Stiller and Wilson don their best '70s garb as they team up for the sixth time in Starsky & Hutch, which also features Carmen Electra and Vince Vaughn. The duo spoofs much of the original series and even features Wilson – whose voice needed to be altered by a computer to keep it on pitch – singing "Don't Give Up on Us," a #1 single in 1977 by the original "Hutch," David Soul.
PEOPLE names Wilson one of its 50 Hottest Bachelors. At the time, Wilson is dating salsa dancer Carolina Carisola, who appeared in Justin Timberlake's "Senorita" video and was the star at L.A.'s trendy burlesque club Ivan Kane's Forty Deuce. "What's sexy about Owen? Oh, I mean everything as far as I'm concerned. Owen has that little-boy-lost kind of thing about him," Wedding Crashers costar Jane Seymour tells PEOPLE.
Wilson and Vince Vaughn take the box office by storm with the huge success of Wedding Crashers. The film, also starring Rachel McAdams, earns more than $209 million, making it the second-highest grossing R-rated comedy in history (after Beverly Hills Cop). It's the biggest success in a string of films by Hollywood's new "frat pack," a collection of actors that includes Vaughn, Stiller, Luke Wilson and Will Ferrell.
As Dupree in the underachiever comedy You, Me and Dupree, Wilson plays a mid-30s slacker who moves in with his newly married friend (Matt Dillon) and his wife (Kate Hudson), causing trouble in the process. In real life, Hudson splits from her husband Chris Robinson in August, and reports surface connecting her to costar Wilson. In a joint statement to PEOPLE, Hudson and Robinson say "our reasons for separating have nothing to do with any third party."
Wilson and Hudson keep their distance after the media storm sparked by her separation, but they eventually become frequent companions, spending time together at Hudson's Pacific Palisades home and various L.A. hotspots. The two also vacation in Hawaii at the same time with Hudson's son, Ryder.
Though their relationship seems to cool over the winter holidays, Wilson and Hudson are spotted in Australia, attending the wrap party for Hudson's film Fool's Gold and biking together. In June, they call it quits just before Memorial Day weekend.
Wilson, 38, is transported to Cedars-Sinai Medical Center in L.A. to recover from an attempted suicide. He issues a statement pleading for privacy while he heals "during this difficult time." The actor drops out of the comedy Tropic Thunder, costarring his longtime pal Ben Stiller, and cancels an appearance to promote his new movie The Darjeeling Limited.
After appearing at the L.A. premiere of The Darjeeling Limited, Wilson slowly moves back into the public eye. He is spotted throughout New York City with Lance Armstrong and Jessica Simpson. "Everyone wants him to succeed," a family friend tells PEOPLE. "But they're letting him do it on his terms." In 2008, after hanging out with model Le Call, Wilson briefly rekindles his romance with Kate Hudson.
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