage/2014/jun/13/jake-gyllenhaal-broadway-debut-constellations |archive-date=July 30, 2017 |url-status=live}}</ref> The production opened in January 2015 and closed in March of the same year.<ref>{{cite web |last1=Brantley |first1=Ben |author-link1=Ben Brantley |url=https://www.nytimes.com/2015/01/14/theater/constellations-with-jake-gyllenhaal-and-ruth-wilson-opens-on-broadway.html |title='Constellations,' With Jake Gyllenhaal and Ruth Wilson, Opens on Broadway |work=[[The New York Times]] |date=January 13, 2015 |access-date=October 21, 2020 |archive-url=https://web.archive.org/web/20190626205910/https://www.nytimes.com/2015/01/14/theater/constellations-with-jake-gyllenhaal-and-ruth-wilson-opens-on-broadway.html |archive-date=June 26, 2019 |url-status=live}}</ref> That same year, he starred in the comedy ''[[Accidental Love]]'', which was filmed in [[South Carolina]] with [[Jessica Biel]], as well as Antoine Fuqua's sports drama ''[[Southpaw (film)|Southpaw]]''.<ref>{{cite news |last=Hambrick |first=Greg |date=March 3, 2008 |title=SC Statehouse to Double as Capitol Hill; Gyllenhaal and Biel to Star |work=Charleston City Paper |url=https://m.charlestoncitypaper.com/PressTime/archives/2008/03/03/sc-statehouse-to-double-as-capitol-hill-gyllenhaal-and-biel-to-star |url-status=live |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730075849/https://m.charlestoncitypaper.com/PressTime/archives/2008/03/03/sc-statehouse-to-double-as-capitol-hill-gyllenhaal-and-biel-to-star |archive-date=July 30, 2017}}</ref><ref>{{cite web |last=Zeitchik |first=Steven |title=For ''Southpaw'' director Antoine Fuqua, a different kind of bout |url=https://www.latimes.com/entertainment/movies/moviesnow/la-et-mn-southpaw-movie-boxing-antoine-fuqua-jake-gyllenhaal-20150724-story.html |work=[[Los Angeles Times]] |access-date=July 30, 2017 |date=July 24, 2015 |archive-url=https://web.archive.org/web/20170730023708/http://www.latimes.com/entertainment/movies/moviesnow/la-et-mn-southpaw-movie-boxing-antoine-fuqua-jake-gyllenhaal-20150724-story.html |archive-date=July 30, 2017 |url-status=live}}</ref> Writing for ''The Independent'', Geoffrey Macnab called his portrayal of a boxer in ''Southpaw'' "plausible" and complimented his "emotional vulnerability", despite an unoriginal plot.<ref>{{Cite web |title=Southpaw is predictably absurd and unoriginal - review |url=http://www.independent.co.uk/arts-entertainment/films/reviews/southpaw-film-review-absurd-and-unoriginal-but-rousingly-entertaining-10409794.html |last=Macnab |first=Geoffrey |date=July 23, 2015 |website=[[The Independent]] |url-status=live |archive-url=https://web.archive.org/web/20171207145234/http://www.independent.co.uk/arts-entertainment/films/reviews/southpaw-film-review-absurd-and-unoriginal-but-rousingly-entertaining-10409794.html |archive-date=December 7, 2017 |access-date=May 20, 2020}}</ref> He then portrayed [[Scott Fischer]] in [[Baltasar Kormákur]]'s ''[[Everest (2015 film)|Everest]]'', based on the [[1996 Mount Everest disaster]];<ref>{{cite news |last=Pulver |first=Andrew |title=''Everest'': how Jake Gyllenhaal got to grips with the world's highest mountain |url=https://www.theguardian.com/film/2015/sep/02/everest-how-jake-gyllenhaal-got-to-grips-with-the-worlds-highest-mountain |work=[[The Guardian]] |access-date=July 30, 2017 |date=September 2, 2015 |archive-url=https://web.archive.org/web/20170730021254/https://www.theguardian.com/film/2015/sep/02/everest-how-jake-gyllenhaal-got-to-grips-with-the-worlds-highest-mountain |archive-date=July 30, 2017 |url-status=live}}</ref> the film was a commercial success, grossing $203&nbsp;million worldwide.<ref>{{Cite web |title=Everest |url=https://www.boxofficemojo.com/release/rl525370881/ |website=Box Office Mojo |access-date=May 20, 2020 |archive-url=https://web.archive.org/web/20200222035303/https://www.boxofficemojo.com/release/rl525370881/ |archive-date=February 22, 2020 |url-status=live}}</ref> Finally, he appeared in [[Jean-Marc Vallée]]'s comedy-drama ''[[Demolition (2015 film)|Demolition]]'', playing an [[Investment banking|investment banker]] Davis Mitchell, who rebuilds his life after losing his wife.<ref>{{Cite news |last=Holden |first=Stephen |title=Review: In ''Demolition'', It's Hammer Time for Jake Gyllenhaal |url=https://www.nytimes.com/2016/04/08/movies/demolition-review-jake-gyllenhaal.html |work=[[The New York Times]] |access-date=July 30, 2017 |date=April 7, 2016 |archive-url=https://web.archive.org/web/20170730022147/https://www.nytimes.com/2016/04/08/movies/demolition-review-jake-gyllenhaal.html |archive-date=July 30, 2017 |url-status=live}}</ref> ''[[The Village Voice]]''{{'}}s Bilge Ebiri praised his performance, writing, "He nails Davis's boyish curiosity, the quiet, wide-eyed uncertainty of someone discovering the world for the first time."<ref>{{Cite web |title=In 'Demolition,' a Finance Bro Finally Gets Hands-On and Feels Something |url=https://www.villagevoice.com/2016/04/07/in-demolition-a-finance-bro-finally-gets-hands-on-and-feels-something/ |last1=Ebiri |first1=Bilge |date=April 7, 2016 |website=[[The Village Voice]] |url-status=dead |archive-url=https://web.archive.org/web/20171204154620/https://www.villagevoice.com/2016/04/07/in-demolition-a-finance-bro-finally-gets-hands-on-and-feels-something/ |archive-date=December 4, 2017 |access-date=May 20, 2020}}</ref> He also served as a jury member for the main competition of the [[2015 Cannes Film Festival]].<ref>{{cite web |url=http://www.festival-cannes.fr/en/article/61318.html |title=The Jury of the 68th Cannes Film Festival |work=Festival de Cannes |date=April 21, 2015 |publisher=[[Cannes Film Festival]] |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20161104191841/http://www.festival-cannes.fr/en/article/61318.html |archive-date=November 4, 2016 |url-status=live}}</ref><ref>{{cite web |url=https://www.thewrap.com/jake-gyllenhaal-sienna-miller-and-guillermo-del-toro-join-cannes-film-festival-jury/ |last=Gilman |first=Greg |title=Jake Gyllenhaal, Sienna Miller and Guillermo del Toro Join Cannes Film Festival Jury |access-date=July 30, 2017 |work=[[TheWrap]] |date=April 21, 2015 |archive-url=https://web.archive.org/web/20170629125401/http://www.thewrap.com/jake-gyllenhaal-sienna-miller-and-guillermo-del-toro-join-cannes-film-festival-jury/ |archive-date=June 29, 2017 |url-status=live}}</ref>

