02:47 PM EDT 09/20/2016

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Jake Gyllenhaal

Jake Gyllenhaal Remembers Donnie Darko: 'This Feels Like My High School Experience'

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.

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Credit: Rich Fury/Invision/AP
Playing the Name Game with Jake Gyllenhaal

Playing the Name Game with Jake Gyllenhaal

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

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Filed Under: Jake Gyllenhaal

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.

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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.

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Jake Gyllenhaal Loved Leaving Vanity Behind for Demolition

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.

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Jake Gyllenhaal on Ex Reese Witherspoon: 'One of the Smartest, Strongest People I've Ever Met'

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?

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Jess Cagle

Jake Gyllenhaal Admits He Had a Crush on Jennifer Aniston 'For Years'

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.

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Jake Gyllenhaal on Heath Ledger's Death: 'It Affected Me in Ways I Can't Put Into Words'

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.

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Credit: Getty
Jake Gyllenhaal Training Heavily for Boston Marathon Bombing Movie Stronger

Bodywatch

Jake Gyllenhaal Training Heavily for Boston Marathon Bombing Movie Stronger

Originally posted 04/01/2016 03:35PM

Jake Gyllenhaal is serious about his workouts.

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WATCH: Jake Gyllenhaal and Naomi Watts Form an Unlikely Bond in Demolition Clip

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.

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