Vince Vaughn has had a long and fruitful career, mostly in comedy, though he mustn’t be underrated as a dramatic actor either. His role in True Detective Season 2 convinced people that Vaughn’s acting chops were made of more than just good comedic timing and charismatic one-liners. Though he’s made himself famous through plenty of independent movies, Vaughn also spoke about how comedy has changed from when he was at his peak on the YouTube hit show Hot Ones.
Indeed, Vaughn was the defining face of R-rated comedy during the 2000s (and even partly the 1990s), and his movies raised an entire generation; they don’t make them like that anymore, for better or worse. Watching Vaughn in new stuff or deciding to rewatch his greatest hits, he’s got some great feature films to boast about. Here are the best Vince Vaughn movies.
10
‘Clay Pigeons’ (1998)
Directed by David Dobkin
The underrated indie movie Clay Pigeons is a dark comedy centered around Clay (Joaquin Phoenix), his best friend’s wife Amanda (Janeane Garofalo), and Clay’s new friend, the mysterious and charming Lester (Vaughn). Clay and Amanda are having an affair and Earl finds out and decides to commit suicide and set up Clay. Clay continues seeing Amanda after hiding Earl’s body, and then he meets the quiet and reserved Lester, who hides a pretty dark secret.
Vaughn’s performance in Clay Pigeons is dark and twisted and early proof that he was always capable of going beyond comedy. Though the movie is a dark comedy, Vaughn has said that Lester’s trauma and conviction aren’t comedic at all; that Lester had convinced himself that he was a sane person in an insane world. Vaughn’s prowess in playing a dark character in Clay Pigeons came in handy when he was hired as Norman Bates for the remake of Psycho that same year.
Clay Pigeons
- Release Date
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September 25, 1998
- Runtime
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104 minutes
9
‘The Break-Up’ (2006)
Directed by Peyton Reed
You’ve never seen a rom-com like The Break-Up. This surprisingly raw relationship comedy stings by the time it ends, opening up some wounds for anyone who’s ever gone through a breakup with an unattentive partner. Vaughn co-wrote the script and decided to portray Gary, a travel agent who takes his relationship with girlfriend Brooke (Jennifer Aniston) for granted. After some time, Brooke begins to resent Gary’s behavior and lack of awareness to help around the apartment they bought together. In return, Gary resents Brooke’s need for perfectionism and control. Brooke leaves Gary, but since neither wishes to vacate the apartment, they continue living together in spite of each other.
The Break-Up was a commercial success, though critics didn’t feel the same way about it. Vaughn stepped into the role of a man whose flaws were the defining part of the relationship ending, and it was a small step away from the sort of good, funny guy or sarcastic man with a heart of gold trope he embodied over the years. Gary tries to repair what’s already broken so he’s not criticized for a lack of trying, but The Break-Up ultimately shows some things can’t be repaired.
8
‘Old School’ (2003)
Directed by Todd Phillips
Old School is frat-guy chaos at its best and a quintessential 2000s comedy. Vaughn’s character, Beanie, has pure “rowdy boy” energy—he’s smug, funny, totally unfiltered, and very likable despite it all. Old School unites some of the biggest comedians of the era: Vaughn, Will Ferrell, Luke Wilson, Jeremy Piven, and even Seann William Scott. The movie is about a group of friends opening a frat house near their alma mater so they can once again live like they did in their glory days.
Though critically panned and pretty much disliked, audiences loved the energy of the movie that was pretty much made for them. Around this time, we were getting used to Vaughn’s performances and acting style, and Old School seemingly defined a lot of his comedic performances around the time. The sort of carefree, goofy charmer became a template for Vaughn, who seemed like he was just getting funds to have fun with his friends—and nothing was wrong with that. This Vaughn era was iconic, and we all loved it.
Old School
- Release Date
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February 21, 2003
- Runtime
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88 minutes
7
‘Dodgeball: A True Underdog Story’ (2004)
Directed by Rawson Marshall Thurber
If you’ve never seen Dodgeball: A True Underdog Story, I recommend doing that as soon as you can. If you’re a true Vaughn fan, Dodgeball is a must-watch, mainly for its unhinged energy and hilarious performances, but also for its actual underdog-prevailing-over-the-favorite plot. Vaughn plays Peter LaFleur, the owner of a gym called Average Joe’s; Peter is an underachiever and a reluctant leader, but ultimately an inspiring figure to his friends. He enters a fierce and unusually well-funded competition of dodgeball against White Goodman (Ben Stiller), the smug and audacious owner of a mega-popular gym, Globo Gym.
The movie follows Peter gathering an unlikely crew of participants in a dodgeball tournament, training with them, and entering the competition as the unlikeliest team to win. The sports comedy is one of the most rewatchable comedies of the 2000s, just making you want to repeat the jokes and quotes of all the characters (though White Goodman is the most quotable, no doubt about it, with lines like “Nobody makes me bleed my own blood”).
6
‘Freaky’ (2020)
Directed by Christopher Landon
Freaky is a surprisingly great slasher comedy with Vaughn and Kathryn Newton. Both deliver brilliant performances, ensuring the movie is good, memorable, and surprising at moments. Vaughn plays a serial killer known as the Blissfield Butcher, while Newton portrays the bullied and ostracized high school girl Millie. One day, a bizarre turn of events makes the Butcher and Millie swap bodies, and now a deranged serial killer’s spirit is in the body of a teenage girl—and vice versa.
Vaughn’s ability to channel a terrifying character and a high school girl in the same movie was praised by critics and audiences alike, reminding them of his talents. Freaky shows just how much fun Vaughn can be when he swings big. Freaky is one of the better slashers with good performances all around, but it was slightly forgotten due to getting released around the time of COVID. After a short run in theaters, Freaky was released on streaming and ended up in a loop of endless movie scrolling. Go find Freaky on HBO Max right now and check it out.