In 2016, he starred in [[Tom Ford]]'s neo-noir thriller ''[[Nocturnal Animals]]'', based on the 1993 novel ''[[Tony and Susan]]'' by [[Austin Wright]].<ref name="McNary-2016">{{cite web |last=McNary |first=Dave |title=Jake Gyllenhaal's ''Nocturnal Animals'' Lands Awards Season Release Date |url=https://variety.com/2016/film/news/jake-gyllenhaal-nocturnal-animals-release-date-1201784012/ |website=[[Variety (magazine)|Variety]] |access-date=July 30, 2017 |date=May 26, 2016 |archive-url=https://web.archive.org/web/20170730014011/http://variety.com/2016/film/news/jake-gyllenhaal-nocturnal-animals-release-date-1201784012/ |archive-date=July 30, 2017 |url-status=live}}</ref> The film received positive reviews.<ref>{{cite web |last1=Sharf |first1=Zack |url=https://www.indiewire.com/2016/09/nocturnal-animals-trailer-tom-ford-jake-gyllenhaal-and-amy-adams-1201724768/ |title=Nocturnal Animals Trailer: Tom Ford Directs Jake Gyllenhaal & Amy Adams |website=[[IndieWire]] |date=September 15, 2016 |access-date=October 21, 2020 |archive-url=https://web.archive.org/web/20190411160922/https://www.indiewire.com/2016/09/nocturnal-animals-trailer-tom-ford-jake-gyllenhaal-and-amy-adams-1201724768/ |archive-date=April 11, 2019 |url-status=dead}}</ref> ''The Sydney Morning Herald''{{'}}s [[Sandra Hall (writer)|Sandra Hall]] praised Gyllenhaal's brilliant portrayal of his two roles, while [[Justin Chang]] of the ''Los Angeles Times'' wrote that his performance contained "rich emotional shadings" and escalating intensity that becomes overwhelming.<ref>{{cite web |last1=Hall |first1=Sandra |author-link=Sandra Hall (writer) |url=http://www.smh.com.au/entertainment/movies/nocturnal-animals-review-story-within-a-story-becomes-unsettling-mind-puzzle-20161031-gsefwf.html |title=Nocturnal Animals review: Story within a story becomes unsettling mind puzzle |work=[[The Sydney Morning Herald]] |date=November 6, 2016 |access-date=June 14, 2021 |archive-url=https://web.archive.org/web/20171203134228/http://www.smh.com.au/entertainment/movies/nocturnal-animals-review-story-within-a-story-becomes-unsettling-mind-puzzle-20161031-gsefwf.html |archive-date=December 3, 2017 |url-status=live}}</ref><ref>{{Cite web |title=Review: Tom Ford's skillful meta-thriller 'Nocturnal Animals' revisits a broken marriage |url=https://www.latimes.com/entertainment/movies/la-et-mn-nocturnal-animals-review-20161114-story.html |last1=Chang |first1=Justin |author-link1=Justin Chang |date=November 17, 2016 |website=[[Los Angeles Times]] |url-access=limited |url-status=live |archive-url=https://web.archive.org/web/20191230210347/https://www.latimes.com/entertainment/movies/la-et-mn-nocturnal-animals-review-20161114-story.html |archive-date=December 30, 2019 |access-date=May 20, 2020}}</ref> In October 2016, he appeared in four benefit concert performances of the [[Stephen Sondheim]] and [[James Lapine]] musical ''[[Sunday in the Park with George]]'' at the [[New York City Center]] as the titular character.<ref>{{cite news |last=Paulson |first=Michael |url=https://www.nytimes.com/2016/07/15/theater/sunday-in-the-park-with-george-with-jake-gyllenhaal-adds-2-performances.html |title=''Sunday in the Park with George'', with Jake Gyllenhaal, Adds 2 Performances |work=[[The New York Times]] |date=July 14, 2016 |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730064202/https://www.nytimes.com/2016/07/15/theater/sunday-in-the-park-with-george-with-jake-gyllenhaal-adds-2-performances.html |archive-date=July 30, 2017 |url-status=live}}</ref> Alexis Soloski of ''The Guardian'' gave the performance a perfect five-star review and hailed Gyllenhaal's superb singing.<ref>{{cite web |last1=Soloski |first1=Alexis |url=https://www.theguardian.com/stage/2016/oct/27/sunday-in-the-park-with-george-review-jake-gyllenhall-sondheim |title=Sunday in the Park With George review – Gyllenhaal sings Sondheim superbly |work=[[The Guardian]] |date=October 27, 2016 |access-date=October 21, 2020 |archive-url=https://web.archive.org/web/20201101105129/https://www.theguardian.com/stage/2016/oct/27/sunday-in-the-park-with-george-review-jake-gyllenhall-sondheim |archive-date=November 1, 2020 |url-status=live}}</ref> Starting in February 2017, Gyllenhaal reprised the role at the reopened [[Hudson Theatre]] on Broadway.<ref name="Brantley-2017">{{cite web |last1=Brantley |first1=Ben |author-link1=Ben Brantley |url=https://www.nytimes.com/2017/02/23/theater/review-sunday-in-the-park-with-george-jake-gyllenhaal.html |title=Review: 'Sunday in the Park With George,' a Living Painting to Make You See |work=[[The New York Times]] |date=February 23, 2017 |access-date=October 21, 2020 |archive-url=https://web.archive.org/web/20190702174713/https://www.nytimes.com/2017/02/23/theater/review-sunday-in-the-park-with-george-jake-gyllenhaal.html |archive-date=July 2, 2019 |url-status=live}}</ref> [[Ben Brantley]] of ''[[The New York Times]]'' praised his "searing theatrical presence, in which his eyes are his center of gravity."<ref name="Brantley-2017"/> He was scheduled to appear in [[Lanford Wilson]]'s ''[[Burn This]]'' on Broadway under the direction of [[Michael Mayer (director)|Michael Mayer]] in 2017.<ref>{{cite web |last1=Paulson |first1=Michael |url=https://www.nytimes.com/2016/10/22/theater/jake-gyllenhaal-broadway-burn-this.html |title=Jake Gyllenhaal on His Return to Broadway: Not So Fast |work=[[The New York Times]] |date=October 22, 2016 |access-date=October 21, 2020 |archive-url=https://web.archive.org/web/20190503025507/https://www.nytimes.com/2016/10/22/theater/jake-gyllenhaal-broadway-burn-this.html |archive-date=May 3, 2019 |url-status=live}}</ref> However, a new production of ''Burn This'' took place in 2019 with [[Adam Driver]] appearing, with Gyllenhaal's production having reportedly been abandoned.<ref>{{cite news |last1=Cox |first1=Gordon |title=Adam Driver to Star in 'Burn This' on Broadway |url=https://variety.com/2017/legit/news/adam-driver-burn-this-broadway-1202640123/ |access-date=August 6, 2018 |work=[[Variety (magazine)|Variety]] |date=December 14, 2017 |archive-url=https://web.archive.org/web/20180803233215/https://variety.com/2017/legit/news/adam-driver-burn-this-broadway-1202640123/ |archive-date=August 3, 2018 |url-status=live}}</ref>

