8 Milestones in the Evolution of Owen Wilson

In James L. Brooks's new romantic comedy How Do You Know, Owen Wilson co-stars as a loopy, commitment-phobic major league pitcher who romances Reese Witherspoon's character (to the best of his ability) during a low point in her career. How did Wilson get to a point in his career where he is acting opposite Oscar winners (Witherspoon, Jack Nicholson) in an Academy Award-decorated scribe's script? Movieline charts the eight roles that lead Owen Wilson to this point.

Bottle Rocket (1996)

Based on the 1994 short film of the same name, this comedy marked the feature film debut of Wilson (who co-wrote the screenplay), along with brothers Luke, Andrew and longtime friend Wes Anderson, who directed and co-wrote this commercial flop. Wilson's role in Bottle Rocket was the first in a line of aimless dreamer characters with elaborate-yet-eccentric schemes. Here, he played Dignan, a young Texan who breaks a friend (Luke Wilson) out of a mental hospital and proceeds to lead him through a 75-year plan which includes various heists, an eccentric mentor (James Caan) and a Spanish-speaking maid (Lumi Cavazos).

Shanghai Noon (2000)

It could be argued that Owen Wilson has never been less funny than when he took his first paycheck starring role opposite Jackie Chan in this Wild West action flick. As Roy O'Bannon, a gun-toting, wise-cracking, bar brawling outlaw, Wilson helps his unlikely martial artist partner-in-crime track down a princess when they are not chatting and swilling shots in side-by-side bathtubs, as they do below. If anything Noon was significant because it was the first time Wilson was a co-star and not a member of an ensemble (see: Armageddon and Anaconda).

Meet the Parents (2000)

In one of his rare "straight man" roles, Owen Wilson played Pam's ex-fiance, a successful businessman, adventurer and expert carpenter, who posed a threat to Pam's new fiance, Gaylord (Ben Stiller). It was Wilson's third film with Stiller -- the pair starred in Permanent Midnight and also appeared separately in The Cable Guy -- and he has appeared with him six times since (including the Parents sequels).

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