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.

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like Clay Pigeons R Crime Comedy Release Date September 25, 1998 Runtime 104 minutes Cast See All Joaquin Phoenix Clay Bidwell Vince Vaughn Lester Long Janeane Garofalo Agent Dale Shelby Scott Wilson Sheriff Dan Mooney Director David Dobkin Writers Matthew L. Healy Producers Chris Zarpas, Guy East, Nigel Sinclair, Ridley Scott Powered by Expand Collapse 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.

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like The Break-Up PG-13 Comedy Drama Romance Release Date June 2, 2006 Runtime 106 minutes Cast See All Venus Williams Serena Williams Where to watch Close WHERE TO WATCH Streaming RENT BUY Director Peyton Reed Main Genre Comedy Powered by Expand Collapse 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.

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like Old School R Comedy Release Date February 21, 2003 Runtime 88 minutes Director Todd Phillips Writers Todd Phillips, Scot Armstrong Where to watch Close WHERE TO WATCH Streaming Cast Vince Vaughn, Jeremy Piven, Will Ferrell, Ellen Pompeo, Luke Wilson Budget $24 million Studio(s) Paramount Pictures Distributor(s) Paramount Pictures, DreamWorks Distribution, Columbia Pictures Powered by Expand Collapse 7 'Dodgeball: A True Underdog Story' (2004) Directed by Rawson Marshall Thurber Close

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").

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like Dodgeball: A True Underdog Story PG-13 Comedy Sport Release Date June 18, 2004 Runtime 92 minutes Director Rawson Marshall Thurber Writers Rawson Marshall Thurber Where to watch Close WHERE TO WATCH Streaming

A group of misfits enter a Las Vegas dodgeball tournament in order to save their cherished local gym from the onslaught of a corporate health fitness chain.

Cast Vince Vaughn, Christine Taylor, Ben Stiller, Rip Torn, Justin Long, Stephen Root Main Genre Comedy Budget $20 million Studio(s) 20th Century Distributor(s) 20th Century Powered by Expand Collapse 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.

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like Freaky R Thriller Horror Comedy Release Date November 13, 2020 Runtime 102 Minutes Director Christopher Landon Writers Michael Kennedy, Christopher Landon Where to watch Close WHERE TO WATCH Streaming

In the movie Freaky, a high school student named Millie Kessler swaps bodies with a deranged serial killer known as the Blissfield Butcher. Millie must navigate the perils of being in the body of a wanted killer while trying to reverse the switch. She has only 24 hours before the change becomes permanent, leading to a thrilling race against time with the help of her friends.

Cast Misha Osherovich, Vince Vaughn, Celeste O'Connor, Kathryn Newton, Uriah Shelton, Dana Drori, Alan Ruck, Katie Finneran Main Genre Horror Budget $6 million Studio(s) Universal Pictures Distributor(s) Universal Pictures Powered by Expand Collapse 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.

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like Follow Followed Hacksaw Ridge R Drama Biography Documentary History War 10.0/10 Release Date November 4, 2016 Runtime 139minutes Where to watch Close WHERE TO WATCH RENT BUY Cast Sam Worthington, Rachel Griffiths, Richard Roxburgh, Andrew Garfield, Teresa Palmer, Matt Nable, Vince Vaughn, Luke Bracey, Nathaniel Buzolic, Hugo Weaving, Ryan Corr Director Mel Gibson Writers Robert Schenkkan, Andrew Knight Budget $40 million Studio(s) Lionsgate Distributor(s) Lionsgate, Summit Entertainment Powered by Expand Collapse 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?

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like Follow Followed Dragged Across Concrete R Thriller Action Adventure Drama Release Date March 22, 2019 Runtime 159 minutes Cast See All Mel Gibson Trezzo Mahoro Tory Kittles Thomas Kretschmann Director S. Craig Zahler Writers S. Craig Zahler Cinematographer Benji Bakshi Producer Keith Kjarval, Tyler Jackson, Jack Heller, Dallas Sonnier, Sefton Fincham Production Company Realmbuilders Productions, Assemble Media, Metrol Technology, Moot Point (Dragged) Productions, Unified Pictures, Look to the Sky Films, thefyzz, Cinestate Sfx Supervisor Alex Noble Budget $15 million Powered by Expand Collapse 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.

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like Follow Followed Brawl in Cell Block 99 NR Action Crime Thriller Release Date September 23, 2017 Runtime 132 Minutes Director S. Craig Zahler Writers S. Craig Zahler Where to watch Close WHERE TO WATCH Streaming RENT BUY

A brutal and intense drama featuring Bradley Thomas, a former boxer who finds himself in a maximum-security prison after a botched drug deal. To save his kidnapped wife and unborn child, Bradley must navigate the dangerous and violent world of the prison system. As he is drawn deeper into the prison's dark underbelly, he must engage in brutal confrontations and make tough decisions to protect his family. The film explores themes of sacrifice, loyalty, and survival, delivering raw and powerful action sequences within the confines of the prison.

Cast Vince Vaughn, Jennifer Carpenter, Don Johnson, Udo Kier, Dion Mucciacito Main Genre Action Budget 10000000.0 Studio(s) XYZ Films, Caliber Media Company, Cinestate IMDb ID tt5657856 TMDB User Rating 6 .977 Powered by Expand Collapse 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.

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like Wedding Crashers R Romance Comedy Release Date July 15, 2005 Runtime 119 minutes Director David Dobkin Writers Steve Faber, Bob Fisher Where to watch Close WHERE TO WATCH Streaming

Jeremy (Vince Vaughn) and John (Owen Wilson) are divorce mediators who spend their free time crashing wedding receptions. For the irrepressible duo, there are few better ways to drink for free and bed vulnerable women. So when Secretary of the Treasury William Cleary (Christopher Walken) announces the wedding of his daughter, the pair make it their mission to crash the high-profile event. But their game hits a bump in the road when John locks eyes with bridesmaid Claire (Rachel McAdams).

Cast Isla Fisher, Christopher Walken, Owen Wilson, Rachel McAdams, Jane Seymour, Vince Vaughn Budget $40 Million Studio(s) New Line Cinema Distributor(s) New Line Cinema Powered by Expand Collapse 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.

Your Rating close 10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Rate Now 0/10 Like Swingers R Comedy Drama Release Date October 18, 1996 Director Doug Liman Writers Jon Favreau Where to watch Close WHERE TO WATCH Streaming

Swingers follows a group of young, aspiring actors navigating the nightlife of Los Angeles in search of personal and professional success. As they explore the city's vibrant social scene, they experience the excitement and challenges of relationships and career aspirations, capturing a slice of mid-90s culture.

Cast Jon Favreau, Vince Vaughn, Ron Livingston, Patrick Van Horn, Alex Désert, Heather Graham, Deena Martin, Katherine Kendall, Brooke Langton, Blake Lindsley, Kevin James Kelly, Stephanie Ittleson, Vernon Vaughn, Joan Favreau, Rio Hackford Main Genre Comedy Powered by Expand Collapse

NEXT: Every Jon Favreau Movie Ranked By Box Office