2004

Jake Gyllenhaal

June 14

Settling In

Dunst and Gyllenhaal share the actress's $1.7 million Los Angeles home and wear gold promise bands (hers on a chain around her neck). "I am really happy and in love," she tells PEOPLE.

July 20

Moving On...

Dunst's rep announces that her client and Gyllenhaal have split up. Declining to provide details or dates, the rep says, "Kirsten and Jake remain the best of friends. . . They are still very close." A few weeks later, the former couple are spotted on a lunch date in L.A. Dunst's rep denies a revived romance but the pair are spotted together again and again.

2005

Jake Gyllenhaal

November 04

New Role, New Look

Gyllenhaal plays a marine in the Gulf War drama Jarhead, costarring with Jamie Foxx and Peter Sarsgaard (his sister's love interest). As for the military "do," "They buzz it every other day," he tells PEOPLE. "It's a science." Would he shave it again after the film? "Without a doubt," he says. "I felt really badass! I felt strong, present and alive. It takes the sense of vanity away."

Jake Gyllenhaal

December 09

'I Wish I Knew How to Quit You'

Brokeback Mountain, a movie about two men who fall in love during a sheepherding expedition, opens to critical acclaim. Gyllenhaal plays flashy rodeo cowboy Jack Twist opposite Heath Ledger's quiet, conflicted Ennis Del Mar. "I really did approach it like I would any love story," Gyllenhaal tells Entertainment Weekly. Both actors earn Oscar nominations for their heart-felt performances.

2006

December 28

Real Help

The leading man lends a real hand when the San Francisco lodge where he and his family are vacationing for the holidays catches fire. "Jake was helping me pull things out of the fire," Daniel DeLong, a chef and co-owner of the historic lodge, told the Marin Independent Journal. No one was injured.

2007

Jake Gyllenhaal

March 02

Gyllenhaal's Zodiac

Suspense thriller Zodiac, starring Gyllenhaal, Robert Downey Jr. and Mark Ruffalo, opens at No. 2. New York Times film critic Manohla Dargis dubs the stars a "trio of beauties" who are "all at the top of their performance game." The true-crime film explores the notorious Zodiac serial killer that stalked the Bay area and is directed by David Fincher (Se7en). Gyllenhaal plays cartoonist-turned-writer Robert Graysmith, who obsessively corresponds with the possibly still-at-large, unidentified murderer.

Jake Gyllenhaal

March

More than Costars

Gyllenhaal quietly spends time with Rendition costar Reese Witherspoon, who split with husband Ryan Phillippe five months earlier. In 2009, after spending two years together, the couple calls it quits. "Jake would marry her tomorrow," a source tells PEOPLE. "But Reese doesn't want to go there yet, even though he would like to."

2010

Jake Gyllenhaal

May 28

Superhero Shape

Gyllenhaal gets ripped for The Prince of Persia, where he plays a street urchin-turned-hero. "It was so hard," he sarcastically tells PEOPLE. "Being an actor is so hard. Being in shape is so hard, too, and being paid to get into shape is even harder – and you can quote me on all of those."

Jake Gyllenhaal

October

Jake's Country Cutie

After attending Saturday Night Live together, Gyllenhaal, 29, and Taylor Swift, 20, are spotted having brunch in Brooklyn the next day. "They're cute together," a source close to the actor tells PEOPLE, before the pair hit the singer's hometown of Nashville during their brief romance.

Jake Gyllenhaal

November

Nude Awakening

Gyllenhaal and Love and Other Drugs costar Anne Hathaway strip down for EW, and dish on their latest collaboration. "Our first interaction as actors in a scene in Brokeback, the rhythm was just on," Gyllenhaal says of his chemistry with his two-time costar. "You know the actors that you're just going to go somewhere with."

Photo Credits

BIOGRAPHY (top to bottom): GINSBURG-VIBBERT; Francois Duhamel/Universal; Universal Pictures; Everett Collection; Bauer Griffin; Andrew Cooper/Disney; Swarbrick/INF

Edited by Julia Wang

Jake Gyllenhaal

Celebrity Central / Top 25 Celebs

 

From Our Partners



Sign up for our daily newsletter and other special offers.
    Choose your newsletters
Thank you for signing up! Your request may take up to one week to be processed.
    see all newsletters