Jake Gyllenhaal
Jake Gyllenhaal, the American actor born on the 19th of December 1980, came close to playing two of the best-known superheroes in film. In 2003 he auditioned for Batman Begins and nearly won the part, which went to Christian Bale. A year later, director Sam Raimi worried about the health of Tobey Maguire and nearly cast Gyllenhaal as Spider-Man for Spider-Man 2. Maguire recovered, and the sequel was shot without him. The two men look alike enough that Gyllenhaal jokes about cab drivers calling him Spider-Man.
Missing both roles did not slow him down. His career on screen and stage now covers more than three decades. It runs from a cult thriller to a landmark romance, from studio spectacles to the Broadway stage.
How does the son of a film director and a screenwriter build a career like that, when his own parents often refused to let him take parts? What does he do to prepare for the people he plays? And why does he keep returning to the theatre, and to causes far from the cameras?
Stephen Gyllenhaal directed films and Naomi Foner wrote screenplays, and their son Jacob Benjamin Gyllenhaal was born in Los Angeles, California. His older sister, Maggie, also became an actress. Their father was raised a Swedenborgian and descends from the Swedish noble Gyllenhaal family. The last ancestor born in Sweden was his great-great-grandfather, Anders Leonard Gyllenhaal. Their mother was born in New York City into an Ashkenazi Jewish family from Russia and Poland, and Jake has said that he considers himself Jewish.
A lazy eye meant corrective lenses from the age of 6. On his 13th birthday he performed what he called a "Bar Mitzvah-like act, without the typical trappings." He volunteered at a homeless shelter, because his parents wanted him to feel grateful for his privileged life.
In 1991 he made his acting debut in the comedy City Slickers, playing Billy Crystal's son. His parents then turned down The Mighty Ducks in 1992, since the job would have kept him away from home for two months. For years they let him audition but often forbade him from accepting a part he won. Family projects were the exception. He appeared with Maggie in his father's 1993 film A Dangerous Woman, and later in his father's 1998 comedy Homegrown. In 1994 he also played in a Homicide: Life on the Street episode called "Bop Gun." Before his final year of high school, the only other film he was allowed to make was the little-known children's adventure Josh and S.A.M. Jake and Maggie also joined their mother for two episodes of the Food Network cooking show Molto Mario.
His parents insisted on summer jobs, and he worked as a lifeguard and as a busboy at a restaurant run by a family friend. He later reflected on his upbringing. "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."
In 1998 he graduated from the Harvard-Westlake School in Los Angeles. He then went to Columbia University, where Maggie was a senior and where his mother had studied, to read Eastern religions and philosophy. He lived in John Jay Hall and dropped out after two years to concentrate on acting. He has said he still intends to finish the degree.
Joe Johnston's 1999 film October Sky gave Gyllenhaal his first lead role. It adapts Homer Hickam's autobiography Rocket Boys. Gyllenhaal plays a young man from West Virginia who is trying to win a science scholarship so he can avoid life as a coal miner. The film was well received and earned $32 million. The Sacramento News and Review called it his "breakout performance."
Richard Kelly's Donnie Darko followed in 2001, and it failed at the box office on its first release. It later became a cult favorite. The film is set in 1988. Gyllenhaal plays a troubled teenager who sees visions of a 6 ft rabbit named Frank, who tells him the world is coming to an end. Gary Mairs of Culture Vulture praised him. He wrote that Gyllenhaal "manages the difficult trick of seeming both blandly normal and profoundly disturbed, often within the same scene."
The year 2002 brought uneven results. In Highway he played Pilot Kelston alongside Jared Leto, and one critic called his performance "silly, clichéd and straight to video." The Good Girl, opposite Jennifer Aniston, premiered at the 2002 Sundance Film Festival. He also starred in Lovely and Amazing with Catherine Keener. In both films he plays an unstable character who begins a reckless affair with an older woman. He later described these as "teenager in transition" roles.
Bubble Boy, a Touchstone Pictures romantic comedy loosely based on the story of David Vetter, was panned. One critic called it "stupid and devoid of any redeeming features." Moonlight Mile, also from 2002, put him opposite Dustin Hoffman, Susan Sarandon and Ellen Pompeo. He plays a young man coping with the death of his fiancée and the grief of her parents. Reviews were mixed. The story draws on writer-director Brad Silberling's own experience after the murder of his girlfriend, Rebecca Schaeffer.