In 2017, Gyllenhaal starred as astronaut David Jordan in the science fiction horror film ''[[Life (2017 film)|Life]]'';<ref name="McNary-2016" /> ''[[Slant Magazine]]''{{'}}s Eric Henderson stated that Gyllenhaal was "dead behind the eyes from his first scene".<ref>{{Cite web |title=Review: Life |url=https://www.slantmagazine.com/film/life/ |last1=Henderson |first1=Eric |date=March 27, 2017 |website=[[Slant Magazine]] |access-date=May 20, 2020 |archive-date=August 2, 2020 |archive-url=https://web.archive.org/web/20200802070420/https://www.slantmagazine.com/film/life/ |url-status=live}}</ref> He also had a supporting role in the action-adventure film ''[[Okja]]'' and starred in the drama ''[[Stronger (film)|Stronger]]'', based on [[Boston Marathon bombing]] survivor [[Jeff Bauman]].<ref name="McNary-2016" /> In his review of the latter, ''The Independent''{{'}}s Geoffrey Macnab complimented Gyllenhaal's versatility and "outstanding" portrayal of Bauman.<ref>{{Cite web |title=Film reviews: Stronger, Human Flow, The Dinner, Brigsby Bear, Menashe |url=http://www.independent.co.uk/arts-entertainment/films/reviews/stronger-the-dinner-human-flow-brigsby-bear-menashe-better-watch-out-a8097351.html |last1=Macnab |first1=Geoffrey |date=December 7, 2017 |website=[[The Independent]] |url-status=live |archive-url=https://web.archive.org/web/20180305215750/https://www.independent.co.uk/arts-entertainment/films/reviews/stronger-the-dinner-human-flow-brigsby-bear-menashe-better-watch-out-a8097351.html |archive-date=March 5, 2018 |access-date=May 20, 2020}}</ref> The following year, he co-starred in the drama ''[[Wildlife (film)|Wildlife]]'' opposite [[Carey Mulligan]], in which he plays a father who temporarily abandons his family to take a dangerous job. It is based on the [[Wildlife (novel)|1990 novel of the same name]] by [[Richard Ford]]. Ella Kemp, writing for ''[[Sight & Sound]]'' magazine, praised the chemistry of the lead actors which "fizzes with an effortless dynamism".<ref>{{Cite web |title=Wildlife first look: Paul Dano's film is a picture of suburban sorrow |url=https://www2.bfi.org.uk/news-opinion/sight-sound-magazine/reviews-recommendations/paul-dano-wildlife-carey-mulligan-jake-gyllenhaal-richard-ford-suburban-sorrow |last=Kemp |first=Ella |date=September 26, 2018 |publisher=[[British Film Institute]] |url-status=live |archive-url=https://web.archive.org/web/20200329225337/https://www.bfi.org.uk/news-opinion/sight-sound-magazine/reviews-recommendations/paul-dano-wildlife-carey-mulligan-jake-gyllenhaal-richard-ford-suburban-sorrow |archive-date=March 29, 2020 |access-date=May 20, 2020}}</ref> He also had a role in the Western drama ''[[The Sisters Brothers (film)|The Sisters Brothers]]'' (2018).<ref name="McNary-2016" />

===2019–present: Action and thriller films===
Gyllenhaal reunited with ''Nightcrawler'' director [[Dan Gilroy]] in the thriller film ''[[Velvet Buzzsaw]]'', in which he plays [[art critic]] Mort Vandewalt.<ref>{{cite web |url=https://deadline.com/2017/06/jake-gyllenhaal-rene-russo-dan-gilroy-art-world-genre-spec-script-nightcrawler-1202116659/ |title=Hot Package: 'Nightcrawler's Dan Gilroy, Jake Gyllenhaal, Rene Russo Reteam |website=[[Deadline Hollywood]] |first=Mike Jr. |last=Fleming |date=June 20, 2017 |access-date=March 12, 2018 |archive-url=https://web.archive.org/web/20171001081242/http://deadline.com/2017/06/jake-gyllenhaal-rene-russo-dan-gilroy-art-world-genre-spec-script-nightcrawler-1202116659/ |archive-date=October 1, 2017 |url-status=live}}</ref> The film premiered at the [[2019 Sundance Film Festival]] and was distributed by [[Netflix]]. ''[[Variety (magazine)|Variety]]''{{'}}s Peter Debrudge opined that Gyllenhaal was "relishing another of those cartoonishly camp performances".<ref>{{Cite news |title=Film Review: 'Velvet Buzzsaw' |url=https://variety.com/2019/film/reviews/velvet-buzzsaw-review-sundance-film-review-jake-gyllenhaal-1203120186/ |last1=Debruge |first1=Peter |date=January 28, 2019 |website=[[Variety (magazine)|Variety]] |url-status=live |archive-url=https://web.archive.org/web/20191222014635/https://variety.com/2019/film/reviews/velvet-buzzsaw-review-sundance-film-review-jake-gyllenhaal-1203120186/ |archive-date=December 22, 2019 |access-date=May 20, 2020}}</ref> That same year, Gyllenhaal played [[comic book]] villain [[Mysterio|Mysterio / Quentin Beck]] in the superhero film ''[[Spider-Man: Far From Home]]'', a sequel to ''[[Spider-Man: Homecoming]]'', set within the [[Marvel Cinematic Universe]].<ref>{{cite news |url=https://variety.com/2018/film/news/jake-gyllenhaal-spider-man-2-tom-holland-1202719941/ |title=Jake Gyllenhaal Eyed for Villain Role in 'Spider-Man: Homecoming' Sequel |last=Kroll |first=Justin |work=[[Variety (magazine)|Variety]] |date=May 21, 2018 |access-date=May 21, 2018 |archive-url=https://web.archive.org/web/20180522042658/http://variety.com/2018/film/news/jake-gyllenhaal-spider-man-2-tom-holland-1202719941/ |archive-date=May 22, 2018 |url-status=live}}</ref> It was one of the highest-grossing films of the year.<ref>{{cite web |last1=Sandwell |first1=Ian |url=https://www.digitalspy.com/movies/a30105685/biggest-movies-2019-box-office-highest-grossing/ |title=Biggest movies of 2019 – highest-grossing movies of the year |website=[[Digital Spy]] |date=December 4, 2019 |access-date=April 8, 2021 |archive-url=https://web.archive.org/web/20201106011945/https://www.digitalspy.com/movies/a30105685/biggest-movies-2019-box-office-highest-grossing/ |archive-date=November 6, 2020 |url-status=live}}</ref> He appeared alongside [[Tom Sturridge]] in ''Sea Wall/A Life'', a double bill of [[monologue]]s by Nick Payne and Simon Stephens, at the Hudson Theatre on Broadway in 2019.<ref>{{cite web |last1=Stasio |first1=Marilyn |url=https://variety.com/2019/legit/reviews/sea-wall-a-life-review-jake-gyllenhaal-broadway-1203292445/ |title='Sea Wall/A Life' Review: Jake Gyllenhaal Stars on Broadway |work=[[Variety (magazine)|Variety]] |date=August 8, 2019 |access-date=October 21, 2020 |archive-url=https://web.archive.org/web/20190809025054/https://variety.com/2019/legit/reviews/sea-wall-a-life-review-jake-gyllenhaal-broadway-1203292445/ |archive-date=August 9, 2019 |url-status=live}}</ref> He garnered a [[Tony Award]] nomination for [[Tony Award for Best Actor in a Play|Best Actor in a Play]] for his performance.<ref>{{cite web |url=https://www.tonyawards.com/shows/sea-walla-life/ |title=Sea Wall / A Life |publisher=[[American Theatre Wing]] and [[The Broadway League]] |access-date=October 17, 2020 |archive-date=November 1, 2020 |archive-url=https://web.archive.org/web/20201101105130/https://www.tonyawards.com/shows/sea-walla-life/ |url-status=live}}</ref> Gyllenhaal also lent his voice for the animation ''[[Spirit Untamed]]'' (2021).<ref name="Jorgeson-2022">{{cite web |last1=Jorgeson |first1=Samantha |url=https://www.indiewire.com/2022/06/strange-world-teaser-jake-gyllenhaal-disney-1234730921/ |title=Strange World Teaser: Jake Gyllenhaal Voices Disney Film |publisher=[[IndieWire]] |date=June 6, 2022 |access-date=June 7, 2022 |archive-url=https://web.archive.org/web/20220606145736/https://www.indiewire.com/2022/06/strange-world-teaser-jake-gyllenhaal-disney-1234730921/ |archive-date=June 6, 2022 |url-status=live}}</ref> That same year, he played detective Joe Baylor in the crime thriller ''[[The Guilty (2021 film)|The Guilty]]'', a remake of the [[The Guilty (2018 film)|Danish film of the same name]].<ref>{{Cite web |last=Rechtshaffen |first=Michael |date=September 10, 2021 |title=Jake Gyllenhaal in 'The Guilty': Film Review {{!}} TIFF 2021 |url=https://www.hollywoodreporter.com/movies/movie-reviews/the-guilty-tiff-2021-1235011407/ |access-date=September 13, 2021 |website=[[The Hollywood Reporter]] |archive-date=September 13, 2021 |archive-url=https://web.archive.org/web/20210913192354/https://www.hollywoodreporter.com/movies/movie-reviews/the-guilty-tiff-2021-1235011407/ |url-status=live}}</ref>

