15 Vince Vaughn Moments for the Comedy Hall of Fame

15 Vince Vaughn Moments for the Comedy Hall of Fame

Vince Vaughn is so indelible that it’s almost impossible to identify his most indelible performance. Swingers? Wedding Crashers? Old School? Dodgeball? All classics, and all classic Vaughn, each a slight variation on the fast-talking, sarcastic man-with-the-impromptu-plan that he cornered the market on in the late 1990s and early aughts.

For our part, we chose not to choose, which is why this list goes to 15. Here then is a good cross-section of his very best cinematic moments — a few somewhat serious, most very, very funny and all uniquely him…

‘Baby, You’re So Money, and You Don’t Even Know It’

The mid-1990s film that launched a thousand careers — from Vaughn’s, to Iron Man director and Mandalorian co-creator Jon Favreau’s, to Doug Liman’s, who went on to direct The Bourne Identity and Edge of Tomorrow. Still, despite all of that future star wattage (we haven’t even mentioned Office Space’s Ron Livingston), it’s Vaughn who undeniably steals the movie, and provided the cocksure motormouth archetype that would define the rest of his career. 

‘We Are on High Alert, Mom!’

Providing comic relief in Mr. & Mrs. Smith, also, a Doug Liman joint:

‘Where’s My Sugar, Darling?’

Clay Pigeons, a pitch-black comedy from 1999, may not be for everyone, but Vaughn gives one of the most unique performances of his career in it, going back and forth between kinda goofy and really creepy — and often combining the two.

‘I Built This Little Slice of Heaven With My Own Two Hands’

Critics and audiences weren’t kind to The Watch, but it does have a goofy, shut-off-your-brain guilty pleasure charm to it.

‘I’m Sitting in Blood! I’m Sitting in Blood!’

Couples Retreat was far from relaxing for Vaughn’s Dave:

‘He Is Way More of a Pirate Than You Will Ever Be’

Compared to the panoply of over-the-top characters in Dodgeball: A True Underdog Story, Vaughn seems downright subdued.  

‘You’re the Saint, and I’m the Piece of Sh*t’

Vaughn was an executive producer on the Netflix animated series F Is for Family, while also voicing recurring character Chet Stevenson. 

‘Have You Ever Seen Me Dress Like That?’

Freaky, a horror-comedy reimagining of the Freaky Friday body-swap trope, is way smarter than it has any business being.


‘There’s a Huge Cobra in There’

“Bathroom Cobra,” one of the many highlights from Vaughn’s stint as SNL guest host:

Extreme — Illegal — Couponing

In Queenpins, Vaughn is a U.S. Postal Inspector who teams up with a grocery-store loss prevention officer to stop a coupon counterfeiting ring. It’s the buddy-cop movie we didn’t know we needed. 

‘The Last One Goes to the Host, Everyone Knows That’

Here’s Vaughn going to toe-to-toe with another legendary misanthrope on Curb Your Enthusiasm:

‘Do You Think It’s Possible Your Mom Won’t Love You Anymore If She Sees How Badly You’re Losing at the Game?’

This scene from The Break-up is quintessential Vaughn, but the movie itself is also a surprisingly tender meditation on maturity (or lack thereof) and love. 


Vaughn’s Beanie in Old School is as if Trent from Swingers was all growns up: 

‘You Motorboating Sonofabitch, You Old Sailor, You’

The aughts were the golden age for raunchy, R-rated comedies like Wedding Crashers, and no one rode that wave better than Vaughn.

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