Ang Lee's Brokeback Mountain, released in 2005, cast Gyllenhaal and Heath Ledger as young sheep herders who meet and begin a sexual relationship in the summer of 1963. It lasts for 20 years. The media often used the shorthand "the gay cowboy movie," though opinion differed on how to describe the characters' sexual orientation.
The film won the Golden Lion at the Venice Film Festival, three Academy Awards and four Golden Globes. It also took four British Academy Film Awards. Gyllenhaal was nominated for the Academy Award for Best Supporting Actor but lost to George Clooney for Syriana. He did win the BAFTA for Best Supporting Actor, and he and Ledger won an MTV Movie Award for Best Kiss in 2006. Shortly after the 2006 Academy Awards, he was invited to join the Academy.
Gyllenhaal had mixed feelings about being directed by Ang Lee. He disliked the way Lee tended to withdraw from his actors once filming began. He still praised the director's encouraging approach and his sensitive handling of the material. At the Directors Guild of America Awards on the 28th of January 2006, he praised Lee for "his humbleness and his respect for everyone around him." Of the kissing scenes with Ledger, he said, "As an actor, I think we need to embrace the times we feel most uncomfortable."
Rumors about his own sexual orientation followed the film's release. He told an interviewer the gossip was flattering, because it suggested he could play more kinds of roles. He added, "I'm open to whatever people want to call me."
Gyllenhaal narrated the 2005 animated short The Man Who Walked Between the Towers, based on Mordicai Gerstein's book about Philippe Petit's famous stunt. In January 2007 he hosted Saturday Night Live and opened in a sparkly evening dress. He sang "And I Am Telling You I'm Not Going" from the musical Dreamgirls and dedicated it to his "unique fan base... the fans of Brokeback."
The friendship outlasted the film. Gyllenhaal is godfather to Matilda Rose Ledger, born on the 28th of October 2005, the daughter of Ledger and fellow Brokeback Mountain co-star Michelle Williams.
For Zodiac in 2007, David Fincher's thriller about the Zodiac Killer, Gyllenhaal played Robert Graysmith, a political cartoonist at the San Francisco Chronicle. He met Graysmith and videotaped him to study his mannerisms and behavior. Paul Byrnes of The Sydney Morning Herald called the film "poignant, provocative and haunting" and Gyllenhaal "terrific."
In 2005 Sam Mendes's Jarhead cast him as a U.S. Marine in the first Gulf War. Stephen Hunter of The Washington Post wrote, "He makes us see his character's intelligence." That year he also appeared in Proof, alongside Gwyneth Paltrow and Anthony Hopkins, as a graduate student in mathematics. His character urges Paltrow's character to publish a revolutionary proof.
Gavin Hood's Rendition, from 2007, is a political thriller about the U.S. policy of extraordinary rendition. Gyllenhaal appeared with Meryl Streep, Alan Arkin and Reese Witherspoon. The response was mixed, but David Edelstein of New York magazine called him "compelling... he's a reticent actor. But he builds that limitation into the character."
Jim Sheridan's Brothers, in 2009, remade Susanne Bier's Danish film of the same name. Gyllenhaal starred with Tobey Maguire and Natalie Portman. Reviews were mixed and the box office moderate, but Anthony Quinn of The Independent thought the two men gave "honest performances." Gyllenhaal has claimed that Maguire's performance in the film influenced his acting throughout his career.
To prepare for David Ayer's End of Watch, released in September 2012, he took tactical training. He also joined real police ride-alongs with co-star Michael Peña to establish the language of the characters, and he served as an executive producer. Roger Ebert called it "one of the best police movies in recent years, a virtuoso fusion of performances and often startling action."
Denis Villeneuve directed two of Gyllenhaal's films in 2013, and the actor describes him as "an older brother." In Prisoners he plays a detective named Loki, who searches for the abductor of two young girls. Peter Travers of Rolling Stone called the performance "exceptional." In Enemy he plays a history teacher and the man's doppelgänger.
