A native Texan, Wilson was born in Dallas in 1971. The son of an advertising executive and a photographer, he was raised with two brothers, Owen and Andrew. The three would all go on to make their careers in film, with Wilson discovering his love of acting while a student at Occidental College. In 1993, the brothers Wilson collaborated with Wes Anderson to make Bottle Rocket, which was initially a 15-minute short. The gleefully optimistic story of three Texans who aspire to become successful thieves, Bottle Rocket premiered at the 1993 Sundance Festival, where it attracted the attention of director James L. Brooks. With Brooks' help, the short became a full-length feature film released in 1996. That same year, Wilson also appeared in the coming-of-age drama Telling Lies in America.

After large roles in three 1998 comedies, Bongwater, Home Fries, and Best Men (the latter two co-starring Barrymore), Wilson went on to star in another three comedies the following year. The first, Dog Park, was a Canadian film directed by Kids in the Hall alum Bruce McCulloch and featured Wilson as one of a group of twenty-somethings undergoing the trials and tribulations of love. Blue Streak starred the actor as robber-turned-policeman Martin Lawrence's sidekick, while Kill the Man (which premiered at the 1999 Sundance Festival) cast him as the owner of a small copy center competing with a large chain store across the street.

Though he would stick closely to comedy through 2001 with roles in Charlie's Angels (2000) and Legally Blonde (2001), Wilson took a turn for the sinister in the thrillers Preston Tylk and Soul Survivors (both 2001), before reteaming with his brother Owen and Wes Anderson to give one of his best performances as Richie in The Royal Tenenbaums.

Rebecca Flint, All Movie Guide