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In 2006, Wilson voiced Lightning Mc Queen in the Disney/Pixar film Cars, starred in You, Me and Dupree with Kate Hudson, and appeared with Stiller in Night at the Museum as cowboy Jedediah.

Wilson starred with Ben Stiller in twelve films, including The Cable Guy (1996), Permanent Midnight (1998), Meet the Parents (2000), Zoolander (2001), The Royal Tenenbaums (2001), Starsky & Hutch (2004), Meet the Fockers (2004), Night at the Museum (2006), and the sequels Night at the Museum 2: Battle of the Smithsonian (2009), Little Fockers (2010), Night at the Museum: Secret of the Tomb (2014) and Zoolander 2 (2016).

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 did not perform well at the box office.

Also in 2001, Wilson and Anderson collaborated on their third film, The Royal Tenenbaums, a financial and critical success.

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