In 2014 he produced and starred in the crime thriller Nightcrawler. It earned him nominations for a Golden Globe, an Actor Award and a BAFTA. Many people considered his absence from the Best Actor Oscar category a snub. Ben Sachs of the Chicago Reader called the performance "attention-grabbing."
Nocturnal Animals, Tom Ford's 2016 neo-noir thriller, is based on Austin Wright's 1993 novel Tony and Susan. It brought Gyllenhaal a BAFTA nomination for Best Actor in a Leading Role. In Stronger he plays Boston Marathon bombing survivor Jeff Bauman, and Geoffrey Macnab of The Independent called the portrayal "outstanding." In Wildlife, adapted from Richard Ford's 1990 novel, he plays a father who temporarily abandons his family for a dangerous job. Ella Kemp of Sight & Sound said his chemistry with Carey Mulligan "fizzes with an effortless dynamism."
The Day After Tomorrow, a 2004 science fiction blockbuster, cast Dennis Quaid as Gyllenhaal's father.
In 2010 he led Prince of Persia: The Sands of Time, an adaptation of a video game produced by Jerry Bruckheimer and released by Disney. That year he also starred opposite Anne Hathaway in the romantic comedy Love & Other Drugs, released on the 24th of November 2010. It gained him a Golden Globe nomination. Philip French of The Guardian welcomed the comic role but thought the film "stumbles badly."
Source Code was his only project of 2011. He plays Colter Stevens, a U.S. Army Aviation captain, in a time-travel thriller. Peter Howell of the Toronto Star noted the unrealistic plot but praised the cast.
Baltasar Kormákur's Everest, in 2015, dramatizes the 1996 Mount Everest disaster, with Gyllenhaal as Scott Fischer. It grossed $203 million worldwide. In 2017 he played astronaut David Jordan in the science fiction horror film Life. Eric Henderson of Slant Magazine was harsher, writing that Gyllenhaal was "dead behind the eyes from his first scene."
In 2019 he played the comic book villain Mysterio, also known as Quentin Beck, in Spider-Man: Far From Home. The film is a sequel to Spider-Man: Homecoming and part of the Marvel Cinematic Universe. It was one of the highest-grossing films of the year, and it remains his highest grossing release. That same year he reunited with Nightcrawler director Dan Gilroy for Velvet Buzzsaw, playing the art critic Mort Vandewalt. The film premiered at the 2019 Sundance Film Festival and was distributed by Netflix. Peter Debrudge of Variety said Gyllenhaal was "relishing another of those cartoonishly camp performances."
In 2021 he played the detective Joe Baylor in The Guilty, a remake of a Danish film. He also lent his voice to the animation Spirit Untamed that year. In 2022 he played a criminal in Michael Bay's action thriller Ambulance, which received mixed reviews, and voiced a farmer in the Disney animation Strange World. Guy Ritchie's The Covenant followed in 2023, then Doug Liman's Road House in 2024, alongside the series Presumed Innocent.
The success of Road House led his production company, Nine Stories, to sign a first-look deal with Amazon MGM Studios. In June 2024 he joined the cast of the science fiction monster film The Bride!, in an undisclosed role.
In 2002 Gyllenhaal made his theatrical debut in Kenneth Lonergan's revival of This Is Our Youth at the Garrick Theatre in London. He explained the choice simply: "Every actor I look up to has done theatre work, so I knew I had to give it a try." The play ran for eight weeks in the West End. He won favorable reviews and the Standard Theatre Award for Outstanding Newcomer.
In 2012 he 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. Payne's Constellations then marked his Broadway debut, at the Samuel J. Friedman Theatre. His co-star Ruth Wilson was also making her Broadway debut. The production opened in January 2015 and closed in March of the same year.
In October 2016 he played the title character 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. Alexis Soloski of The Guardian gave it five stars and hailed his singing. In February 2017 he reprised the role at the reopened Hudson Theatre on Broadway. Ben Brantley of The New York Times praised his "searing theatrical presence, in which his eyes are his center of gravity."
Lanford Wilson's Burn This was meant to be his next Broadway project, under the direction of Michael Mayer in 2017. That production was reportedly abandoned. A new production followed in 2019 with Adam Driver.
