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After his film debut in Bottle Rocket (1996), Wilson co-wrote with Wes Anderson the script for Anderson's next two directorial films, Rushmore and The Royal Tenenbaums, for which they garnered an Oscar nomination for Best Original Screenplay.
Wilson then landed a role in The Cable Guy, directed by Ben Stiller, an early admirer of Bottle Rocket.
Gene Hackman reportedly took notice of Wilson's performance in Shanghai Noon and recommended the actor to co-star in the 2001 action film Behind Enemy Lines.
Also in 2001, Wilson and Anderson collaborated on their third film, The Royal Tenenbaums, a financial and critical success.
Wilson was born in Dallas, Texas, the middle of three sons of photographer Laura Wilson (née Cunningham) (born 1939) and Robert Andrew Wilson (1941–2017), an advertising executive and operator of a public television station.
His parents, of Irish descent, were originally from Massachusetts.
This big-screen remake of the television series did not perform well at the box office.
He made a cameo appearance in the Girl Skateboards video Yeah Right! He then reunited with Chan to make Shanghai Knights (2003), and co-starred in the film remake of the 1970s television series Starsky & Hutch (2004).
His older brother Andrew and younger brother Luke are also actors.After appearing in minor roles in action films like Anaconda and Armageddon and the horror film The Haunting, Wilson appeared in two dramatic roles: a supporting role in Permanent Midnight, which starred Stiller as a drug-addicted TV writer; and the lead role (as a serial killer) in The Minus Man, in which his future girlfriend, singer Sheryl Crow, was a co-star.