In 2022, he starred as a criminal in [[Michael Bay]]'s action thriller ''[[Ambulance (2022 film)|Ambulance]];'' the film received mixed reviews from critics.<ref>{{cite web |last1=Rubin |first1=Rebecca |url=https://variety.com/2022/film/news/sonic-2-box-office-opening-weekend-ambulance-1235225701/ |title=Sonic the Hedgehog 2 to Lead Box Office Over Ambulance and Morbius |work=[[Variety (magazine)|Variety]] |date=April 6, 2022 |access-date=June 7, 2022 |archive-url=https://web.archive.org/web/20220521074931/https://variety.com/2022/film/news/sonic-2-box-office-opening-weekend-ambulance-1235225701/ |archive-date=May 21, 2022 |url-status=live}}</ref> Gyllenhaal also voiced a farmer in the Disney animation ''[[Strange World (film)|Strange World]]''.<ref name="Jorgeson-2022" /><ref>{{Cite web |last=Kelley |first=Aidan |date=September 26, 2022 |title='Strange World': Release Date, Cast, Trailer, and Everything We Know So Far |url=https://collider.com/strange-world-release-date-cast-trailer-jake-gyllenhaal-disney/ |access-date=November 7, 2022 |website=Collider |language=en-US |archive-date=October 2, 2022 |archive-url=https://web.archive.org/web/20221002085555/https://collider.com/strange-world-release-date-cast-trailer-jake-gyllenhaal-disney/ |url-status=live }}</ref> He appeared in [[Guy Ritchie]]'s ''[[Guy Ritchie's The Covenant|The Covenant]]'' (2023) and [[Doug Liman]]'s action film ''[[Road House (2024 film)|Road House]]'' (2024).<ref>{{cite news |last=Wiseman |first=Andreas |url=https://deadline.com/2021/10/jake-gyllenhaal-guy-ritchie-interpreter-war-movie-stx-afm-1234865119/ |title=STX Launches Sales On Guy Ritchie Action Thriller 'The Interpreter' With Jake Gyllenhaal As Stranded Soldier – AFM Hot Package |date=October 29, 2021 |website=[[Deadline Hollywood]] |access-date=February 11, 2022 |archive-date=March 5, 2022 |archive-url=https://web.archive.org/web/20220305025502/https://deadline.com/2021/10/jake-gyllenhaal-guy-ritchie-interpreter-war-movie-stx-afm-1234865119/ |url-status=live}}</ref><ref>{{cite web |url=https://collider.com/road-house-remake-image-production-begins-jake-gyllenahaal-prime-video/ |title=Jake Gyllenhaal-Led 'Road House' Remake Confirms Start of Production With Behind-The-Scene Image |website=Collider |first=Shrishty |last=Mishra |date=August 23, 2022 |access-date=August 24, 2022 |archive-date=August 23, 2022 |archive-url=https://web.archive.org/web/20220823202544/https://collider.com/road-house-remake-image-production-begins-jake-gyllenahaal-prime-video/ |url-status=live }}</ref> Following the success of ''Road House'', his production company, Nine Stories, signed a first-look deal with [[Amazon MGM Studios]].<ref>{{Cite web |last=Lang |first=Brent |date=April 2, 2024 |title=Fresh Off 'Road House,' Amazon MGM Studios Signs First-Look Deal With Jake Gyllenhaal's Nine Stories |url=https://variety.com/2024/film/news/road-house-jake-gyllenhaal-amazon-mgm-studios-first-look-deal-nine-stories-1235957664/ |access-date=April 4, 2024 |website=Variety |language=en-US |archive-date=April 2, 2024 |archive-url=https://web.archive.org/web/20240402160057/https://variety.com/2024/film/news/road-house-jake-gyllenhaal-amazon-mgm-studios-first-look-deal-nine-stories-1235957664/ |url-status=live }}</ref><ref>{{Cite web |last=Lopez |first=Kristen |date=April 2, 2024 |title=Jake Gyllenhaal's Nine Stories Signs First-Look Deal With Amazon MGM Studios |url=https://www.thewrap.com/jake-gyllenhaal-amazon-mgm-deal/ |access-date=April 4, 2024 |website=TheWrap |language=en-US |archive-date=April 3, 2024 |archive-url=https://web.archive.org/web/20240403021647/https://www.thewrap.com/jake-gyllenhaal-amazon-mgm-deal/ |url-status=live }}</ref>
<!-- He is attached to portray film producer [[Robert Evans]] in ''Francis and the Godfather'', a film that chronicles the creation of 1972's ''[[The Godfather]]'', and military airman [[John A. Chapman]] in the film ''Combat Control''.<ref>{{cite web |last1=Fleming |first1=Mike Jr. |url=https://deadline.com/2020/09/the-godfather-making-of-movie-oscar-isaac-francis-coppola-jake-gyllenhaal-robert-evans-barry-levinson-francis-and-the-godfather-1234588678/ |title='The Godfather' Making Of Movie: Barry Levinson Oscar Isaac Francis Coppola Jake Gyllenhaal Robert Evans |website=[[Deadline Hollywood]] |date=September 30, 2020 |access-date=October 21, 2020 |archive-url=https://web.archive.org/web/20201001072322/https://deadline.com/2020/09/the-godfather-making-of-movie-oscar-isaac-francis-coppola-jake-gyllenhaal-robert-evans-barry-levinson-francis-and-the-godfather-1234588678/ |archive-date=October 1, 2020 |url-status=live}}</ref><ref>{{cite web |last1=Kroll |first1=Justin |url=https://deadline.com/2021/03/mgm-combat-control-jake-gyllenhaal-medal-of-valor-winner-tktkt-and-extractions-sam-hargrave-1234718092/ |title=Jake Gyllenhaal And 'Extraction' Director Team On 'Combat Control' |website=[[Deadline Hollywood]] |date=March 19, 2021 |access-date=May 21, 2021 |archive-url=https://web.archive.org/web/20210319193447/https://deadline.com/2021/03/mgm-combat-control-jake-gyllenhaal-medal-of-valor-winner-tktkt-and-extractions-sam-hargrave-1234718092/ |archive-date=March 19, 2021 |url-status=live}}</ref> Gyllenhaal is slated to executive produce and star in ''The Son'', a television miniseries based on [[Jo Nesbø]]'s [[The Son (Nesbø novel)|novel of the same name]].<ref>{{cite web |last1=Otterson |first1=Joe |url=https://variety.com/2020/tv/news/jake-gyllenhaal-the-son-hbo-denis-villeneuve-jonathan-nolan-lisa-joy-1234810979/ |title=Jake Gyllenhaal to Star in HBO Limited Series 'The Son;' Denis Villeneuve, Jonathan Nolan, Lisa Joy to Produce |work=[[Variety (magazine)|Variety]] |date=October 20, 2020 |access-date=October 21, 2020 |archive-url=https://web.archive.org/web/20201021024745/https://variety.com/2020/tv/news/jake-gyllenhaal-the-son-hbo-denis-villeneuve-jonathan-nolan-lisa-joy-1234810979/ |archive-date=October 21, 2020 |url-status=live}}</ref> He is attached to produce and star in the heist thriller ''Cut and Run,'' and a film adaptation of the musical ''[[Fun Home (musical)|Fun Home]]''.<ref>{{cite news |url=https://deadline.com/2022/01/cut-and-run-jake-gyllenhaal-to-star-in-new-republic-pictures-thriller-1234919701/ |title='Cut And Run': New Republic Pictures Wins Rights To Heist Thriller Penned By John Glenn; Jake Gyllenhaal To Produce & Star |date=January 25, 2022 |first=Matt |last=Grobar |work=[[Deadline Hollywood]] |access-date=January 27, 2022 |archive-date=January 27, 2022 |archive-url=https://web.archive.org/web/20220127052520/https://deadline.com/2022/01/cut-and-run-jake-gyllenhaal-to-star-in-new-republic-pictures-thriller-1234919701/ |url-status=live}}</ref><ref>{{Cite web |url=https://www.broadway.com/buzz/198003/jake-gyllenhaal-to-produce-star-in-movie-musical-adaptation-of-fun-home/ |title=Jake Gyllenhaal to Produce & Star in Movie Musical Adaptation of Fun Home |website=[[Broadway.com]] |access-date=April 8, 2020 |archive-url=https://web.archive.org/web/20200318004148/https://www.broadway.com/buzz/198003/jake-gyllenhaal-to-produce-star-in-movie-musical-adaptation-of-fun-home/ |archive-date=March 18, 2020 |url-status=live}}</ref> He is slated to appear in ''Prophet'', a [[Sam Hargrave]]-directed film based on the [[Prophet (character)|Image Comics character]].<ref>{{cite news |url=https://deadline.com/2021/10/prophet-jake-gyllenhaal-to-star-in-sam-hargrave-studio-8-superhero-pic-1234852325/ |title='Prophet': Jake Gyllenhaal To Star In Studio 8 Superhero Pic From Director Sam Hargrave |website=[[Deadline Hollywood]] |last1=Grobar |first1=Matt |date=October 7, 2021 |access-date=February 11, 2022 |archive-url=https://web.archive.org/web/20211007211809/https://deadline.com/2021/10/prophet-jake-gyllenhaal-to-star-in-sam-hargrave-studio-8-superhero-pic-1234852325/ |archive-date=October 7, 2021 |url-status=live}}</ref> Gyllenhaal stars in a [[Road House (2024 film)|remake]] of ''[[Road House (1989 film)|Road House]]'' as a former [[Ultimate Fighting Championship|UFC]] fighter-turned-bouncer. He will star alongside UFC champion [[Conor McGregor]], and the film will be released on [[Amazon Prime]].<ref>{{Cite web |date=August 3, 2022 |title=Conor McGregor to make acting debut in Jake Gyllenhaal's Road House remake |url=https://www.independent.co.uk/arts-entertainment/films/news/conor-mcgregor-road-house-jake-gyllenhaal-b2137467.html |access-date=August 4, 2022 |website=The Independent |language=en}}</ref> -->In 2024 it was announced that Gyllenhaal would return to Broadway playing [[Iago]] in the 2025 revival of [[William Shakespeare]]'s tragedy ''[[Othello]]'' starring opposite [[Denzel Washington]].<ref>{{cite news |url=https://www.nytimes.com/2024/03/06/theater/denzel-washington-jake-gyllenhaal-othello-broadway.html?unlocked_article_code=1.ak0.XrMM.jka7mN-woG4Q |title=Denzel Washington and Jake Gyllenhaal to Lead Broadway 'Othello' |work=The New York Times |date=March 6, 2024 |access-date=March 6, 2024 |last1=Paulson |first1=Michael |archive-date=August 4, 2024 |archive-url=https://web.archive.org/web/20240804042435/https://www.nytimes.com/2024/03/06/theater/denzel-washington-jake-gyllenhaal-othello-broadway.html?unlocked_article_code=1.ak0.XrMM.jka7mN-woG4Q |url-status=live }}</ref> In June 2024, he joined the cast of the upcoming [[Science fiction film|science fiction]] [[Monster movie|monster film]] ''[[The Bride!]]'' in an undisclosed role.<ref>{{cite web |last1=Keegan |first1=Rebecca |date=June 5, 2024 |title=Jake Gyllenhaal Just Wants to Freak Himself Out |url=https://www.hollywoodreporter.com/movies/movie-features/jake-gyllenhaal-interview-presumed-innocent-road-house-othello-1235914641/ |access-date=June 5, 2024 |website=[[The Hollywood Reporter]] |archive-date=June 6, 2024 |archive-url=https://archive.today/20240606070724/https://www.hollywoodreporter.com/movies/movie-features/jake-gyllenhaal-interview-presumed-innocent-road-house-othello-1235914641/ |url-status=live }}</ref>

