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Who would have thought an uncredited role in the 1994 crowd pleaser 'Rudy' would launch Vince Vaughn's enduring cinematic career? While the actor has branched out from his career-defining role in 'Swingers,' starring in dramatic films like 'Clay Pigeons' and Gus Van Sant's shot-for-shot 'Psycho' remake, Vaughn's portrayals as goofy, boorish man-children that toe the line between amoral miscreant and heart-of-gold best friend have been his most memorable characters.

With 'Couples Retreat,' Vaughn reunites with 'Swingers,' 'Made,' and 'Four Christmases' co-star Jon Favreau as a husband that tries to save his marriage by taking his wife to a therapy-filled tropical retreat. We thought it'd be a good time to take a look back at some of the actor's funniest moments. Who would have thought an uncredited role in the 1994 crowd pleaser 'Rudy' would launch Vince Vaughn's enduring cinematic career? While the actor has branched out from his career-defining role in 'Swingers,' starring in dramatic films like 'Clay Pigeons' and Gus Van Sant's shot-for-shot 'Psycho' remake, Vaughn's portrayals as goofy, boorish man-children that toe the line between amoral miscreant and heart-of-gold best friend have been his most memorable characters.

With 'Couples Retreat,' Vaughn reunites with 'Swingers,' 'Made,' and 'Four Christmases' co-star Jon Favreau as a husband that tries to save his marriage by taking his wife to a therapy-filled tropical retreat. We thought it'd be a good time to take a look back at some of the actor's funniest moments.

'Swingers' (1996)

The role that kick-started his career and turned him into every college guy's hero, Vaughn's portrayal of Trent, the brash, cocky yet supportive friend, has held up as one of the most iconic (and quoted) characters in modern movie history. New Vaughn fans can look here for the archetype to many of his future roles.

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"All the while, you're just really wondering, 'Are we gonna get hopped up enough to make some bad decisions?'" With equally cynical partner-in-crime Owen Wilson, Vaughn's unique dating style of crashing weddings to hit on bridesmaids probably set off light bulb moments for men all over the country.

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'Anchorman' (2004)

Vaughn's had bigger roles, but the infamous 'fight scene' from Adam McKay's 'Anchorman' ranks as one of his most memorable for its absurd, over-the-top carnage- and decapitation-filled mayhem.

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'Old School' (2003)

Put Luke Wilson, Will Ferrell and Vaughn in the same room to relive their college years and it's no surprise that this is one of the most popular comedies of the decade. Worth seeing for Vaughn's "I'm talking crazy, boy band ass" line alone.

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'Dodgeball' (2004)

As a friendly, down-on-his-luck gym owner about to lose his business, Vaughn finds an obvious way to come up with the necessary cash: win a dodgeball tournament, duh. OK, it's a little outrageous, but it's still Vaughn's most likable, sympathetic role on the list.

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Reuniting with 'Old School' director Todd Phillips, Vaughn goes the evil route as murderous drug kingpin Reese Feldman. It's hard to take him too seriously though with the '70s porn 'stache.

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'Swingers' director Doug Liman helmed this Hitchcock remake and brought Vaughn in as Eddie, the fast-talking assassin friend of Brad Pitt that still lives with his mom. At the time, the buzz was all about Brangelina, but Vaughn steals every scene he's in.

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