That same year Gyllenhaal appeared with Tom Sturridge in Sea Wall/A Life, a double bill of monologues by Nick Payne and Simon Stephens, at the Hudson Theatre. It earned him a Tony Award nomination for Best Actor in a Play.
In 2024 it was announced that he would return to Broadway as Iago in the 2025 revival of Shakespeare's tragedy Othello, opposite Denzel Washington.
In December 2006, a fire destroyed Manka's Inverness Lodge, a famed lodge and restaurant in Inverness, California. Gyllenhaal and Maggie were vacationing there. The fire started at about 3 a.m., sparked by a falling tree, and a dozen or so guests fled. Co-owner and celebrity chef Daniel DeLong recalled, "Jake was helping me pull things out of the fire."
Gyllenhaal calls his godparents "celebrity godparents." The actor and director Paul Newman was his godfather, and the actress Jamie Lee Curtis is his godmother. Maggie is married to the actor Peter Sarsgaard, who co-starred with Jake in Jarhead and Rendition.
Kirsten Dunst began dating Gyllenhaal in 2002, after Maggie, who starred with Dunst in Mona Lisa Smile, introduced them. They broke up in 2004 on friendly terms. He dated his Rendition co-star Reese Witherspoon from 2007 until 2009. Since late 2018 he has been in a relationship with the French model Jeanne Cadieu.
In the 2004 U.S. presidential election, Gyllenhaal filmed a commercial for Rock the Vote. With Maggie, he visited the University of Southern California to urge students to vote, and he campaigned for the Democratic nominee, John Kerry. He once said that "it frustrates me when actors talk politics." He added that his movie choices are political in his view, because "I try and say things with what I do." In the 2018 midterms he endorsed Senate candidate Beto O'Rourke in a Facebook post that showed him in a "BETO" shirt. The caption also endorsed Stacey Abrams, Andrew Gillum, Kyrsten Sinema and Jacky Rosen.
He says he spends $400 a year to have trees planted in a Mozambique forest, partly to promote the Future Forests program. After filming The Day After Tomorrow, he flew to the Arctic to promote awareness of climate change. He has described the climate activist Greta Thunberg as an inspiring figure.
In 2003 he took part in an advertising campaign by the American Civil Liberties Union. He is Honorary Chair of the New Eyes for the Needy Advisory Board and has helped the TV fundraiser Stand Up to Cancer. He sits on the board of the Anti-Recidivism Coalition and has volunteered in California juvenile detention centers with Scott Budnick. In 2014 he attended a benefit for the Headstrong Project, which treats military veterans with post traumatic stress disorder, and read a poem by a veteran. In 2017 he joined a fundraiser for survivors who lost limbs in the September 11 attacks.
He has also studied Buddhism. "I am not a card-carrying Buddhist, but I do try to practice mindfulness," he has said, and his goal is to meditate every day.
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Common questions
When was Jake Gyllenhaal born and who are his parents?
Jake Gyllenhaal was born on the 19th of December 1980 in Los Angeles, California. His parents are the film director Stephen Gyllenhaal and the screenwriter Naomi Foner.
What was Jake Gyllenhaal's first film role?
Jake Gyllenhaal made his acting debut in the 1991 comedy City Slickers, playing Billy Crystal's son. His first lead role came in the 1999 film October Sky.
Did Jake Gyllenhaal win an award for Brokeback Mountain?
Jake Gyllenhaal won the BAFTA Award for Best Supporting Actor for Brokeback Mountain (2005). He was also nominated for the Academy Award in the same category but lost to George Clooney for Syriana.
What is Jake Gyllenhaal's highest grossing film?
Spider-Man: Far From Home (2019) is Jake Gyllenhaal's highest grossing release. He played the villain Mysterio, also known as Quentin Beck, in the Marvel Cinematic Universe film.
Has Jake Gyllenhaal been nominated for a Tony Award?
Jake Gyllenhaal was nominated for the Tony Award for Best Actor in a Play for Sea Wall/A Life. He performed the double bill of monologues by Nick Payne and Simon Stephens at the Hudson Theatre on Broadway in 2019.