==Public image==
Gyllenhaal was named one of ''[[People (magazine)|People]]''{{'s}} "50 Most Beautiful People" in 2006.<ref>''People'' Magazine, "50 Most Beautiful People", April 28, 2006.</ref> He was also listed in ''People''{{'s}} "Hottest Bachelors of 2006".<ref>{{Cite web |date=June 9, 2006 |title=10 Things to Love About Jake |url=https://people.com/celebrity/10-things-to-love-about-jake/ |access-date=March 15, 2025 |website=[[People (magazine)|People]] |language=en |archive-date=March 1, 2020 |archive-url=https://web.archive.org/web/20200301025942/https://people.com/celebrity/10-things-to-love-about-jake/ |url-status=live }}</ref> In April 2012, ''Shalom Life'' ranked him number six on its list of "the 50 most talented, intelligent, funny, and gorgeous Jewish men in the world".<ref>{{cite news |url=http://www.shalomlife.com/culture/17032/top-50-hottest-jewish-men-10-1/ |first=Ashley |last=Baylen |title=Top 50 Hottest Jewish Men (10–1) |work=Shalom Life |date=April 20, 2012 |access-date=April 22, 2013 |archive-url=https://web.archive.org/web/20120531055725/http://www.shalomlife.com/culture/17032/top-50-hottest-jewish-men-10-1/ |archive-date=May 31, 2012 |url-status=dead}}</ref> He was ranked number 35 in ''[[Empire (film magazine)|Empire]]''{{'s}} poll of The 100 Sexiest Movie Stars in 2013.<ref>{{Cite web |last=Green |first=Willow |date=October 7, 2013 |title=The 100 Sexiest Movie Stars: The Men |url=https://www.empireonline.com/movies/features/100-sexiest-men/ |url-status=live |access-date=April 7, 2021 |website=[[Empire (magazine)|Empire]] |archive-date=May 13, 2018 |archive-url=https://web.archive.org/web/20180513031120/https://www.empireonline.com/movies/features/100-sexiest-men/}}</ref> In another poll conducted by ''[[Glamour (magazine)|Glamour]]'', Gyllenhaal was selected as one of the Sexiest Men of The Year 2018.<ref>{{Cite web |last=Bayley |first=Leanne |title=Sexiest Man of The Year 2018: Find out who has been crowned the winner |url=https://www.glamourmagazine.co.uk/gallery/sexiest-man-of-the-year-2018 |access-date=April 7, 2021 |website=Glamour UK |date=December 18, 2017 |archive-date=January 24, 2021 |archive-url=https://web.archive.org/web/20210124161917/https://www.glamourmagazine.co.uk/gallery/sexiest-man-of-the-year-2018 |url-status=live}}</ref>

==Personal life==
===Family and relationships===
{{Further|Gyllenhaal family}}
Gyllenhaal's sister Maggie is married to actor [[Peter Sarsgaard]], Gyllenhaal's co-star in ''Jarhead'' and ''Rendition''.<ref>{{Cite magazine |last=Abramovitch |first=Seth |date=April 30, 2012 |title=Maggie Gyllenhaal and Peter Sarsgaard Confirm Birth of Second Daughter |url=https://www.hollywoodreporter.com/news/general-news/maggie-gyllenhaal-peter-sarsgaard-birth-baby-gloria-ray-318076/ |access-date=November 7, 2022 |magazine=The Hollywood Reporter |archive-date=October 17, 2021 |archive-url=https://web.archive.org/web/20211017233810/https://www.hollywoodreporter.com/news/general-news/maggie-gyllenhaal-peter-sarsgaard-birth-baby-gloria-ray-318076/ |url-status=live }}</ref> In December 2006, Gyllenhaal and his sister escaped a fire that destroyed Manka's Inverness Lodge, a famed lodge and restaurant in [[Inverness, California]], at which they were vacationing. The two were among a dozen or so guests who fled after the fire, sparked by a falling tree, broke out at about 3 a.m. Co-owner and celebrity chef Daniel DeLong said the pair were supportive despite having to brave the wind and cold. "Jake was helping me pull things out of the fire," DeLong said.<ref>{{cite web|agency=[[Associated Press]] |date=December 29, 2006 |url=https://www.hollywoodreporter.com/news/gyllenhaals-forced-flee-fire-at-147873 |title=Gyllenhaals forced to flee fire at lodge |magazine=[[The Hollywood Reporter]] |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170731052623/http://www.hollywoodreporter.com/news/gyllenhaals-forced-flee-fire-at-147873 |archive-date=July 31, 2017 |url-status=live}}</ref>

