After minor appearances in action films like Anaconda, Armageddon and The Haunting, Wilson appeared in two dramatic roles: supporting actor 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 future girlfriend, singer Sheryl Crow was a co-star. The comedy featured an all-star cast, including Gene Hackman, Ben Stiller, Bill Murray, Anjelica Huston, Gwyneth Paltrow, Danny Glover, Seymour Cassel and brother Luke. It earned the writing team an Academy Award nomination for Best Original Screenplay.

Owen Cunningham Wilson (born November 18, 1968) is an American actor and writer, known for his roles in the films The Haunting, The Royal Tenenbaums, Zoolander, Meet the Parents, Wedding Crashers, You, Me and Dupree, Bottle Rocket, the Cars series, The Darjeeling Limited, Marley & Me, Midnight in Paris, Shanghai Noon, Behind Enemy Lines, and Drillbit Taylor. His family, originally from Massachusetts, is Irish American and Catholic. After minor appearances in action films like Anaconda, Armageddon and The Haunting, Wilson appeared in two dramatic roles: supporting actor 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 future girlfriend, singer Sheryl Crow was a co-star.

Owen Cunningham Wilson (born November 18, 1968) is an American actor and writer, known for his roles in the films The Royal Tenenbaums, Zoolander, Meet the Parents, Wedding Crashers, You, Me and Dupree, Bottle Rocket, the Cars series, The Darjeeling Limited, Marley & Me, Midnight in Paris and Drillbit Taylor Wilson was born in Dallas, to photographer Laura Cunningham Wilson and Robert Andrew Wilson, an advertising executive and operator of a public television station. Wilson attended the University of Texas at Austin where he graduated with a Bachelor of Arts in English. Wilson debuted as an actor in the role of “Dignan” in the Wes Anderson film Bottle Rocket, which he co-wrote with Anderson. After minor appearances in action films like Anaconda, Armageddon and The Haunting, Wilson appeared in two dramatic roles: supporting actor 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 future girlfriend, singer Sheryl Crow was a co-star.

He has an older brother, Andrew, and a younger brother, Luke, both also involved in filmmaking. Wilson subsequently landed a role in The Cable Guy, directed by Ben Stiller, an early admirer of Bottle Rocket. After minor appearances in action films like Anaconda, Armageddon and The Haunting, Wilson appeared in two dramatic roles: supporting actor 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 future girlfriend, singer Sheryl Crow was a co-star. in 2003. The film grossed nearly US$100 million worldwide. His fame continued to rise after starring alongside Ben Stiller and Will Ferrell in the 2001 film Zoolander. Also in 2001, Wilson and Anderson collaborated on their third film, The Royal Tenenbaums, which was a financial and critical success.