‘Swingers’
In 1996, Vaughn and Jon Favreau starred opposite each other in the R-rated dramedy Swingers, a movie about a wannabe actor (Favreau) whose sweet-talking friend (Vaughn) tries to show him how to score with the ladies.
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‘Old School’
In 2003, Vaughn costarred with Luke Wilson and Will Ferrell for the R-rated comedy Old School. The three friends relive the college glory days by starting their own fraternity near their alma mater, which brings together a variation of party-goers.
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‘Dodgeball’
In 2004, Vaughn starred opposite Ben Stiller in the comedy Dodgeball. The actor played Peter LaFleur, a small business gym owner who creates a dodgeball team in the hopes of winning the $50,000 prize at a dodgeball tournament that would save his gym.
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‘Starsky & Hutch’
Vaughn appeared opposite Ben Stiller, Owen Wilson and Snoop Dogg in the 2004 remake of 1975's Starsky & Hutch, a crime comedy about two cops who drive around in their Ford Torino catching criminals in the act with the help of Huggy Bear (Snoop). Vaugh played Reese Feldman, the drug lord antagonist.
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‘Wedding Crashers’
For the third time, following Zoolander and Starsky & Hutch, Vaughn and Owen Wilson teamed up for the 2005 comedy Wedding Crashers. The film follows two friends who crash weddings together in hopes of capitalizing on the available female romance at the ceremonies.
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‘The Break-Up’
Jennifer Aniston and Vaugh costarred in the 2006 comedy-drama-roamnce film The Break-Up. The pair played a couple that breaks up, yet continues to live together to avoid selling their condo. In continuing to live as housemates, their relationship dwindles and continues to get uglier.
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‘Into the Wild’
Starring opposite Emile Hirsch, Vaughn appeared in 2007's Into the Wild as Wayne Westerberg, a man who befriends traveler Chris McCandless (Hirsch) during his post-college hitchhike adventure.
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‘Couples Retreat’
In 2009, Vaughn performed opposite Malin Akerman in Peter Billingsley's Couples Retreat. The duo play a couple that joins three fellow couples on a tropical island vacation and partake in resort-required therapy.
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‘The Watch’
In 2012, funnymen Ben Stiller, Jonah Hill and Richard Ayoade, along with Vaughn, costarred in the comedic film The Watch. The film tells the story of four men who form a neighborhood watch group and end up defending the planet from an invasion by aliens that live among them.
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‘The Internship’
Owen Wilson and Vaughn partnered up again for the 2013 comedy The Internship. In the film, the comedic duo score an internship at Google and must compete with young and eager recent college graduates for an opportunity to work at the tech giant.