Vince Vaughn’s style of humor was a popular flavor in the 2000s, appearing in many cult classic comedies of the era. Vaughn is recognizable for his immense height; at 6′ 5″, he dominates the scene, usually playing a wild but gentle giant who is memorable for having a nonchalant and laid-back attitude. He has a signature fast-talking, improvisational style that makes him spit rapid-fire jokes, leaving viewers rethinking what was just said.
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Although there are similarities between his characters, Vaughn is still a formidable force in the genre and one of the 21st century’s most influential comedic performers, especially in the R-rated territory. Indeed, over his thirty-year career, Vaughn has starred in multiple hit comedy movies opposite other beloved comedic actors, generating millions of dollars, earning decent reviews, and attracting a loyal following.
10 ‘Couples Retreat’ (2009)
Director: Peter Billingsley
Image via Universal Pictures
Couples Retreat revolves around four couples who embark on a tropical vacation to a luxurious resort called Eden. The couples join a therapy program with the expectation of enjoying the resort’s amenities but soon discover that participation in the therapy sessions is mandatory. The film explores the dynamics of each couple’s relationship, addressing issues such as communication, intimacy, and commitment.
While maintaining a comedic tone, Couples Retreat also delves into more serious aspects of relationships. Vaughn is the central figure who learns that even the most healthy relationships may need attention. Unlike other movies, Vuaghn has ample help here, with a stellar ensemble cast including Malin Åkerman, Jason Bateman, Kristen Bell, Jon Favreau, and Kristin Davis. It’s not a great movie by any metric—in fact, were it not for the cast, it would be arguably bad. However, Couples Retreat makes the most out of its stellar ensemble, becoming just entertaining enough to satisfy.
Couples Retreat
Release Date September 19, 2009
Runtime 107
Watch on Amazon
9 ‘The Dilemma’ (2011)
Director: Ron Howard
Image via Universal Pictures
The Dilemma aims to take the typical bromance scheme while adding more adult conflicts and situations. The plot concerns a man who has to tell his best friend that his wife is cheating on him. Alongside co-stars Kevin James, Winona Ryder, and Jennifer Connelly, Vaughn conjures enough star chemistry for the movie to be entertaining despite its obvious flaws.
Vaughn brings his trademark energy to guide an otherwise vapid script. While the pacing wavers, the actor does his utter best to bring the movie to life: he bumbles and bumbles until he is able to get out of the situation he is in. The Dilemma does offer a bit of heart but loses itself when elements of dark comedy come across as awkward instead of funny. And yet, The Dilemma remains a worthy comedy, largely because of the dynamic between its stellar cast, all consummate pros who know how to squeeze every last drop of juice from even the most bitter lemon.
The Dilemma
Release Date January 13, 2011
Runtime 118
Rent on Apple
8 ‘Delivery Man’ (2013)
Director: Ken Scott
Image via Walt Disney Studios Motion Pictures
Traces of Vaughn’s evolution into dramatics can be seen in Delivery Man. The film centers on David, a slacker delivery man for his family’s butcher shop who learns he has 533 children after making several sperm donations to a clinic during his student years. Worried his name will be exposed after a hundred of them take legal action, David must deal with the repercussions of his actions.
Delivery Man has plenty of typical Vaughn moments, but what he should be praised for is his levels of reacting to dramatic situations without being over the top. Despite such a large and potentially questionable comedic concept, Vaughn brings it down to Earth and makes it plausible, making a character that could easily be unlikeable fairly wholesome. While some of the moments are a little cliché when trying to pull on the heartstrings, Delivery Man is still funny and charming enough, all thanks to Vaughn’s commitment.
Rent on Apple
7 ‘The Break-Up’ (2006)
Director: Peyton Reed
Image via Universal Pictures
The Break-Up revolves around a couple, Gary Grobowski and Brooke Meyers (Jennifer Aniston), who decide to break up but continue sharing the same condominium due to financial constraints. The film explores the challenges and comedic moments that arise as they try to navigate their post-breakup living situation, learning to love each other a little more in the process.
Combining humor with moments of reflection on relationships and communication, The Break-Up offers a lighthearted yet surprisingly insightful take on the complexities of love and cohabitation. Vaughn and Aniston are incredible together, playing off each other while grounding the movie in something relatable yet humorous. Benefitting from their co-stars’ real-life relationship and the post-Friends success of Jennifer Aniston’s career, The Break-Up went on to gross $204 million at the box office, making it a surprise hit.
The Break-Up
Release Date June 1, 2006
Runtime 106
Watch on Tubi
6 ‘Four Christmases’ (2008)
Director: Seth Gordon
Image Via New Line Cinema
Vaughn starred opposite Reese Witherspoon in the holiday comedy Four Christmases. As the title implies, the film follows a couple who must juggle four different commitments during the holidays. On the premise of split families that have a little too much going on, Four Christmases reached a new audience who wanted something a little raunchier than the average holiday flick.
