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Vince Vaughn was one of the signature comedy stars of the “Frat Pack” generation that emerged in the early 21st century, and remains one of the funniest actors on the planet. While Vaughn got his start in more grounded thrillers like Psycho and even tried his hand at being an antagonist in Domestic Disturbance, he found his place as a comedy actor, developing strong partnerships with both Owen Wilson and Jon Favreau.
Vaughn is unique among the comedy actors of his generation because he has evolved with the times; although he has found a place for himself with both streaming films and the independent thrillers of S. Crag Zahler, Vaughn also delivered one of his best performances to date on the Apple TV series Bad Monkey. Nonetheless, it is his film works for which he will always be best known for.
‘Old School’ (2003)
Old Schoolis one of the first great comedies of the 21st century because it defined the career of Todd Philips, a highly influential filmmaker who launched many of the great comedy stars of their time. Although Luke Wilson was already a star thanks to his work with Wes Anderson and Will Ferrell was getting popular thanks to his role on Saturday Night Live, Vaughn ended up being the surprising scene-stealer.
Old School succeeds as a classic underdog story that is raunchy, ridiculous, and surprisingly satirical, as Phillips is able to both lambast and celebrate his characters. Although Vaughn is cast in a role that could have very easily been completely unlikeable had the wrong actor been given the role, his ability to play fast-talking, charismatic characters helped him to develop an onscreen persona that he would retain for the next two decades.
‘Freaky’ (2020)
Freakyis an underrated horror film that likely would have been more popular had it not been dumped in theaters in late 2020 when most cinemas were still closed or barely operating as the result of the COVID-19 pandemic. The film offers a hilarious switch on the “body swap” comedy premise of Freaky Friday that combines it with the slasher sensibilities of Friday the 13th; Vaughn plays a ruthless killer whose mind becomes swapped with that of an awkward teenage girl Kathryn Newton.
Vaughn is able to give a surprisingly nuanced performance as a socially distraught teenager and gives far more pathos than the role required to simply be funny; while it could have easily been a film reliant on a silly gimmick, Vaughn transformed it into a truly memorable experience that was just as funny as it was scary.
‘Starsky and Hutch’ (2004)
Starsky and Hutch is another collaboration with Phillips that satirized a classic television buddy cop adventure, with Owen Wilson and Ben Stiller in the lead roles. Even though Vaughn and Wilson would go on to team up in several comedies, their roles were somewhat opposite in Starsky & Hutch; Vaughn was able to play the role of a menacing drug kingpin that is the target of a criminal conspiracy.
Vaughn walks a fine line of being just intimidating enough for Starsky & Hutch to succeed as an action film while still providing a fair amount of his signature brand of humor. It’s rather unfortunate that Starsky & Hutch never earned a sequel, as it is easy to imagine Vaughn getting more to do within later installments in the series, similar to what Mike Meyers did with the role of Dr. Evil in the Austin Powers franchise.
‘Dragged Across Concrete’ (2019)
Dragged Across Concreteis an unforgiving and provocative crime thrillerthat deconstructs the heist genre with an extremely dark brand of humor. Zahler, a filmmaker known for adding exploitation sensibilities into his genre films, turns a straightforward dirty cop thriller into a bizarre hangout story in which two corrupt police officers (played by Vaughn and Mel Gibson) experience the worst night of their lives after a botched robbery.
Vaughn is surprisingly effective as a self-loathing underling who is subservient to his partner, despite wanting to break out of his life of corruption in order to provide for his girlfriend. It’s an impressive performance because Vaughn is able to portray a loathsome, deeply brutal character who is nonetheless completely vulnerable. It’s the type of performance that shows why he has so much potential to experiment when given the chance to do supporting roles.
‘Fighting With My Family’ (2019)
Fighting With My Familyis one of the best films ever made about professional wrestlingbecause it understands the creation of characters needed to participate in the WWE. Although the film does feature a very fun performance by Dwayne Johnson as himself, Vaughn gives a heartfelt performance as a mentor to the film’s protagonist Paige (Florence Pugh), who tries out for the WWE alongside her brother (Jack Lowden) in order to fulfill their family’s legacy as wrestlers.
