Wilson's acting career began with the lead role in Bottle Rocket in 1994, which was co-written by his older brother Owen Wilson and director Wes Anderson. It was remade as a feature-length film in 1996. After moving to Hollywood with his two brothers, he was cast opposite Calista Flockhart in Telling Lies in America and made a cameo appearance in the film-within-the-film of Scream 2, both in 1997. Wilson filmed back-to-back romantic films in 1998, opposite Drew Barrymore, Best Men, about a group of friends who pull off a heist on their way to a wedding, and Home Fries, about two brothers interested in the same woman for different reasons. He played the doctor beau of a schoolteacher in Rushmore (also 1998), also directed by Anderson and co-written by brother Owen.
He starred opposite Reese Witherspoon in the 2001 comedy Legally Blonde, which was followed by Old School and The Royal Tenenbaums. Wilson also had a role on That '70s Show, as Michael Kelso's older brother Casey Kelso, appearing sporadically from 2002 through 2005.
In 2006, Wilson starred in Idiocracy, Mike Judge's first film since 1999's Office Space. He portrayed an ordinary serviceman chosen for a cryogenics project. He awakens after hundreds of years in an America which is significantly less intelligent. The film was initially dropped by Fox Studios, but re-distributed in 2006.
In early 2007 Wilson took a role opposite Kate Beckinsale in the thriller Vacancy. In July 2007, he worked on Henry Poole is Here in La Mirada, California. He starred in the film Tenure.
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