While Wilson found some initial success as a film actor after his turn as Dignan in Bottle Rocket, he also remained a key creative collaborator in Wes Anderson's next two directorial efforts. Rushmore was the two writers' second script collaboration. Although Wilson didn't appear in the film, he and Anderson acknowledged on the Criterion Collection DVD audio commentary that Wilson has a sort of quasi-cameo as Rosemary Cross's dead husband, Edward Appleby. When Max Fischer visits Miss Cross in Appleby's boyhood bedroom, photographs of a young Owen Wilson are incorporated in the set for the scene.
Wilson quickly landed roles in big-budget movies such as The Cable Guy, directed by Ben Stiller, an early admirer of Bottle Rocket. After minor appearances in action films like Anaconda, Armageddon and The Haunting, Wilson appeared in two dramatic roles: supporting actor in Permanent Midnight, which starred Stiller as a drug-addicted TV writer; and a role as a serial killer in The Minus Man.
Owen is considered a part of the Frat Pack, a group of actors including Steve Carell, Will Ferrell, Ben Stiller, Jack Black, Vince Vaughn, and brother Luke Wilson.
Owen got his big break with the 2000 comedy action hit Shanghai Noon, starring opposite Hong Kong action star Jackie Chan. The film grossed nearly US$100 million worldwide. His fame continued to rise after starring alongside Ben Stiller and Will Ferrell in the 2001 film Zoolander.
Gene Hackman took notice of Wilson's performance in Shanghai Noon and recommended Wilson to play opposite himself in the 2001 action film Behind Enemy Lines, Wilson's last dramatic starring role to date. Also in 2001, Wilson and Anderson collaborated on their third film, The Royal Tenenbaums, which was a financial and critical success. The comedy featured an all-star cast, including Gene Hackman, Ben Stiller, Bill Murray, Anjelica Huston, Gwyneth Paltrow, Danny Glover, Seymour Cassel and brother Luke. Owen Wilson had a memorable supporting role in the film as Eli Cash, a wigged-out, drug-addled bon vivant who becomes a literary celebrity. It earned the writing team an Academy Award nomination for Best Original Screenplay; Owen is the only "Frat Pack" member to receive an Academy Award nomination.
Wilson returned to the buddy comedy genre in 2002 with the action comedy I Spy, co-starring Eddie Murphy. This big-screen remake of the television series flopped at the box office. He then reunited with Chan to make Shanghai Knights (2003) and the movie remake of the television series Starsky & Hutch (2004). Due to his busy schedule as an actor and his ongoing sinus malady, Wilson was unable to collaborate on the script for Wes Anderson's fourth feature, The Life Aquatic with Steve Zissou. The 2004 film was ultimately co-written by filmmaker Noah Baumbach. However, Wilson did star in the film as Bill Murray's would-be son, Ned Plimpton—a role written specifically for Wilson.
Wilson partnered with Vince Vaughn in the 2005 Wedding Crashers which grossed over $200 million in the US alone. Also in 2005, Owen collaborated with his brothers by appearing in The Wendell Baker Story, written by brother Luke, directed by Luke and brother Andrew. In 2006, Wilson provided the voice of Lightning McQueen in the Disney/Pixar film Cars, starred in You, Me, and Dupree with Kate Hudson, and appeared with Stiller in Night at the Museum.
Wilson has appeared in eight movies with Stiller (a long-time friend) to date: The Cable Guy (1996), Permanent Midnight (1998), Meet the Parents (2000), Zoolander (2001), The Royal Tenenbaums (2001), Starsky & Hutch (2004), Meet the Fockers (2004) and Night at the Museum (2006).
Wilson's most recent release, another Wes Anderson film, The Darjeeling Limited, screening at the 45th annual New York Film Festival, the Venice Film Festival, opened September 30, 2007, co-starring Jason Schwartzman and Adrien Brody, in which three brothers take a train trip through India.
Bio from http://www.wilson-brothers.com
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Reviewer
His sense of timing and visual performance is outstanding. He is a joy to watch and can play serious roles with equal skill.
Only problem with him, star penalty, is he does come across a bit as a method actor, too much of his personality comes through in his characters; in many cases, this is fine but too often can be annoying.