Jake Gyllenhaal Suits Up to Start Filming in Canada Siblings Maggie and Jake Gyllenhaal Bond Over a NYC Stroll Jake Gyllenhaal Joins Some Funny, Famous Friends For a Good Cause Jake Gyllenhaal Rocks a Big Beard and Eyes a New Gig Look Back at Highlights From the Independent Spirit Awards Jake Gyllenhaal Wraps Up the Berlin Film Festival With His Fellow Judges All the Berlin Film Festival Pictures With Rob, Angelina, and More Jake Gyllenhaal Spends Valentine's Day With Iron Lady Meryl Streep Jake Gyllenhaal Suits Up and Begins Judging the Berlin Film Festival Jake Gyllenhaal Gets to Know His Fellow Berlin International Film Festival Jurors Jake Gyllenhaal Gets a Warm Welcome in Germany Jake Breaks Out His Spring Staples For a Lunch Jake Gyllenhaal Stocks Up on Juice While Taylor Swift Alludes to Their Breakup See All the Golden Globes Pictures — Red Carpet, Show, Parties, and More! Celebrate Jake Gyllenhaal's Birthday With His Sweet, Sexy, and Shirtless Moments Through The Years! Jake Gyllenhaal Plays Doting Uncle to Little Ramona A Bushy Bearded Jake Gyllenhaal Supports a Friend's Film A Scruffy Jake Gyllenhaal Chats Up His Friend and Former Costar Michelle Williams at Her Premiere See Brad, Javier, Reese, Oprah, and More in a Look Back at the Toronto International Film Festival! Jake Gyllenhaal Leaves His Ladies to Take a Hike With Atticus Jake Gyllenhaal and Anna Kendrick Spotted Cuddling Close! Jake Gyllenhaal and Rashida Jones Do Lunch in LA With Atticus Jake Gyllenhaal Enjoys a Very Hot Day Off in LA Jake Gyllenhaal Is Packing Heat and Keeping His Guns Covered on Set