12:57 AM EDT 07/26/2016

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Jake Gyllenhaal

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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Credit: Clint Spaulding/PMC/Sipa
Naomi Watts on Her Demolition Costar Jake Gyllenhaal's Parenting Instincts: 'Yes, He Should Be a Dad!'

Naomi Watts on Her Demolition Costar Jake Gyllenhaal's Parenting Instincts: 'Yes, He Should Be a Dad!'

Originally posted 03/23/2016 05:15PM

Jake Gyllenhaal may not have children of his own, but his many fatherly roles have sure prepared him for the day he does.

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Credit: Getty
FROM EW: How Jake Gyllenhaal Bombed His Lord of the Rings Audition

FROM EW: How Jake Gyllenhaal Bombed His Lord of the Rings Audition

Originally posted 03/22/2016 11:45AM

Gyllenhaal said the first part was wordless and he didn't put a lot of effort into it

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Credit: Getty
Jake Gyllenhaal Brightens St. Patrick's Day for an Injured Boston Hockey Player

Jake Gyllenhaal Brightens St. Patrick's Day for an Injured Boston Hockey Player

Originally posted 03/18/2016 07:20PM

Jake Gyllenhaal's surprise St. Patrick's Day visit at a Boston hospital made several patients feel like they had the luck of the Irish.

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Credit: Getty
Jake Gyllenhaal Spotted 'Catching Up and Relaxing' with Friends in Boston Before Filming Marathon Bombing Movie

Jake Gyllenhaal Spotted 'Catching Up and Relaxing' with Friends in Boston Before Filming Marathon Bombing Movie

Originally posted 03/10/2016 10:55PM

Jake Gyllenhaal knows how to catch up with old friends in style.

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FROM EW: Jake Gyllenhaal Wields a Sledgehammer in New Demolition Trailer

FROM EW: Jake Gyllenhaal Wields a Sledgehammer in New Demolition Trailer

Originally posted 02/04/2016 05:40PM

The new trailer for Jean-Marc Valleeā€™s Demolition with Jake Gyllenhaal

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