Which Broadway and West End plays has Jake Gyllenhaal appeared in?
Jake Gyllenhaal starred in This Is Our Youth in London's West End in 2002. On Broadway he has appeared in Constellations, Sunday in the Park with George and Sea Wall/A Life, and he was announced to play Iago in Othello opposite Denzel Washington.
All sources
165 references cited across the entry
- 1InterviewAn Actor Pronounces My Last Name CorrectlyJake Gyllenhaal — October 13, 2014
- 2NLS Other Writings Say HowNational Library Service for the Blind and Physically Handicapped
- 3InterviewNobody Says Jake Gyllenhaal's Name CorrectlyJake Gyllenhaal — TBS — September 27, 2012
- 4Jake Gyllenhaal On The Toughest Role Of His Career: 'Sometimes I Took It Too Far'Dan Rookwood — January 11, 2018
- 5NewsJake's progressFred Schruers — October 30, 2005
- 6BookSveriges Ridderskap och Adels kalender 2010Riddarhuset — 2009
- 7NewsJake Gyllenhaal: My family valuesJanuary 1, 2011
- 8Stated on Finding Your Roots with Henry Louis Gates Jr., PBS, April 22, 2012. Retrieved July 29, 2017.
- 9'Bee' Spells Family D-y-s-f-u-n-c-t-i-o-n-a-lSusan Josephs — November 10, 2005
- 10Maggie Gyllenhaal: Acting for self-discoveryJanet Christie — June 22, 2014
- 11Jake Gyllenhaal: Going big – with a giant pigStephen Applebaum — June 22, 2017
- 12Maggie Gyllenhaal on her new role in BBC2 spy drama The Honourable WomanGerard Gilbert — July 2, 2014
- 13Maggie Gyllenhaal stars in SundanceTV's "The Honorable Woman"Naomi Pfefferman — July 23, 2014
- 14NewsJake Gyllenhaal: 'Pushing myself is part of my life'Tim Adams — April 24, 2016
- 15Jews in the News:Sarah Michelle Gellar, Julianne Margulies and Jake GyllenhaalTampa Jewish Community Center & Federation — October 3, 2013
- 17Jake Gyllenhaal Just Wants to Freak Himself OutThe Hollywood Reporter — June 5, 2024
- 18Gyllenhaal's Homeless Shelter Bar-MitzvahContact Music — November 6, 2005
- 19NewsJake Gyllenhaal shares views on sensitivity and masculinityRuben V. Nepales — December 14, 2016
- 20Interview with Jake GyllenhaalSteven Horn — May 28, 2004
- 21Jake Gyllenhaal - BiographyDominic Willis — 2006
- 22'October Sky' actress Natalie Canerday on Jake Gyllenhaal, Chris Cooper, film's legacy 15 years after debutKelly Kazek — July 23, 2014
- 23A breakout performance by Jake Gyllenhaal!Mark Halverson — 1998
- 24NewsJake's ProgressEimer, David — May 23, 2004
- 26News'Darko' takes a long, strange tripMike Snider — February 2, 2005
- 27Everything you were afraid to ask about 'Donnie Darko'Dan Kois — July 23, 2004
- 28Donnie Darko reviewGary Mairs
- 29NewsDirector, writer talk about 'The Good Girl'Anne Hubbell — CNN Entertainment — January 16, 2002
- 30BBC FilmsDavid Michael — October 21, 2002
- 31Slant Magazine reviewEd Gonzalez — 2001
- 32Bubble Boy (2001)August 24, 2001
- 33CNN.com - 'Bubble Boy' bursting with dumb humor - August 24, 2001Paul Clinton — CNN — August 24, 2001
- 34RottenTomatoes.com compilation of critical reviewsOctober 4, 2002
- 35Brad Silberling: The family that grieves together...Akin Ojumu — February 16, 2003
- 36NewsThis Is Our Youth reviewBillington, Michael — March 18, 2002
- 37NewsFast growing up to be famousDavid Gritten — April 13, 2002
- 39AlbemarleAlbemarle-London
- 40An Interview with Tobey MaguireJeff Otto — July 23, 2003
- 41Spiderman 2: An Interview with Sam RaimiWilson Morales — June 2004
- 42Jake Gyllenhaal: The New Batman?Stephen M. Silverman — September 3, 2003
