It would have been the rare critic who could have predicted Owen Wilson would be an Oscar nominee just six years after his debut in the 1996 film Bottle Rocket. But in fact, in 2002, the blondest of the Wilson brothers was nominated alongside his Bottle Rocket co-writer and longtime collaborator, Wes Anderson, for their original screenplay for The Royal Tenenbaums.

Together the duo has worked on five features including 1998’s Rushmore and 2004’s The Life Aquatic with Steve Zissou, but it is for his work with Ben Stiller and other members of the so-called “Frat Pack” that Wilson is best known. Whether he’s trying to play it straight in Meet the Parents or hamming it up in the big-screen adaptation of Starsky & Hutch, Wilson’s on-screen alter egos have provided audiences with years of laughter, tears, heartache and even more laughter.

As Drillbit Taylor makes a splash at the box office this weekend, MM takes a look at Wilson’s on-screen personas past and present.

Wilson was unusually convincing as Hansel, a scooter-riding, feather boa-wearing male model in 2001’s Zoolander. This role would mark the fourth on-screen pairing for the actor and his co-star Stiller. To date they’ve made eight movie appearances together, with Night at the Museum 2: Escape from the Smithsonian scheduled for a 2009 release.
Shanghai Knights
shanghai knights
In the year 2000, Wilson took on the role of outlaw Roy O’Bannon in the comedy Shanghai Noon. The odd dynamic between Wilson and co-star Jackie Chan proved comedy gold (pulling in a cool $70 million) that led to the 2003 sequel, Shanghai Knights. This time around the men didn’t fair so well critically, although Wilson did stand out for Desson Thomson of The Washington Post who explained, “Wilson has his surfer-dude moments of humor, but he’s doing his best with creatively dead material.”
The Wendell Baker Story
Wendell Baker Story

Written, co-directed and starring his brother Luke (the other co-director was older brother Andrew), this 2005 independent dramedy put Owen in costume as the head nurse at a retirement home.
Wedding Crashers
wedding crashers
Starring opposite Vince Vaughn, Wilson played a divorce lawyer who spent his free time crashing weddings. Carefree and bold at first, Wilson’s John Beckwith turned serious and dedicated after he crossed paths with an intriguing romantic prospect. The raunchy adult comedy became one of 2005’s biggest summer blockbusters, taking in over $280 million at the box office.
The Darjeeling Limited
Darjeeling Limited
In his latest collaboration with Anderson, Wilson plays brother to Adrien Brody and his Rushmore star Jason Schwartzman, the three of whom embark on a spiritual and emotional journey across India by way of The Darjeeling Limited.
Drillbit Taylor
It’s unclear how many parents would want Owen Wilson’s Drillbit Taylor as their son’s mentor, but odds are, every teenage boy would jump at the chance to be his apprentice. In the comedy, out in theaters now, three bullied teens hire Taylor as their bodyguard—and learn a little more than they bargained for along the way.