Gyllenhaal has [[godparent]]s whom he describes as "celebrity godparents". Actor and director [[Paul Newman]] was his godfather,<ref name="Farndale-2007">{{cite news |url=https://www.telegraph.co.uk/culture/3668690/Jake-Gyllenhaal-Aggression-is-a-part-of-me.html |title=Jake Gyllenhaal: 'Aggression is a part of me' |last=Farndale |first=Nigel |author-link=Nigel Farndale |date=October 21, 2007 |newspaper=[[The Daily Telegraph]] |access-date=July 30, 2017 |location=London |archive-url=https://web.archive.org/web/20170731195219/http://www.telegraph.co.uk/culture/3668690/Jake-Gyllenhaal-Aggression-is-a-part-of-me.html |archive-date=July 31, 2017 |url-status=live}}</ref> and actress [[Jamie Lee Curtis]] is his godmother.<ref name="Schruers-2005" /><ref name="Farndale-2007" /> Other godparents of unknown status include a gay couple<ref>{{cite news |last=Sumi |first=Glenn |date=December 15, 2005 |title=Jake Gyllenhaal |url=https://nowtoronto.com/news/cover-story/jake-gyllenhaal/ |newspaper=[[Now (newspaper)|Now]] |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20160106195242/https://nowtoronto.com/news/cover-story/jake-gyllenhaal/ |archive-date=January 6, 2016 |url-status=live}}</ref><ref>{{cite web |url=http://www.netribution.co.uk/content/view/86/267/ |title=BAFTA winner Jake Gyllenhaal – Love and war |last=Applebaum |first=Stephen |date=January 27, 2006 |publisher=[[Netribution]] |archive-url=https://web.archive.org/web/20081023160954/http://www.netribution.co.uk/content/view/86/267/ |archive-date=October 23, 2008 |access-date=December 14, 2014 |url-status=dead}}</ref> and cinematographer [[Robert Elswit]].<ref>{{cite news |url=https://www.theguardian.com/film/2014/oct/30/jake-gyllenhaal-nightcrawler-interview |title=Jake Gyllenhaal on Nightcrawler: 'I'm a bit strange, you know?' |last=Barnes |first=Henry |date=October 30, 2014 |newspaper=[[The Guardian]] |access-date=July 29, 2017 |archive-url=https://web.archive.org/web/20170730021159/https://www.theguardian.com/film/2014/oct/30/jake-gyllenhaal-nightcrawler-interview |archive-date=July 30, 2017 |url-status=live}}</ref><ref>{{cite interview |last=Gyllenhaal |first=Jake |subject-link=Jake Gyllenhaal |interviewer=[[Jian Ghomeshi]] |title=Jake Gyllenhaal sees light in the darkness of Nightcrawler |url=http://www.cbc.ca/q/blog/2014/09/10/jake-gyllenhaal-nightcrawler/ |work=[[Q (radio show)|Q]] |location=Toronto |date=September 10, 2014 |access-date=December 14, 2014 |archive-url=https://web.archive.org/web/20141228101811/http://www.cbc.ca/q/blog/2014/09/10/jake-gyllenhaal-nightcrawler/#t=208 |archive-date=December 28, 2014 |url-status=live}}</ref> Gyllenhaal is the godfather of Matilda Rose Ledger (born October 28, 2005), daughter of his ''Brokeback Mountain'' co-stars Heath Ledger and [[Michelle Williams (actress)|Michelle Williams]].<ref>{{Cite web |last=Lipchik |first=Saul |date=April 24, 2022 |title=Meet Matilda Rose Ledger, the late Heath Ledger's only child |url=https://www.scmp.com/magazines/style/celebrity/article/3175199/meet-matilda-rose-ledger-late-heath-ledgers-only-child-16 |access-date=May 27, 2024 |website=South China Morning Post |language=en}}</ref><!--See talk page section "Robert Elswit" from Dec 2014-->

Gyllenhaal began dating actress [[Kirsten Dunst]] in 2002 after his sister Maggie, who starred with Dunst in ''[[Mona Lisa Smile]]'', introduced them; they eventually broke up in 2004 on friendly terms.<ref>{{cite news |title=Gyllenhaal, Dunst call it quits |work=[[USA Today]] |url=https://www.usatoday.com/life/people/2004-07-20-celeb-couples_x.htm |access-date=July 29, 2017 |first=Karen |last=Thomas |date=July 20, 2004 |archive-url=https://web.archive.org/web/20120716032232/http://www.usatoday.com/life/people/2004-07-20-celeb-couples_x.htm |archive-date=July 16, 2012 |url-status=live}}</ref> He dated his ''Rendition'' co-star [[Reese Witherspoon]] from 2007 until 2009.<ref>{{Cite news |title=Reese Witherspoon & Jake Gyllenhaal Get Close |work=[[People (magazine)|People]] |date=April 5, 2007 |url=https://people.com/celebrity/reese-witherspoon-jake-gyllenhaal-get-close/ |access-date=July 29, 2017 |last1=Thomson |first1=Katherine |archive-url=https://web.archive.org/web/20110607150815/https://people.com/celebrity/reese-witherspoon-jake-gyllenhaal-get-close/ |archive-date=June 7, 2011 |url-status=live}}</ref><ref>{{cite web |first1=Ulrica |last1=Wihlborg |first2=Stephen M. |last2=Silverman |title=Reps Claim Jake and Reese Are Still Together |url=https://people.com/celebrity/reps-claim-jake-and-reese-are-still-together/ |date=November 29, 2009 |access-date=February 29, 2020 |work=[[People (magazine)|People]] |archive-url=https://web.archive.org/web/20200301025944/https://people.com/celebrity/reps-claim-jake-and-reese-are-still-together/ |archive-date=March 1, 2020 |url-status=live}}</ref> He dated singer-songwriter [[Taylor Swift]] from October 2010 to January 2011,<ref>{{cite web |last=Hammel |first=Sara |title=Taylor Swift & Jake Gyllenhaal Share a 'Friendly' Brunch in Brooklyn |url=http://people.com/celebrity/taylor-swift-jake-gyllenhaal-share-a-friendly-brunch-in-brooklyn/ |work=[[People (magazine)|People]] |access-date=July 30, 2017 |date=October 25, 2010 |archive-url=https://web.archive.org/web/20170730024451/http://people.com/celebrity/taylor-swift-jake-gyllenhaal-share-a-friendly-brunch-in-brooklyn/ |archive-date=July 30, 2017 |url-status=live}}</ref><ref>{{cite web |last=Hammel |first=Sara |title=Taylor Swift & Jake Gyllenhaal Break Up: Source |url=https://people.com/celebrity/taylor-swift-jake-gyllenhaal-break-up/ |work=[[People (magazine)|People]] |access-date=February 29, 2020 |date=January 4, 2011 |archive-url=https://web.archive.org/web/20200301025941/https://people.com/celebrity/taylor-swift-jake-gyllenhaal-break-up/ |archive-date=March 1, 2020 |url-status=live}}</ref> and model [[Alyssa Miller]] from July to December 2013.<ref>{{cite news |url=https://people.com/sports/jake-gyllenhaal-dating-sports-illustrated-model-alyssa-miller/ |title=Jake Gyllenhaal Takes a Kiss-Filled Bike Ride with SI Model Alyssa Miller |work=[[People (magazine)|People]] |access-date=July 29, 2017 |archive-url=https://web.archive.org/web/20170730024217/http://people.com/sports/jake-gyllenhaal-dating-sports-illustrated-model-alyssa-miller/ |archive-date=July 30, 2017 |url-status=live}}</ref><ref>{{cite news |url=https://www.eonline.com/ca/news/445672/jake-gyllenhaal-girlfriend-alyssa-miller-enjoy-a-day-out-in-new-york |archive-url=https://web.archive.org/web/20130824122803/http://www.eonline.com/news/445672/jake-gyllenhaal-girlfriend-alyssa-miller-enjoy-a-day-out-in-new-york |archive-date=August 24, 2013 |title=Jake Gyllenhaal & Girlfriend Alyssa Miller Enjoy a Day Out in New York |access-date=February 29, 2020 |url-status=live}}</ref> Gyllenhaal has been in a relationship with French model Jeanne Cadieu since late 2018.<ref>{{Cite web |last1=Rice |first1=Nicholas |last2=Merrett |first2=Robyn |date=September 30, 2021 |title=Jake Gyllenhaal and Jeanne Cadieu Make Red Carpet Debut as a Couple at The Lost Daughter Screening |url=https://people.com/movies/jake-gyllenhaal-jeanne-cadieu-make-red-carpet-debut-as-a-couple/ |url-status=live |access-date=December 18, 2021 |website=[[People (magazine)|People]] |archive-date=December 18, 2021 |archive-url=https://web.archive.org/web/20211218204709/https://people.com/movies/jake-gyllenhaal-jeanne-cadieu-make-red-carpet-debut-as-a-couple/}}</ref>