Freaky
- Release Date
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November 13, 2020
- Runtime
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102 Minutes
5
‘Hacksaw Ridge’ (2016)
Directed by Mel Gibson
Vaughn united with Mel Gibson, who directed Hacksaw Ridge, portraying the role of a tough, layered sergeant. In a subdued but powerful performance, Vaughn shows up with sincerity and grit, showing off a great dramatic range. We knew he had it in him, but we were just impatient to see it happen. Hacksaw Ridge is one of the better war movies of the 2010s, tackling not just the journey of one brave soldier but carefully weaving themes of Christianity, faith, and perseverance.
Desmond Doss, the protagonist, was a real-life WWII participant, a field medic who, due to his religious beliefs, refused to carry a weapon into war. Doss survived, having lived until 2006; though he never saw the realization of the movie about his life, many people learned his story and grew to appreciate a person like him in a brutal, relentless, and violent setting. Andrew Garfield portrays Doss, earning an Oscar nomination, while Vaughn portrays his sergeant, who was adamant about dismissing Doss but ended up getting rescued by him after a fatal wounding.
4
‘Dragged Across Concrete’ (2018)
Directed by S. Craig Zahler
Dragged Across Concrete is Vaughn’s second time working with writer-director S. Craig Zahler; the two previously made Brawl in Cell Block 99, another one of Vaughn’s brilliant performances. Dragged Across Concrete is underrated, potentially because of a pretty long runtime (158 minutes) or maybe Mel Gibson, who’s been a bit on the outs over the past few years due to his reckless behavior. Still, Gibson and Vaughn, reuniting after Hacksaw Ridge, deliver a compelling duo of overzealous police detectives who use brutality against their suspects, as well as other unconventional and unethical questioning methods.
Dragged Across Concrete is a slow-burning, character-focused dark comedy that’s officially been recognized as a neo-noir thriller. Zahler wrote Bone Tomahawk as his directorial feature, and Dragged Across Concrete follows a similar, gritty and dark storyline filled with gray but memorable characters. Vaughn’s dramatic flair and unflinching ability to become a ruthless lead make him the star of the film. Is there anything he can’t do?
3
‘Brawl in Cell Block 99’ (2017)
Directed by S. Craig Zahler
It seems Zahler noticed how well Vaughn did as the antagonist of True Detective season 2 and decided to offer him the lead in his neo-noir action thriller, Brawl in Cell Block 99. The movie’s name might be the most tragic element, since it makes the movie sound like a Steven Seagal B-roll; however, Brawl in Cell Block 99 is anything but a B-movie. Vaughn underwent strict physical training to enter the role of the anti-hero Bradley Thomas, enjoying a career-defining twist. He’s brutal, brooding, and convincing in a movie that Zahler found an integral challenge for an actor of his caliber.
Brawl in Cell Block 99 follows Bradley, a recently fired mechanic who, out of a lack of opportunities, decides to turn to drug dealing under the crime boss Eleazar (Dion Mucciacito). About a year later, Bradley and Eleazar’s men get into a shootout with the police and Bradley gets arrested. Blackmailed and pushed around, Bradley vows to take revenge on Eleazar, who made him stay in prison for his sake. Brawl in Cell Block 99 is pretty brutal and heavy, but it’s a very fitting revenge movie that often pushes the limits of the extreme.
2
‘Wedding Crashers’ (2005)
Directed by David Dobkin
Wedding Crashers is an essential Vince Vaughn/Owen Wilson collaboration and a must-watch R-rated comedy of the 2000s. It’s peak Vaughn at his most chaotic and comedic best, stealing most of the scenes he’s in. He’s wild, unpredictable, and hilarious, defining a massive part of the movie’s energy. Wedding Crashers even helped the R-rated comedies come back to life, often being credited as a revival film. However, the movie is also a pretty interesting coming-of-age story, though the leads are very much of an age where they should be acting as adults.
Wedding Crashers follows Jeremy (Vaughn) and his best friend John (Wilson), divorce attorneys whose idea of a fun time is crashing people’s weddings. Noncommittal, brash, and rowdy, the men pick up girls at all these weddings, making notches in their bedposts wedding by wedding. Things turn south when Jeremy meets Gloria (Isla Fisher), who’s pretty clingy and a lovebug; Jeremy soon falls in love, and John’s left on his own in his ridiculous hobby. It’s a pretty cool movie, and one we love to revisit for the iconic Vaughn/Wilson energy.
1
‘Swingers’ (1996)
Directed by Doug Liman
“You’re so money, baby, you don’t even know it” is a phrase you’ve probably heard before but aren’t sure where or when. Well, Vince Vaughn says it in his slick and overly confident performance that made him a star and showed the world what this kid was made of—Trent Walker in Swingers. The longtime friendship between Vaughn and Jon Favreau was also noticeable in their chemistry while making Swingers; they’d been friends for three years or so at that point, and Favreau, who wrote the script for Swingers, based a lot of the movie’s characters on his friends.
Swingers is about a group of friends navigating life in Los Angeles during their 20s. The protagonist is Mike (Favreau), who moved to LA from NYC to pursue a comedy career and is getting over the breakup with his long-term girlfriend. Mike has a group of friends, and one of them is Trent, portrayed by Vaughn. Trent is the wingman you’d love to have, a real boost of confidence, energy, and bravado. He boosts Mike to flirt with women and get over his ex, but he has a lot of work to do on himself, too. If you like buddy comedies that will make you feel like you want to be friends with the guys in them, Swingers does a pretty great job of bringing the friend group’s dynamic closer to viewers.