Wilson's acting career began with the lead role in the short film 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 physician beau of a schoolteacher in Rushmore (also 1998), also directed by Anderson and co-written by brother Owen.
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