===Political views and other interests===
Gyllenhaal once filmed a commercial for [[Rock the Vote]] and, along with his sister, visited the [[University of Southern California]] to urge students to vote in the [[2004 U.S. presidential election]].<ref>{{cite journal |last=Nichols |first=Kara |date=September 21, 2004 |url=http://digitallibrary.usc.edu/cdm/ref/collection/p15799coll104/id/152127 |title=Celebrities rally voters |journal=The Daily Trojan |volume=153 |issue=20 |access-date=December 13, 2014 |archive-url=https://web.archive.org/web/20141214035637/http://digitallibrary.usc.edu/cdm/ref/collection/p15799coll104/id/152127 |archive-date=December 14, 2014 |url-status=live}}</ref> He also campaigned for [[Democratic Party (United States)|Democratic Party]] presidential nominee [[John Kerry]].<ref>{{cite news |last=Pelleymounter |first=Alison |date=October 28, 2004 |url=http://media.www.spectatornews.com/media/storage/paper218/news/2004/10/28/CampusNews/Celebrity.Politics-784494.shtml?norewrite200608241448&sourcedomain=www.spectatornews.com |title=Star of Donnie Darko visits EC |work=The Spectator |access-date=September 19, 2006 |url-status=dead |archive-url=https://web.archive.org/web/20090212120808/http://media.www.spectatornews.com/media/storage/paper218/news/2004/10/28/CampusNews/Celebrity.Politics-784494.shtml?norewrite200608241448&sourcedomain=www.spectatornews.com |archive-date=February 12, 2009}}</ref> He has said that "it frustrates me when actors talk politics; I'm political and I make choices in my movies that I think are political. I try and say things with what I do. Rightly or wrongly, young actors have all the power."<ref name="Schruers-2005" /> In an interview, he remarked that "it's a sad time when actors are politicians and politicians are actors".<ref>{{cite web |url=http://video.stv.tv/bc/entertainment-entertainment_now-20071019-jake-gyllenhaal-how-do-you-pronounce-that/?redirect=no |title=STV Player |archive-url=https://web.archive.org/web/20120831063613/http://video.stv.tv/bc/entertainment-entertainment_now-20071019-jake-gyllenhaal-how-do-you-pronounce-that/?redirect=no |archive-date=August 31, 2012 |url-status=dead}}</ref> In the [[2018 midterm elections]], Gyllenhaal endorsed [[U.S. Senate]] candidate [[Beto O'Rourke]]. His endorsement came in the form of a [[Facebook]] post that included a picture of him in a "BETO" shirt and a caption that also endorsed [[Stacey Abrams]], [[Andrew Gillum]], [[Kyrsten Sinema]], and [[Jacky Rosen]] in their respective Senate or gubernatorial elections.<ref>{{cite news |last1=Rao |first1=Sonia |url=https://www.washingtonpost.com/arts-entertainment/2018/11/06/beyonc-endorses-beto-orourke-election-day-when-we-are-truly-united-we-are-unstoppable/ |title=Beyoncé endorses Beto O'Rourke on Election Day: 'When we are truly united we are unstoppable' |newspaper=[[The Washington Post]] |date=November 6, 2018 |access-date=October 21, 2020 |archive-url=https://web.archive.org/web/20201024232637/https://www.washingtonpost.com/arts-entertainment/2018/11/06/beyonc-endorses-beto-orourke-election-day-when-we-are-truly-united-we-are-unstoppable/ |archive-date=October 24, 2020 |url-status=dead}}</ref>

Gyllenhaal [[recycles]] regularly, and said in an interview that he spends $400 a year to have trees planted in a [[Mozambique]] forest, partly to promote the Future Forests program.<ref>{{cite web |last=Foley |first=Jack |year=2003 |title=The Day After Tomorrow – Jake Gyllenhaal Q&A |url=http://www.indielondon.co.uk/film/day_after_tomorrow_gyllenhaalQ&A.html |url-status=live |archive-url=https://web.archive.org/web/20170612043613/http://www.indielondon.co.uk/film/day_after_tomorrow_gyllenhaalQ%26A.html |archive-date=June 12, 2017 |access-date=July 30, 2017 |work=Indie London}}</ref><ref>{{cite web |last=Curry |first=Carolann |date=May 27, 2004 |title=2004: The year of Jake Gyllenhaal |url=http://www.geocities.com/youthquakemagazine/actor_articles/jake.htm |url-status=dead |archive-url=https://web.archive.org/web/20040924144857/http://www.geocities.com/youthquakemagazine/actor_articles/jake.htm |archive-date=September 24, 2004 |access-date=August 24, 2006 |website=Youth Quake}}</ref> After filming ''The Day After Tomorrow'', he flew to the [[Arctic]] to promote awareness of [[climate change]].<ref>{{cite news |last=Eilperin |first=Juliet |date=April 26, 2005 |title=Ice Crusade |newspaper=[[The Washington Post]] |url=https://www.washingtonpost.com/wp-dyn/content/article/2005/04/25/AR2005042501579.html |url-status=live |access-date=July 29, 2017 |archive-url=https://web.archive.org/web/20170731224759/http://www.washingtonpost.com/wp-dyn/content/article/2005/04/25/AR2005042501579.html |archive-date=July 31, 2017}}</ref><ref>{{Cite web |date=April 21, 2005 |title=Arctic Wisdom |url=http://arcticwisdom.org/home.shtml |archive-url=https://web.archive.org/web/20050426152425/http://arcticwisdom.org/home.shtml |archive-date=April 26, 2005 |access-date=September 19, 2006 |publisher=Spectral Productions Inc.}}</ref> He has described climate activist [[Greta Thunberg]] as an inspiring figure.<ref>{{Cite news |last=Heawood |first=Sophie |date=September 26, 2021 |title=Jake Gyllenhaal: 'Women? They're superior to men' |work=[[The Sunday Times]] |url=https://www.thetimes.com/article/jake-gyllenhaal-women-theyre-superior-to-men-5pcntxlbg |access-date=January 16, 2022 |issn=0140-0460 |archive-date=January 16, 2022 |archive-url=https://web.archive.org/web/20220116123957/https://www.thetimes.co.uk/article/jake-gyllenhaal-women-theyre-superior-to-men-5pcntxlbg |url-status=live}}</ref>