- 43David S. Goyer Talks Batman, Iron Man, Comics and MoreJeff Otto — February 27, 2004
- 44BBC FilmJames Mottram — May 12, 2004
- 45Proof
- 46Jarhead
- 47News'Jarhead': A Platoon Full of Sand And GritStephen Hunter — November 4, 2005
- 48NewsThe one Jake: why Gyllenhaal spells successJohn Hiscock — December 12, 2005
- 49Somewhere over the rainbowGodfrey Cheshire — January 4, 2006
- 50NewsAng Lee wins Golden Lion at Venice Film FestivalSeptember 11, 2005
- 51The 78th Academy Awards 2006Academy of Motion Picture Arts and Sciences
- 52Film in 2006 BAFTA AwardsBritish Academy of Film and Television Arts
- 53Press releaseAcademy Invites 120 to MembershipAcademy of Motion Picture Arts and Sciences — July 6, 2006
- 54NewsJake Gyllenhaal Suffered with Unfriendly Ang LeeWenn — December 20, 2005
- 55Interview: Jake GyllenhaalCarlo Cavagna — December 2005
- 56News'Brokeback' Director Grabs Top AwardCBS News — January 26, 2005
- 57JakeBenoit Denizet-Lewis
- 59'Man on Wire' adds related shortBrian Cochrane — September 3, 2008
- 60Willems, Weston Woods win 2007 Carnegie Medal for "Knuffle Bunny"American Library Association — January 22, 2007
- 61NewsYouTube Extras: Jake as Effie, and a Musical "Scrubs"January 17, 2007
- 63Jake's ProgressJames Mottram — December 11, 2005
- 64NewsZodiac Production NotesParamount Pictures Press Kit — 2007
- 65Zodiac
- 66ZodiacPaul Byrnes — May 18, 2007
- 67New Line renders castDave McNary et al. — September 27, 2006
- 69Rendition - Gone Baby Gone - Terror's Advocate -- New York Magazine Movie ReviewDavid Edelstein — October 12, 2007
- 70NewsNatalie Portman to star in 'Brothers'Tatiana Siegel — October 2, 2007
- 72Jake Gyllenhaal Reconsiders2022-02-17
- 73Jake GyllenhaalHollywood Foreign Press Association
- 76End of Watch reviewSeptember 19, 2012
- 78Berlinale 2012: International JuryBerlin International Film Festival — December 19, 2011
- 79NewsIf There Is I Haven't Found It YetBrendan Lemon — Laura Pels Theatre, New York
- 80Jake Gyllenhaal & Denis Villeneuve Push Each Other Into Haunting, Bold New Territory For 'Enemy'Rodrigo Perez — September 6, 2013
- 81Magazine'Prisoners' ReviewPeter Travers — September 19, 2013
- 82Jake Gyllenhaal for dual 'An Enemy' rolesHugh Armitage — March 20, 2012
- 83NewsOn the Scent of Jake GyllenhaalCara Buckley — December 16, 2014
- 85Maggie Gyllenhaal on Brother Jake's Oscar Snub: "It's Not a Meritocracy"Hilary Lewis — January 25, 2015
- 86NewsAnd the Oscar nomination doesn't go to … 20 great performances snubbed by the AcademyLeigh Singer — January 23, 2024
- 87The 17 Biggest Oscar Nomination Snubs and SurprisesRamin Setoodeh — January 15, 2015
- 88Will Oscars nominate Jake Gyllenhaal for 'Nocturnal Animals' to make up for that shocking 'Nightcrawler' snub?Sam Eckmann — January 14, 2017
- 89The Jury of the 68th Cannes Film FestivalCannes Film Festival — April 21, 2015
- 90Jake Gyllenhaal, Sienna Miller and Guillermo del Toro Join Cannes Film Festival JuryGreg Gilman — April 21, 2015
- 91NewsJake Gyllenhaal to make Broadway debut in ConstellationsBen Beaumont-Thomas — June 13, 2014
- 92'Constellations,' With Jake Gyllenhaal and Ruth Wilson, Opens on BroadwayBen Brantley — January 13, 2015
- 93NewsSC Statehouse to Double as Capitol Hill; Gyllenhaal and Biel to StarGreg Hambrick — March 3, 2008
- 94For Southpaw director Antoine Fuqua, a different kind of boutSteven Zeitchik — July 24, 2015
- 95Southpaw is predictably absurd and unoriginal - reviewGeoffrey Macnab — July 23, 2015
