8 Milestones in the Evolution of Owen Wilson

Zoolander (2001)

Speaking of Stiller, Wilson's then-fifth collaboration with the star (following The Cable Guy, Permanent Midnight, TV's never-seen Heat Vision and Jack and Meet the Parents), found him playing yet another straight man. Sorta. Not really. Hansel was Derek Zoolander's up-and-coming competition and foil, who ended up helping his industry foe stop a political assassination...after this legendary walk-off scene judged by David Bowie.

The Royal Tenenbaums (2001)

In Wilson's second feature film with Wes Anderson, the star assumed the supporting role of Eli Cash, an intelligent yet off-the-wall neighbor of the Tenenbaums who always fantasized about being part of the family. Even though he was Richie's (Luke Wilson) best friend, he carried on an affair with Margot (Gwyneth Paltrow) and allowed his literary celebrity to lead him down a rabbit hole of drug-addled antics. Tenenbaums earned Wilson his first -- and only -- Academy Award nomination for Best Original Screenplay.

Wedding Crashers (2005)

Wilson reunited with his Shanghai Knights director David Dobkin in 2005 to star in this high-spirited film with Vince Vaughn, which went on to earn over $200 million and launched him onto the A-list. Wedding Crashers was Wilson's first real opportunity at being a "Romantic Comedy Lead," a title he would accept many times in the five years since....

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