8 Milestones in the Evolution of Jake Gyllenhaal

The Day After Tomorrow (2004)

And here's where the action begins. After starring opposite Jennifer Aniston in 2002's The Good Girl -- and opposite Dustin Hoffman, Susan Sarandon and Ellen Pompeo in Moonlight Mile -- Gyllenhaal took the lead role in The Day After Tomorrow, one of Roland Emmerich's 20 or so efforts to destroy the world. The film grossed $544 million worldwide, after which perhaps Gyllenhaal realized that his financial destiny lay not in cult indie classics or terrible comedies.

Brokeback Mountain (2005)

Six years later (really?), it's kind of amazing the amount of controversy that this movie produced. Especially when you realize that the most controversial thing about Brokeback Mountain today is that Randy Quaid somehow played a major role. Regardless, Gyllenhaal built on what audiences already witnessed with his performance in The Good Girl. Here he played Jack Twist, a rancher who falls in love with fellow rancher, Ennis Del Mar (Heath Ledger). Gyllenhaal would receive his first and -- to date -- only Oscar nomination. (On a related note, Brokeback Mountain wins the YouTube award for "hardly any clips, but has the most homemade montages set to popular love songs"... so, here's the trailer.)

Zodiac (2007)

Gyllenhaal portrayed San Francisco Chronicle cartoonist Robert Graysmith in this underrated thriller from David Fincher. Just don't expect to see Gyllenhall and Fincher ever work together again, after Gyllenhaal's now-somewhat-infamous quote about Fincher: "You get a take, 5 takes, 10 takes. Some places, 90 takes. But there is a stopping point. There's a point at which you go, 'That's what we have to work with.' But we would reshoot things. So there came a point where I would say, well, what do I do? Where's the risk?" Regardless, this is the type of role that Gyllenhaal is made for.

Prince of Persia: The Sands of Time (2010)

When one thinks "big budget blockbuster, based on a video game, set during the Persian Empire," Gyllenhaal's name is not exactly the first one that comes to mind. Yet, here it is! I can actually picture Gyllenhaal sitting at a table, being asked how he wants to proceed into action films. "Do you want to take baby-steps, Jake?" Gyllenhaal, with that wry smile, looks up and stoically announces, "All in" -- then he pushes every last chip in front of him to the middle of the table. (There are chips in this fantasy; deal with it.)

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