- 96NewsEverest: how Jake Gyllenhaal got to grips with the world's highest mountainAndrew Pulver — September 2, 2015
- 97Everest
- 98NewsReview: In Demolition, It's Hammer Time for Jake GyllenhaalStephen Holden — April 7, 2016
- 99In 'Demolition,' a Finance Bro Finally Gets Hands-On and Feels SomethingBilge Ebiri — April 7, 2016
- 100Jake Gyllenhaal's Nocturnal Animals Lands Awards Season Release DateDave McNary — May 26, 2016
- 101Nocturnal Animals Trailer: Tom Ford Directs Jake Gyllenhaal & Amy AdamsZack Sharf — September 15, 2016
- 103NewsBafta nominations 2017: La La Land dances on but Arrival and Nocturnal Animals hot on its heelsCatherine Shoard — January 10, 2017
- 105Nocturnal Animals review: Story within a story becomes unsettling mind puzzleSandra Hall — November 6, 2016
- 106Review: Tom Ford's skillful meta-thriller 'Nocturnal Animals' revisits a broken marriageJustin Chang — November 17, 2016
- 107NewsSunday in the Park with George, with Jake Gyllenhaal, Adds 2 PerformancesMichael Paulson — July 14, 2016
- 108Sunday in the Park With George review – Gyllenhaal sings Sondheim superblyAlexis Soloski — October 27, 2016
- 109Review: 'Sunday in the Park With George,' a Living Painting to Make You SeeBen Brantley — February 23, 2017
- 110Jake Gyllenhaal on His Return to Broadway: Not So FastMichael Paulson — October 22, 2016
- 111NewsAdam Driver to Star in 'Burn This' on BroadwayGordon Cox — December 14, 2017
- 112Review: LifeEric Henderson — March 27, 2017
- 113Film reviews: Stronger, Human Flow, The Dinner, Brigsby Bear, MenasheGeoffrey Macnab — December 7, 2017
- 114Wildlife first look: Paul Dano's film is a picture of suburban sorrowElla Kemp — British Film Institute — September 26, 2018
- 115Hot Package: 'Nightcrawler's Dan Gilroy, Jake Gyllenhaal, Rene Russo ReteamMike Jr. Fleming — June 20, 2017
- 116NewsFilm Review: 'Velvet Buzzsaw'Peter Debruge — January 28, 2019
- 117NewsJake Gyllenhaal Eyed for Villain Role in 'Spider-Man: Homecoming' SequelJustin Kroll — May 21, 2018
- 118Biggest movies of 2019 – highest-grossing movies of the yearIan Sandwell — December 4, 2019
- 119'Sea Wall/A Life' Review: Jake Gyllenhaal Stars on BroadwayMarilyn Stasio — August 8, 2019
- 120Sea Wall / A LifeAmerican Theatre Wing and The Broadway League
- 121Strange World Teaser: Jake Gyllenhaal Voices Disney FilmSamantha Jorgeson — IndieWire — June 6, 2022
- 122Jake Gyllenhaal in 'The Guilty': Film Review TIFF 2021Michael Rechtshaffen — September 10, 2021
- 123Sonic the Hedgehog 2 to Lead Box Office Over Ambulance and MorbiusRebecca Rubin — April 6, 2022
- 124'Strange World': Release Date, Cast, Trailer, and Everything We Know So FarAidan Kelley — September 26, 2022
- 125NewsSTX Launches Sales On Guy Ritchie Action Thriller 'The Interpreter' With Jake Gyllenhaal As Stranded Soldier – AFM Hot PackageAndreas Wiseman — October 29, 2021
- 127Fresh Off 'Road House,' Amazon MGM Studios Signs First-Look Deal With Jake Gyllenhaal's Nine StoriesBrent Lang — April 2, 2024
- 128Jake Gyllenhaal's Nine Stories Signs First-Look Deal With Amazon MGM StudiosKristen Lopez — April 2, 2024
- 129NewsDenzel Washington and Jake Gyllenhaal to Lead Broadway 'Othello'Michael Paulson — March 6, 2024
- 130Maggie Gyllenhaal Talks Directing Brother Jake Gyllenhaal For The First Time In The Bride! & Early Feelings Of Envy In Her CareerNatalie Oganesyan — February 28, 2026
- 131People Magazine, "50 Most Beautiful People", April 28, 2006.
