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).
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....
You, Me and Dupree (2006)
...though not in You, Me and Dupree. In the aimless comedy, Wilson played the wacky part of a romantic comedy "love triangle," as the loner house guest who comes between his best friend and his friend's new wife. It didn't really work. Wilson would go back to regular rom-com grounds with the $140 million grossing Marley & Me, and now How Do You Know.
Darjeeling Limited (2007)
Just two months after the actor's alleged suicide attempt, this 2007 Wes Anderson film (which, for a change of pace, was not co-written by Wilson) was released. Like in Bottle Rocket, Wilson straddled the line between conniving and dippy, this time herding his two brothers (Adrien Brody, Jason Schwartzman) on a soul-searching trip through India to reconnect with their mother (Angelica Huston). Eerily, Wilson's character spent most of the film in facial bandages, which when removed during a later scene, revealed bruising from an accident that may or may not have been a suicide attempt.