In the liminal space between being free to do whatever they want and starting a family, this film feels like another part of Vaughn’s evolution. Vaughn has several memorable scenes, like when he is about to throw up or when he plays Joseph in the Christmas pageant. However, what makes Four Christmases work is Vaughn’s ability to take his rambling and put it in a family environment, with his co-stars matching his energy with hilarious results. Four Christmases has aged quite well and is now often considered a modern holiday classic, adding another feather to Vaughn’s comedic cap.
Four Christmases
Release Date November 26, 2008
Runtime 82
Rent on Apple
5 ‘The Internship ‘(2013)
Director: Shawn Levy
Image via 20th Century Studios
Vaughn stars opposite Owen Wilson in the 2013 comedy The Internship. The two stars play salesmen who lose their jobs due to the digital age’s impact on traditional sales techniques. In an attempt to reinvent themselves, they secure internships at Google, where they must compete with younger and more tech-savvy interns, learning more about their business—and themselves.
The Internship explores themes of adaptation, generational differences, and the challenges of entering a highly competitive work environment. Starting as the bumbling oldtimer who gradually learns the way of innovation rather than standing in the dirt, Vaughn is in his element, sharing spectacular chemistry with Wilson and the younger cast. The combination of humor with a portrayal of the tech culture at Google creates a ripe environment for Vaughn and Wilson to do what they do best.
Watch on Hulu
4 ‘Old School’ (2003)
Director: Todd Phillips
Image via DreamWorks Pictures
The ultimate fraternity house movie, Old School tells the story of three friends—Mitch (Luke Wilson), Beanie (Vaughn), and Frank (Will Ferrell)—who decide to relive their college days by starting a fraternity near their alma mater. They encounter various challenges and absurd situations as they attempt to recapture the spirit of their youth. Vaughn’s character is unforgettable as the dad of the group, who contemplates hazing scenarios as he holds a baby to his chest.
The film explores themes of friendship, responsibility, and the desire to break free from societal expectations. The fish-out-of-water narrative helps set the scene for its humor, including Ferrell and Vaughns’ memorable performances as they navigate the world of fraternity life. Even with relatively new stars, the film was able to bring in $87 million at the box office, showing the talent that was burgeoning. Today, Old School stands as one of the best comedies from the 2000s and a worthy showcase of Vaughn at his fratty best.
Old School
Release Date February 21, 2003
Runtime 91
Watch on Paramount +
3 ‘Wedding Crashers’ (2005)
Director: David Dobkin
Image via New Line Cinema
The original mash-up between Wilson and Vaughn left an impressionable mark on their respective careers and the comedy genre as a whole. The iconic story of two divorce mediators who crash weddings to meet and pursue romantic relationships with women might sound ridiculous, and perhaps it is, which is only further testament to their celebrated talents. The pair follow a set of rules to successfully infiltrate various weddings, but their antics lead them into unexpected and often hilarious situations.
Wedding Crashers is an institution of the comedy genre in the 21st century. The film explores themes of love, commitment, and friendship while delivering laughs through its comedic situations and witty dialogue from the actors. The chemistry between Vaughn and Wilson is electrifying and non-stop-hilarious, each balancing their distinctive energy and enhancing an already funny screenplay. A proper icon of cinematic comedy, Wedding Crashers’ standalone reputation and delightfully noughties humor make it all the more enjoyable.
Wedding Crashers
Release Date July 13, 2005
Runtime 119
Watch on Max
2 ‘Dodgeball: A True Underdog Story’ (2004)
Director: Rawson Marshall Thurber
Image via 20th Century Studios
Dodgeball: A True Underdog Story is a sports comedy film where a group of misfits enters a dodgeball tournament to save their gym from being taken over by the ruthless White Goodman (Ben Stiller) and his fitness empire, Globo Gym. The movie comes to life with its quirky characters and intense dodgeball competition.
The humor often stems from its absurd and over-the-top characters, unexpected situations, and clever wordplay. Vaughn seemingly is the only one noticing the absurdity of his dead-pan reactions. Dodgeball embraces a mix of slapstick comedy, satire of sports and fitness culture, making it entertaining for a wide audience. The exaggerated personalities of characters like White Goodman and the unconventional underdog story contribute to the movie’s comedic appeal. And for a film with a budget of $20 million to bring in $168 million worldwide is quite the feat.
Dodgeball: A True Underdog Story
Release Date June 18, 2004
Runtime 92 minutes
Watch on Hulu
1 ‘Swingers’ (1996)
Director: Doug Liman
Image via Miramax
Swingers is about a group of friends navigating the dating scene in Los Angeles. Written by and starring Jon Favreau, the movie follows his character, Mike, and his friend Trent, played by Vaughn, as they explore relationships and nightlife. The independent feature had a budget of $200,000 and was able to gross $4.5 million, making indie stars out of both Favreau and Vaughn.
A cult classic of the 90s, Swingers is known for its witty dialogue, exploration of friendship and romance, along with its portrayal of the 1990s dating culture. The film’s often-quotable dialogue resonated with Gen X audiences, being praised for capturing a specific moment in time and showcasing the struggles and adventures of young adults navigating relationships. Vaughn is at his most effortlessly charming in Swingers, playing a one-of-a-kind character that arguably remains the highlight of his career.
Watch on Pluto TV
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