9 Vince Vaughn Movies You Have to See: From ‘Swingers’ to ‘Old School'

Vince Vaughn used his memorable role in the indie hit ‘Swingers’ to help him become one of Hollywood’s funniest leading men. In honor of his new comedy, ‘Unfinished Business,’ hitting theaters, let’s reunion tour with some of the actor’s more notable roles.

Though the part of college football player Jamie O’Hara was small, Vaughn made a memorable impression on another cast mate – his ‘Swingers’ costar Jon Favreau.

Playing wannabe actors trying to make it in Hollywood, Vaughn and costar Jon Favreau had their breakout roles in this 1996 hit, directed by Doug Liman. Vaughn’s performance caught the eye of many in Hollywood, most notably Steven Spielberg.   

Steven Spielberg cast Vaughn to play photo journalist Nick Van Owen in this sequel, which also stars Julianne Moore and Jeff Goldblum. The three find themselves outrunning several T-Rexes and raptors while paying a visit to the first island where the dinosaurs were beta tested.

Before he became a full-time comedic leading man, Vaughn costarred in this underrated drama about friendship and loyalty. After three friends party it up overseas, one of them (Joaquin Phoenix) gets caught with drugs and faces a death sentence unless the other two character’s -- Vaughn’s especially -- return to help serve jail time.

Vaughn and Favreau teamed-up five years after their first film together, this time playing low-level mob guys who take part in a money-laundering scheme. Written and directed by Favreau, the film is largely successful thanks to the actors’ effortless chemistry.

A staple of many college students’ DVD collections, ‘Old School’ put Vaughn on the path to a string of hit comedies, playing one of three middle-aged friends that relive their partying days by starting a fraternity at their old alma mater. Luke Wilson, Will Ferrell and, of course, “Blue,” also star.

Ben Stiller’s purple-clad fitness nut takes on Vaughn and his crew of misfits in the ultimate battle: A Las Vegas Dodgeball tournament. If you’re not referencing this movie’s highly-quotable lines daily, then you’re some king of wrong person.

Vince Vaughn and Owen Wilson play a pair of lifelong friends who share a passion for crashing weddings in order to pick up girls. One of the most successful R-rated comedies ever, the film gave a significant bump to Vaughn’s stardom – as well as helping launch Bradley Cooper’s big-screen career.

Then-real-life couple Vince Vaughn and Jennifer Aniston play two lovers trying to find the funny side of the titular conflict, in this movie that is equal parts comedy and drama.