The 10 Best Owen Wilson Performances

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Today, November 18, Owen Wilson celebrates his 44th birthday. Raised in Dallas, Texas, Wilson was expelled from the private high school he attended with his brother, Luke. He then attended military school in New Mexico and later, the University of Texas in Austin. There he met aspiring filmmaker Wes Anderson, and the rest is history. Since breaking through with his role in Bottle Rocket, Wilson quickly became one the most popular comedic actors in Hollywood. He never got too big to work with his original collaborator, however, and the two will team up once again in The Grand Budapest Hotel, currently in production.

In honor of Wilson’s birthday, we’ve compiled our list of his 10 greatest roles. Take a look below and let us know what you think.

10. Lieutenant Chris Burnett in Behind Enemy Lines
Owen Wilson, action star? Yes indeed. In 2001’s underrated Behind Enemy Lines, Wilson plays a disgruntled Navy pilot who ends up, you guessed it, behind enemy lines after his plane is shot down during a routine reconnaissance run. With the help of an authority-bucking Gene Hackman, Wilson is eventually rescued before a Bosnian guerrilla army can catch him.

9. Francis Whitman in The Darjeeling Limited
After surviving a near fatal accident, Wilson’s character, Francis Whitman, decides to organzie a trip through India with his brothers with the ultimate goal to reconnect with their mother (Anjelica Huston). At first, his control over the trip is obsessive—he passes out laminated daily itineraries and orders food for his brothers— but eventually he learns to loosen up, let the journey play itself out and, as a result, he forms a deeper bond with his brothers.

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8. Randolph Dupree in You, Me and Dupree
You, Me and Dupree sees Wilson with his hair at its longest and his acting style at its most laid back. Despite his aloofness, Dupree is one of Wilson’s wildest, most out-there characters, inadvertently reeking havoc on the new marriage of his best friend Carl (Matt Dillon) and Molly (Kate Hudson) after “temporarily” moving into their house.

7. Ned Plimpton in The Life Aquatic with Steve Zissou
In The Life Aquatic, Wilson plays Ned Plimpton, an innocent, unassuming pilot for Air Kentucky who is the suspected son of the relatively brusque Steve Zissou (Bill Murray). Despite their disparate backgrounds, Ned tags along with his supposed father’s mission to kill a tigershark, setting the stage for a boat ride full of classic Wes Anderson familial dysfunction.

6. Hansel in Zoolander
Zoolander was a landmark comedy in 2001, and Wilson was front and center as Hasel, Derek Zoolander’s modeling nemesis who cares more about what bark is made out of and idolizing Sting (not for his music, but for the fact the he’s out there doing it) than his rivalry with Ben Stiller’s Zoolander. Eventually, the two supermodels team up to bring down Mugatu (Will Ferrell), after he brainwashes Zoolander with the Frankie Goes to Hollywood song “Relax.”

5. John Beckwith in Wedding Crashers
Along with Old School, Wedding Crashers was one of the most quintessential “frat pack” movies of the ‘00s. Wilson played the more sensitive crasher opposite the gregarious Vince Vaughn, who suffered at the hands of the psychotic Isla Fisher so that Wilson could pursue his dream girl, Rachel McAdams. Despite the best efforts of Christopher Walken and Bradley Cooper, however, both crashers end up getting their girls.

4. Kevin Rawley in Meet the Parents
Wilson only played a minor role in Meet the Parents and its sequels, but his character of the all-too-perfect Kevin Rawley, Pam’s ex-boyfriend, is one of the film’s most hilarious roles, especially when pitted against the bumbling Ben Stiller. Plus, it only took him 70 hours to carve a wedding altar by hand from a single piece of wood.

3. Gil Pender in Midnight in Paris
Gil Pender, a Hollywood screenwriter going through a mid-life crisis, is a role seemingly tailor-made for Wilson to play—wide-eyed, in over his head, dressed in khaki and romantically involved with Rachel McAdams. Although it’s hard to hold the wide-eyed and in-over-his-head parts against him; he did discover a time portal to the Jazz Age.

2. Eli Cash in The Royal Tenenbaums
Although he co-wrote it, Wilson did not appear in Wes Anderson’s second film, Rushmore. The duo reunited a few years later, however, for The Royal Tenenbaums, with Wilson again co-writing and appearing as Eli Cash, the drug-addled, Cormac McCarthy-style novelist and wannabe Tenenbaum who has an affair with Gwenthy Paltrow’s character, Margot. He also helps bring the discordant Tenenbaums together again when he crashes Etheline’s wedding (literally) by running his sports car into the side of the building while wearing face paint. Did we mention he was drug-addled?

1. Dignan in Bottle Rocket
Wilson’s first role was also his best. After meeting Wes Anderson at the University of Texas, the two teamed up to write Bottle Rocket, a cult classic about two outcast friends trying to distance themselves from their roots. Starring opposite his real-life brother, Luke, Owen inhabited all of Dignan’s insecurities en route to masterminding an ill-fated heist of a cold-storage facility.