In 2003, Gyllenhaal participated in an advertising campaign by the [[American Civil Liberties Union]].<ref>{{Cite web |date=September 15, 2003 |title=Celebrities Speak Out for Civil Liberties in New ACLU Advertising Campaign |url=https://www.aclu.org/press-releases/celebrities-speak-out-civil-liberties-new-aclu-advertising-campaign |access-date=September 19, 2006 |publisher=[[American Civil Liberties Union]] |language=en-US}}</ref><ref>{{Cite web |last1=Van Tine |first1=Dennis |last2=Lowery |first2=Jen |last3=Marcus |first3=Bennett |date=October 4, 2005 |title=Open All Night: ACLU Freedom Concert |url=http://www.oanmedia.com/2004/09/aclu_freedom_concert.php |archive-url=https://web.archive.org/web/20160303165052/http://www.oanmedia.com/2004/09/aclu_freedom_concert.php |archive-date=March 3, 2016 |access-date=March 15, 2025 |website=Open All Night}}</ref> Gyllenhaal is the Honorary Chair of the [[New Eyes for the Needy]] Advisory Board,<ref>{{cite news |url=https://www.looktothestars.org/news/9304-jake-gyllenhaal-honored-at-new-eyes-for-the-needy-dinner |title=Jake Gyllenhaal is the Honorary Chair of the New Eyes For The Needy Advisory Board |date=November 21, 2012 |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730014625/https://www.looktothestars.org/news/9304-jake-gyllenhaal-honored-at-new-eyes-for-the-needy-dinner |archive-date=July 30, 2017 |url-status=live}}</ref> and has signed on to help the TV fundraiser [[Stand Up to Cancer]].<ref>{{cite web |url=https://www.tvguide.com/News/Stand-Up-Cancer-1020491.aspx |title=Fox, Jake Gyllenhaal Join Stand Up To Cancer |work=TV Guide |access-date=July 30, 2017 |date=July 13, 2010 |archive-url=https://web.archive.org/web/20140513113754/http://www.tvguide.com/news/stand-up-cancer-1020491.aspx |archive-date=May 13, 2014 |url-status=live}}</ref> Gyllenhaal is on the board of directors for the [[Anti-Recidivism Coalition]] and volunteered in California juvenile detention centers with [[Scott Budnick (film producer)|Scott Budnick]].<ref>{{cite magazine |last=Mechanic |first=Michael |title=Why the Producer of 'The Hangover Part III' Spends So Much Time in Prison |url=https://www.motherjones.com/media/2013/05/hangover-part-iii-executive-producer-scott-budnick-california-prison-interview |magazine=Mother Jones |date=May 23, 2013 |access-date=July 30, 2017 |archive-url=https://web.archive.org/web/20170730075103/http://www.motherjones.com/media/2013/05/hangover-part-iii-executive-producer-scott-budnick-california-prison-interview/ |archive-date=July 30, 2017 |url-status=live}}</ref> In 2014, Gyllenhaal attended an event that benefited the Headstrong Project, an organization that provides treatment to military veterans suffering from [[post traumatic stress disorder]], during which he read a poem by a veteran,<ref>{{cite web |last1=Lewis |first1=Hilary |url=https://www.hollywoodreporter.com/news/general-news/jake-gyllenhaal-anthony-edwards-offer-737830/ |title=Jake Gyllenhaal, Anthony Edwards Offer Words of Support for Military Vets |website=[[The Hollywood Reporter]] |date=October 2, 2014 |access-date=May 21, 2021 |archive-url=https://web.archive.org/web/20210521105848/https://www.hollywoodreporter.com/news/general-news/jake-gyllenhaal-anthony-edwards-offer-737830/ |archive-date=May 21, 2021 |url-status=live}}</ref> and in 2017 he participated in a fundraiser to help survivors who lost limbs during the [[September 11 attacks]] in 2001.<ref>{{cite news |last1=Kitnick |first1=Sara |title=Jake Gyllenhaal, Steve Buscemi and More Take Part in 9/11 Fundraiser |url=https://www.hollywoodreporter.com/lifestyle/lifestyle-news/jake-gyllenhaal-steve-buscemi-more-take-part-9-11-fundraiser-1038045/ |work=[[The Hollywood Reporter]] |date=September 12, 2017 |access-date=May 21, 2021 |archive-url=https://web.archive.org/web/20210514110122/https://www.hollywoodreporter.com/lifestyle/lifestyle-news/jake-gyllenhaal-steve-buscemi-more-take-part-9-11-fundraiser-1038045/ |archive-date=May 14, 2021 |url-status=live}}</ref> Gyllenhaal has studied Buddhism and has said, "I am not a card-carrying Buddhist, but I do try to practice [[Mindfulness (Buddhism)|mindfulness]]" and that it is his goal to meditate every day.<ref>{{cite news |author=Eimer, David |date=May 23, 2004 |title=Jake's Progress |work=[[The Times]] |url=http://entertainment.timesonline.co.uk/tol/arts_and_entertainment/film/article429340.ece |url-status=dead |access-date=September 19, 2006 |archive-url=https://web.archive.org/web/20110615140127/http://entertainment.timesonline.co.uk/tol/arts_and_entertainment/film/article429340.ece |archive-date=June 15, 2011}}</ref><ref>{{cite web |author=Denizet-Lewis, Benoit |url=http://men.style.com/details/features/full?id=content_4026&pageNum=2 |title=Jake |website=Style.com |access-date=September 19, 2006 |archive-url=https://web.archive.org/web/20070930204150/http://men.style.com/details/features/full?id=content_4026&pageNum=2 |archive-date=September 30, 2007 |url-status=dead}}</ref>

==Acting credits and awards==
{{Main|Jake Gyllenhaal on screen and stage|List of awards and nominations received by Jake Gyllenhaal}}

Gyllenhaal's most acclaimed [[Jake Gyllenhaal on screen and stage|films]], according to the review aggregate site Rotten Tomatoes, include ''October Sky'' (1999), ''Donnie Darko'' (2001), ''Lovely & Amazing'' (2002), ''Brokeback Mountain'' (2005), ''Zodiac'' (2007), ''Source Code'' (2011), ''End of Watch'' (2012), ''Nightcrawler'' (2014), and ''Stronger'' (2017). He has received [[List of awards and nominations received by Jake Gyllenhaal|numerous accolades]], including a [[British Academy Film Awards|BAFTA Film Award]], an [[Independent Spirit Award]], and nominations for an [[Academy Award]], three [[Golden Globe Awards]], three [[Screen Actors Guild Awards]] and three [[Tony Awards]].

==References==
{{Reflist}}

==External links==
* {{IMDb name}}
* {{IBDB name}}
* {{IOBDB name}}
* {{Tcmdb name}}
* {{Commons category-inline|Jake Gyllenhaal}}

{{Navboxes
|title = [[List of awards and nominations received by Jake Gyllenhaal|Awards for Jake Gyllenhaal]]
|list =
{{BAFTA Award for Best Supporting Actor 1985–2009}}
{{Desert Palm Achievement Award}}
{{Evening Standard Theatre Award for Outstanding Newcomer}}
{{Houston Film Critics Society Award for Best Actor}}
{{MTV Movie Award for Best Kiss}}
{{MTV Movie Award for Best Performance}}
{{National Board of Review Award for Best Supporting Actor}}
{{San Diego Film Critics Society Award for Best Actor}}
{{St. Louis Gateway Film Critics Association Award for Best Actor}}
{{Vancouver Film Critics Circle Award for Best Actor}}
}}

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{{DEFAULTSORT:Gyllenhaal, Jake}}
[[Category:1980 births]]
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[[Category:American people of Swedish descent]]
[[Category:Best Supporting Actor BAFTA Award winners]]
[[Category:Columbia College, Columbia University alumni]]
[[Category:Gyllenhaal family|Jake]]
[[Category:Harvard-Westlake School alumni]]
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