02:47 PM EDT 09/20/2016
Originally posted 04/11/2016 09:00AM
Jake Gyllenhaal has played his share of intense characters – a star-crossed cowboy in Brokeback Mountain, a streetwise LAPD officer in End of Watch, a cold-blooded crime-scene chronicler in Nightcrawler – but none was more fraught, or rewarding, than his breakout role in Donnie Darko.
Originally posted 04/08/2016 10:40AM
During an episode of The Jess Cagle Interview, the actor plays name association with some of his favorite costars from over the years
Spoiler Alert! Jake Gyllenhaal Reveals He Has No Idea How His Favorite Childhood Movie Ends – Here's Why
Originally posted 04/08/2016 09:00AM
Be careful with spoilers if you're ever around Jake Gyllenhaal.
Jake Gyllenhaal Looks Back on His First Role in City Slickers: 'It Was an Interesting, Very Complicated Time'
Originally posted 04/07/2016 11:00AM
Long before Jake Gyllenhaal hit it big as a troubled teen in Donnie Darko or a cowboy romancing Heath Ledger in Brokeback Mountain, he played a bashful young boy in 1991's City Slickers, so embarrassed by his father's humdrum ad job that he introduced him as a submarine commander to his class.
Originally posted 04/07/2016 09:00AM
In Demolition, Jake Gyllenhaal stars as a man who, after losing his wife in a car crash, decides to impulsively take a sledgehammer to his house – and his entire life. But when Gyllenhaal sat down for the latest edition of The Jess Cagle Interview, he revealed that his character, Davis Mitchell, wasn't the only spontaneous one on set, as director Jean-Marc Vallée brought a lot of that same improvisation to his directing style.
Originally posted 04/06/2016 03:00PM
Jake Gyllenhaal and Reese Witherspoon never appeared onscreen together in the 2007 film Rendition, but they met on the set of that political thriller and later began dating, a relationship that lasted until their split in 2009. So what's the first thing that comes to Gyllenhaal's mind when he thinks of Witherspoon now?
Originally posted 04/06/2016 11:00AM
Jake Gyllenhaal has starred with some of Hollywood's biggest actresses throughout his career – everyone from Anne Hathaway to Rene Russo to Rachel McAdams to Natalie Portman to Reese Witherspoon. But it was Jennifer Aniston, Gyllenhaal's costar in The Good Girl, who left the actor almost speechless.
Originally posted 04/06/2016 09:00AM
Heath Ledger's death in 2008 sent shockwaves through many inside the Hollywood community, including Jake Gyllenhaal. The actor starred opposite Ledger in the 2005 film Brokeback Mountain, and says Ledger's death impacted both his personal and professional life.
Originally posted 04/01/2016 03:35PM
Jake Gyllenhaal is serious about his workouts.
Originally posted 03/24/2016 12:30PM
When Jake Gyllenhaal's life starts to unravel in Demolition, an unlikely connection with Naomi Watts helps him put it back together.
The most buzzed about stars this minute!
Treat Yourself! 4 Preview Issues
More On PEOPLE.com
Got a News Tip?
Send it to our People.com editors!