Vaughn is quite funny and charming, but he also shows a level of respect for professional wrestling and the importance it plays in many people’s lives. It’s also a supporting performance that doesn’t overstay its welcome; unlike many other A-listers of his generation, Vaughn has shown a keen sense of self-awareness, and can disappear into a role without trying to steal the spotlight for himself.
‘Hacksaw Ridge’ (2016)
Hacksaw Ridgeis one of the most brutal World War II films of the modern era, and served as a comeback for Gibson, who earned nominations at the Academy Awards for Best Picture and Best Director. Andrew Garfield received a nomination in the Best Actor category for his moving portrayal of Desmond Doss, but the entire ensemble does a great job at showing the brotherhood that forms among soldiers who served together during the Pacific Theater era of the conflict.
Vaughn is powerful in the role of a grizzled sergeant who nonetheless shows both leadership and empathy for Doss, who proves his worthiness in combat by saving lives as a medic. It’s one of the few films that truly maximizes Vaughn’s talent as a physical performer, as his height and strength make him appropriate to place menacing figures of authority.
‘Brawl in Cell Block 99’ (2017)
Brawl in Cell Block 99is one of most underrated action films of the 2010s, as it does for prison dramas what John Wick did for revenge thrillers. Vaughn is absolutely ruthless as a criminal who is forced to go to prison so that he can assassinate a rival mobster, which leads him into a brutal feud with a powerful gang.
Vaughn does incredible hand-to-hand combat in the film, showing his commitment to the material by doing his own stunts. Despite the fact that he became most renowned for his fast-talking, witty character roles, he is equally as effective as a near-silent character who spends far more time brooding than making quips. Brawl in Cell Block 99 could have easily been a cheesy “midnight movie,” but Vaughn gives enough genuine emotion to the role that it succeeds as a compelling work of crime fiction.
‘Dodgeball: A True Underdog Story’ (2004)
Dodgeball: A True Underdog Storyis one of the more successful comedies of the early 21st century, as it is easy to forget what a box office hit it was. Vaughn has always been an actor who excels at playing underdogs who are in over their head, and Dodgeball: A True Underdog Story gave him an opportunity to play both a sympathetic good guy fighting for his independence and someone who could deliver no shortage of snarky one-liners.
Vaughn has a surprisingly reserved sense-of-humor, as he needed to be more calculating with his line deliveries when compared to the more over-the-top sense-of-humor from Jason Bateman, Justin Liong, and some of the other cast members. Given how many comedies of this era have not aged well, Dodgeball: A True Underdog Story holds up as an empowering story about an independent businessman facing off with a monopolized corporation.
‘Swingers’ (1996)
Swingers is not only the film that launched a “swing revival” and newfound interest in Las Vegas in the ‘90s, but one of the most important releases within the independent cinema movement. While it wasn’t a massive success at the box office immediately, Swingers became a hit on home media and quickly developed a cult following, with Vaughn’s character being easily the most quotable.
Swingers was written by Favreau, who also starred in the film and decided to cast Vaughn as his onscreen best friend; their real-life friendship is palpable, as Swingers is one of the wiser and more discerning films of its era about dating, told from the male perspective in a way that doesn’t feel toxic. While Favreau’s career launched as a result of Swingers and its model for success, Vaughn’s charismatic breakthrough role might be the film’s most outstanding legacy.
‘Wedding Crashers’ (2005)
Wedding Crashersis not only the funniest film Vaughn has ever been in but one of his most dynamic performances. Despite the fact that the characters that he and Wilson are playing are somewhat despicable, Wedding Crashers makes them worth rooting for because of how they stand out amidst a crowd of privileged, wealthy wedding guests.
Vaughn is saddled with the more difficult role in the film because his character does not have the endearing love story, meaning that he had to do more physical comedy and find humor in misery. It’s a film in which there have been rumors for two decades about a sequel, especially after it was re-released to great success; while the notion of Vaughn and Wilson teaming up once more is certainly exciting, it’s hard to imagine that a sequel could ever live up to the original.
