The second of three boys, Dallas native Owen Wilson is caught cheating on a geometry exam while in tenth grade. He is expelled and sent to military school in New Mexico for his junior and senior years. "We were good until we started getting into firecrackers and girls," younger brother Luke Wilson tells PEOPLE in 1998.
Wilson majors in English at the University of Texas, where he initially has no plan to pursue acting. "I thought maybe I could write," he recalls to the Los Angeles Times. "If things worked out nice, maybe I could write some short stories or a novel, maybe go into advertising, writing little jingles and stuff." He meets fellow student and aspiring filmmaker Wes Anderson in a playwriting class and soon after makes his theatrical debut in Anderson's student play, a comedy called A Night in Tunisia.
Wilson and Anderson generate buzz at the Sundance Film Festival with Bottle Rocket, a 13-minute short film written by the pair and starring Wilson and his brother Luke as wannabe criminals. The idea becomes a full-length feature and is sold to Columbia Pictures later that summer. The quirky comedy, which hits theatres in February 1996, isn't a critical success but does serve as the first film role for the brothers.
With a bit part in The Cable Guy, Wilson marks his first collaboration with Ben Stiller, who directs and appears in the film. Stiller casts Wilson in the film after seeing him in Bottle Rocket. "The audience was getting it, but I was laughing more than anyone else," Stiller tells the Los Angeles Times. "I thought, 'This is my sense of humor.'" The pair – now close friends who take road trips and hit nightspots together before Stiller's 2000 marriage – will work together in six more films, costarring as the leads in the 2004 remake of '70s cop show Starsky and Hutch.
While portraying a serial killer in The Minus Man, Wilson romances costar Sheryl Crow, who makes her acting debut in the film as the killer's first victim. While neither is very forthcoming about the relationship, Crow does give the Toronto Sun some details in 1999. "He's seen me play a lot. And he loves it," she says. "It's funny because he's only ever been to two rock concerts and one of them was mine."
Wilson plays Jackie Chan's neurotic, girl-crazy sidekick in Shanghai Noon, which earns $32.2 million in its first two weeks. "Owen is in a league of his own. And a world of his own," director Tom Dey tells Entertainment Weekly. "But I knew after the first take of the first scene – he's a star waiting to happen." They reprise their roles in 2003's Shanghai Knights.
Wilson stars as a Navy aviator shot down in Bosnia in Behind Enemy Lines, receiving $3 million for the performance. "Let's face it, it's really Owen's movie," producer John Davis tells the Los Angeles Times. "It's his first major leading role. He's going to get very expensive very quickly."
After cowriting Bottle Rocket and 1998's Rushmore, Wilson and director Wes Anderson team up to write The Royal Tenenbaums, a quirky comedy about a dysfunctional family. Playing family friend Eli Cash, Wilson stars with his brother Luke, Stiller and Gwyneth Paltrow. Anderson and Wilson receive Oscar, BAFTA and Writers Guild nominations for Best Screenplay.
Signed to star in the adaptation of the '60s TV series I Spy, Eddie Murphy is given a list of potential costars. "Eddie saw the name Owen Wilson on the list and said, 'I don't even need to meet this guy before we start filming," director Betty Thomas tells the Chicago Sun-Times. "'I want him because I really like his work. The kid is funny.'" With overwhelmingly bad reviews, the film fails to make half of its $70 million budget.
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