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Wilson then landed a role in The Cable Guy, directed by Ben Stiller, an early admirer of Bottle Rocket.
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. His fame continued to rise after starring alongside Ben Stiller and Will Ferrell in the 2001 film Zoolander.
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 appeared in another Wes Anderson film, The Darjeeling Limited, which screened at the 45th annual New York Film Festival, the Venice Film Festival and opened September 30, 2007, co-starring Jason Schwartzman and Adrien Brody.
Wilson's films have grossed more than In April 2002, the release of the album C'mon C'mon by former girlfriend Sheryl Crow features the song "Safe and Sound", which is dedicated to Wilson in the liner notes, and is said to be an account of Wilson and Crow's relationship.
His parents, of Irish descent, were originally from Massachusetts.
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.
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Sources are saying that his love life isn't currently his priority!