Vince Vaughn

Not Much of a Player

Outside of Chicago, Vince Vaughn plays football and wrestles in high school. "I didn't like it when they started yelling at you and started taking it real serious," he tells ESPN. "They were like, 'If you want it bad enough, run around the block,' and I realized that I didn't want it bad enough to run around the block." He turns to acting, lands a Chevrolet commercial, and moves to Hollywood in 1988.


Vince Vaughn

October 13

You're Money, Baby

While filming his first speaking role in the football flick Rudy, Vaughn meets costar Jon Favreau. They become quick pals. When Favreau writes Swingers, about a group of struggling actor pals, he uses Vaughn's real-life vernacular ("money," "honeys" and "babies") in his script. In 1996, Swingers becomes a low-budget, indie comedy with Vaughn starring as Trent Walker, a fast-talking, funny ladies' man.


Vince Vaughn


In Spielberg's Lost World

After seeing Vaughn in an early screening of Swingers, Steven Spielberg casts the unknown in his Jurassic Park sequel, The Lost World. "It's so strange to think, 'Okay, I'm going to work with Steven Spielberg and Julianne Moore,'" Vaughn tells Entertainment Weekly. The blockbuster grosses nearly $93 million its opening weekend


Vince Vaughn

November 06

A Brief Romance

Vaughn stars as the single father of a five-year-old in the drama A Cool, Dry Place. While the film doesn't generate much buzz, it does result in a brief relationship between Vaughn and his onscreen love interest, Joey Lauren Adams. Adams will appear onscreen with Vaughn again in The Break-Up, where she plays Jennifer Aniston's best friend. That December, Vaughn takes on the role of creepy killer Norman Bates in director Gus Van Sant's remake of the Alfred Hitchcock classic Psycho.


Vince Vaughn

April 10

Fist Swingers

In Wilmington, N.C. shooting Domestic Disturbances with John Travolta, Vaughn gets into a barroom brawl with several University of North Carolina students. Vaughn and three others are arrested, while costar Steve Buscemi, who is trying to break things up, is stabbed in the head, throat and arm and receives 35 stitches. "Vaughn was trying to fight everyone at once," a witness tells PEOPLE of the star who'll later reach a plea agreement that results in him undergoing alcohol counseling.


Vince Vaughn

February 21

Frat Pack

Costarring with Will Ferrell and Luke Wilson as a trio of thirtysomething guys who return to college to start their own fraternity in Old School, Vaughn reestablishes himself as a comic actor. "For a while before Old School came, I couldn't get any comedies," he tells the L.A. Times. "People would say 'Vince Vaughn's not funny' because I hadn't done anything since Swingers."

Vince Vaughn

March 28

Happy Birthday, Here's a Bloody Nose

Celebrating his 33rd birthday at L.A.'s Standard Hotel, Vaughn is standing outside the venue's lounge at 2:15 a.m. waiting for a ride home when a surly patron insults him. "Mr. Vaughn looked at him strangely, and the guy punched him in the face," Deputy Donald Mueller of the West Hollywood sheriff's station tells PEOPLE. The suspect breaks free and runs while Vaughn ends his night of revelry with a bloody nose but no further damage.


Vince Vaughn


Mr. & Mrs. Smith & Me

Playing Brad Pitt's sidekick in Mr. & Mrs. Smith, Vaughn gets a front row seat to the media frenzy over the burgeoning friendship between Pitt and costar Angelina Jolie. By the time the movie is released, Pitt and wife Jennifer Aniston have split, and PEOPLE has published shots of Pitt and Jolie rendezvousing in Africa.


Vince Vaughn

July 15

A Crashing Blockbuster

Vaughn and Owen Wilson crack each other up in the comedy Wedding Crashers with Rachel McAdams and Isla Fisher. The film rakes in $209 million, becoming the second-highest-grossing R-rated comedy of all time after Beverly Hills Cop.

Vince Vaughn


Just Costars?

Vaughn and Jennifer Aniston shoot The Break-Up near his hometown, Chicago. They play a split-up couple who refuse to move out of their condo. Vaughn begins spending time with his costar off the set, but denies rumors of a romance. "She is having fun in Chicago with Vince and the whole cast and crew," Aniston's rep Stephen Huvane tells PEOPLE. "Nothing romantic."

Photo Credits


Edited by Julia Wang

Vince Vaughn

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