His career progressed with starring roles in the thriller Zodiac (2007), the romantic comedy Love & Other Drugs (2010), and the science fiction film Source Code (2011).

After playing a supporting role in the drama Wildlife (2018), Gyllenhaal starred in action or thriller projects, including the films The Guilty (2021), Ambulance (2022) and Road House (2024), as well as the series Presumed Innocent (2024).

[16][17] 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.

[6] 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.

[25] Directed by Richard Kelly, the film is set in 1988 and stars Gyllenhaal as a troubled teenager who experiences visions of a 6-foot (1.8 m) tall 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.

[33] Following Bubble Boy, Gyllenhaal starred opposite Dustin Hoffman, Susan Sarandon and Ellen Pompeo in 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,[34] is loosely based on writer-director Brad Silberling's personal experiences following the murder of his girlfriend, Rebecca Schaeffer.

"[37] The play ran for eight weeks in London's West End; Gyllenhaal received favorable reviews and an Evening Standard Theatre Award in the Outstanding Newcomer category.

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".

[46] 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.

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.

[57]Gyllenhaal narrated the 2005 short animated film The Man Who Walked Between the Towers,[58] based on Mordicai Gerstein's book of the same name about Philippe Petit's famous stunt.

[63] 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".

[66] Two years later, he co-starred with Tobey Maguire and Natalie Portman in Jim Sheridan's Brothers, a 2009 remake of Susanne Bier's Danish film of the same name.

[67] It was met with mixed reviews and moderate box office returns, but Anthony Quinn of The Independent thought Gyllenhaal and Maguire gave "honest performances".

[69] The following year, Gyllenhaal played the lead role in Prince of Persia: The Sands of Time, an adaptation of the video game of the same name, produced by Jerry Bruckheimer and released by Disney.

[72] 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's Andrew O'Hehir stating that the film was "at least the best cop movie since James Gray's We Own the Night, and very likely since Antoine Fuqua's memorable Training Day (which, not coincidentally, was written by Ayer)".

[73][74] 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.

[84] 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.

[90] 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.

[95] The Sydney Morning Herald's 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.

[96][97] 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.

[103] He also had a supporting role in the action-adventure film Okja and starred in the drama Stronger, based on Boston Marathon bombing survivor Jeff Bauman.

[94] Gyllenhaal reunited with Nightcrawler director Dan Gilroy in the thriller film Velvet Buzzsaw, in which he plays art critic Mort Vandewalt.

[109] He appeared alongside Tom Sturridge in Sea Wall/A Life, a double bill of monologues by Nick Payne and Simon Stephens, at the Hudson Theatre on Broadway in 2019.

[118][119] 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.

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.

[159][160] Gyllenhaal's most acclaimed 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).