- 13210 Things to Love About JakeJune 9, 2006
- 133The 100 Sexiest Movie Stars: The MenWillow Green — October 7, 2013
- 134Sexiest Man of The Year 2018: Find out who has been crowned the winnerLeanne Bayley — December 18, 2017
- 135NewsJake Gyllenhaal: 'Aggression is a part of me'Nigel Farndale — October 21, 2007
- 136NewsJake GyllenhaalGlenn Sumi — December 15, 2005
- 137BAFTA winner Jake Gyllenhaal – Love and warStephen Applebaum — Netribution — January 27, 2006
- 138NewsJake Gyllenhaal on Nightcrawler: 'I'm a bit strange, you know?'Henry Barnes — October 30, 2014
- 139InterviewJake Gyllenhaal sees light in the darkness of NightcrawlerJake Gyllenhaal — September 10, 2014
- 141Meet Matilda Rose Ledger, the late Heath Ledger's only childSaul Lipchik — April 24, 2022
- 142NewsGyllenhaal, Dunst call it quitsKaren Thomas — July 20, 2004
- 143NewsReese Witherspoon & Jake Gyllenhaal Get CloseKatherine Thomson — April 5, 2007
- 144Reps Claim Jake and Reese Are Still TogetherUlrica Wihlborg et al. — November 29, 2009
- 145Taylor Swift & Jake Gyllenhaal Share a 'Friendly' Brunch in BrooklynSara Hammel — October 25, 2010
- 146Taylor Swift & Jake Gyllenhaal Break Up: SourceSara Hammel — January 4, 2011
- 149Who Is Jake Gyllenhaal’s Girlfriend? Everything to Know About Model Jeanne CadieuKaitlin Simpson — 2026-03-04
- 150Gyllenhaals forced to flee fire at lodgeDecember 29, 2006
- 151NewsStar of Donnie Darko visits ECAlison Pelleymounter — October 28, 2004
- 152JournalCelebrities rally votersKara Nichols — September 21, 2004
- 153NewsBeyoncé endorses Beto O'Rourke on Election Day: 'When we are truly united we are unstoppable'Sonia Rao — November 6, 2018
- 154Celebrities Speak Out for Civil Liberties in New ACLU Advertising CampaignAmerican Civil Liberties Union — September 15, 2003
- 155Open All Night: ACLU Freedom ConcertDennis Van Tine et al. — October 4, 2005
- 156NewsJake Gyllenhaal is the Honorary Chair of the New Eyes For The Needy Advisory BoardNovember 21, 2012
- 157Fox, Jake Gyllenhaal Join Stand Up To CancerJuly 13, 2010
- 158MagazineWhy the Producer of 'The Hangover Part III' Spends So Much Time in PrisonMichael Mechanic — May 23, 2013
- 159Jake Gyllenhaal, Anthony Edwards Offer Words of Support for Military VetsHilary Lewis — October 2, 2014
- 160NewsJake Gyllenhaal, Steve Buscemi and More Take Part in 9/11 FundraiserSara Kitnick — September 12, 2017
- 161The Day After Tomorrow – Jake Gyllenhaal Q&AJack Foley — 2003
- 1622004: The year of Jake GyllenhaalCarolann Curry — May 27, 2004
- 163NewsIce CrusadeJuliet Eilperin — April 26, 2005
- 164Arctic WisdomSpectral Productions Inc. — April 21, 2005
- 165NewsJake Gyllenhaal: 'Women? They're superior to men'Sophie Heawood — September 26, 2021