Born into a Hollywood family with a director father, screenwriter mother and scene-stealing sister, Jake Gyllenhaal was pretty much destined to give Tinseltown a try. (He even got driving lessons from family pal Paul Newman.) Thanks to his rugged good looks, sensitive baby blues and a boatload of talent, he’s probably here to stay. He got his first taste of the big screen at 11 when he played Billy Crystal’s son in "City Slickers." The former lifeguard and temp Columbia undergrad delivered early nuanced performances in "October Sky" (1999), "Donnie Darko" (2001), "The Good Girl" and "Moonlight Mile" (2002) In 2005, he became a bona fide above-the-title star as a marine in "Jarhead" and a cowboy who fell for Heath Ledger (whose kid is Gyllenhaal’s godchild) in "Brokeback Mountain." The latter even earned him an Oscar nod. He went wild with Bear Grylls for a TV episode and when he played a L.A. cop in "End Of Watch" (2012). Currently single, the bearded babe stepped out with Taylor Swift briefly in 2010 and spent two years as Reese Witherspoon’s rebound after they met on the set of "Rendition" in 2007. Prior to those pairings, he shared promise rings, adopted a German shepherd and cohabited with Kirsten Dunst.
Jake Gyllenhaal Search Results
Cannes StyleTake a look back at the all-time most memorable fashions of the Cannes Film Festival.
2014 Met GalaSee your favorite stars at The Metropolitan Museum of Art's Costume Institute Benefit Gala.
Week In PhotosKim Kardashian was spotted out and about in Calabasas, Calif., plus more of your favorite stars this week in photos.
Courting KatieKatie Holmes is back on the market. Who should she date next? You decide!
Epic LoveTake a look back at John and Yoko, plus more of pop culture's most epic romances.
Famous GodparentsFind out the surprising famous godparents of Nicole Richie, Gwyneth Paltrow and more of your favorite stars.
Sexy SoldiersCelebrate Memorial Day with pop culture's hottest servicemen and women.
Sexy CowboysCheck out Kevin Costner and more of the top 25 hottest pop culture cowboys.
Cowboy ClubFrom Armie Hammer as the Lone Ranger to Heath Ledger in "Brokeback Mountain," these are our favorite pop culture cowboys.
Baby BluesGet your fix of hunky stars with dreamy baby blue eyes!