12:57 AM EDT 07/26/2016
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.
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.
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
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.
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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