“Bubble Boy” (2001)
One of Gyllenhaal’s earliest film credits is as Jimmy Livingston — a boy without an immune system who lives in a bubble — in “Bubble Boy”
“Donnie Darko” (2001)
Perhaps one of Gyllenhaal’s most notable roles, the actor stars as the titular character in this cult classic about a troubled teenager with disturbing visions
“The Good Girl” (2002)
In “The Good Girl,” Gyllenhaal plays Holden, the love interest of Jennifer Aniston‘s character Justine Last. The two start an affair while working together at a local department store
“Moonlight Mile” (2003)
After Joe Nast’s (Gyllenhaal) fiancée Diana Floss was murdered in a shooting, he opts to stay with her parents and mourn her loss together
“The Day After Tomorrow” (2004)
In this sci-fi flick, Gyllenhaal plays Sam Hall — a baby-faced teenager visiting Manhattan when disastrous weather strikes
“Brokeback Mountain” (2005)
Gyllenhaal plays Heath Ledger‘s lover Jack Twist in one of the most innovative films of all time. The two gay cowboys earned several Academy Awards nods.
“Jarhead” (2005)
Gyllenhaal stars as real-life United States Marine Anthony Swofford who is deployed to fight in the Gulf War
“Zodiac” (2007)
In “Zodiac,” Gyllenhaal’s character Robert Graysmith is fascinated by a notorious serial killer in San Francisco. He later goes on to pen a book about the self-named Zodiac killer, though the murders remain unsolved
“Brothers” (2009)
Gyllenhaal stars opposite Tobey Maguire in “Brothers,” a story about a Marine with intense post-traumatic stress disorder
“Prince of Persia: The Sands of Time” (2010)
The actor stars as Dastan in this adventure action fantasy film based on the video game, as Gyllenhaal proves he is capable of taking on a macho persona in an action flick
“Love & Other Drugs” (2010)
In “Love & Other Drugs,” he plays Jamie Randall — a successful Viagra salesman and Anne Hathaway‘s love interest
“Prisoners” (2013)
Gyllenhaal stars as Detective Loki, a somber character who is tasked with the safe return of two girls who go missing
“Nightcrawler” (2014)
Gyllenhaal portrays Louis “Lou” Bloom in “Nightcrawler” — a freelance cameraman who shoots crime scenes. Oftentimes, he tampers with evidence for the sake of a better, more profitable shot
“Enemy” (2014)
Gyllenhaal is his own co-star in “Enemy,” a psychological thriller about one identical twin who stalks the other
“Southpaw” (2015)
The actor plays down-and-out boxer Billy Hope in “Southpaw.” The fighter undergoes an inspiring comeback story after the death of his wife (Rachel McAdams)
“Demolition” (2016)
The actor plays a young finance exec who goes into a tailspin while mourning the sudden death of his wife.
“Nocturnal Animals” (2014)
The actor played dual roles in Tom Ford’s acclaimed thriller, as both struggling novelist (and ex-husband of Amy Adams’ gallery owner) as well as the protagonist of that writer’s creepy novel.
“Sunday in the Park With George” (2017)
Gyllenhaal starred with Annaleigh Ashford in a Broadway revival of the Stephen Sondheim musical as 19th-century French artist Georges Seurat.
“Life” (2017)
Gyllenhaal stars opposite Ryan Reynolds and Rebecca Ferguson as astronauts who discover life on Mars — and it seems less than friendly to human visitors.
