Vince Vaughn’s Complete Transformation

Actor Vince Vaughn is many things to many people. To some, he’s the face of “Wedding Crashers,” the ultra-successful aughts comedy about a pair of bros who attend weddings uninvited as a way to pick up women. To other fans, he’s the star of “Brawl in Cell Block 99,” an ultraviolent movie about a prison riot. He’s also a family man, a producer, a Chicago sports fan, and anything else that makes him happy. “For me personally, I really don’t care to a large degree about people’s opinions,” he told the Los Angeles Times in 2020. “How I feel about my choices and what I’m doing, whether that’s in your work or in your own life — that is more of a focal point to me.”

In an August 2024 interview with The New York Times, Vaughn looked back at his early star persona, reconsidering all those magazine profiles that talked about how much he loved to go out on the town. “I was a guy who enjoyed going out with friends, and we would definitely go out to bars, but I was also an actor who loved to read and watch things,” he said. “I mean, I definitely had sides of me. I’ve had a very unique life. I had a lot of extreme experiences that gave me perspectives.” Over the course of his decades in the entertainment business, Vaughn has definitely been through a number of ups and downs. Read on to learn more about his many transformations.

If Vince Vaughn is anything at all, he’s a Chicago man. He was born and raised in Lake Forest, Illinois, a suburb of the Windy City, and both of his parents worked. As a result, Vaughn told Playboy in 2015 that he was put in a lot of activities to keep busy. “When I was younger, they said I could be hyperactive and unfocused. I probably would be medicated if I were growing up today,” he reflected. “My parents, thankfully, said no to all that.” Still, that meant he struggled in school. “I didn’t have the attention span to study and focus on things that weren’t of top interest to me,” he said.

As a child, Vaughn discovered a love of acting while at camp. “During the summer, I participated in several different programs,” he told Chicago Magazine. “The first acting I did was at the Gorton Community Center, in Lake Forest. You had to be 13 years old or younger to be in a play.” As he became a teenager, different things took priority. “I played sports and hung out with the guys,” he remembered. “I wrestled fifth, sixth, seventh, and eighth grades. I played football my freshman and sophomore years, and freshman baseball, but I wasn’t any great shakes.” Soon enough, acting came calling once more.

Vince Vaughn rediscovered his love of acting while in high school when a friend invited him to audition for a part in a movie about issues faced by teenagers. “My parents didn’t want me to go downtown. We lived in the suburbs,” he told Playboy. “The casting director asked me if I wanted to read for the part, and I did, and I got it.” From there, things continued to progress for Vaughn. He explained, “That led to getting an agent and taking all this seriously. I did improv classes, acting classes, and I started performing live in the city even though I was a minor.”

Because he was younger than the other people he was acting with, Vaughn felt like he didn’t fit in. He recalled those days while speaking with Chicago Magazine, remembering that all the other actors liked to go out and drink. “I was from the suburbs, and that made me an outsider,” he said. Soon, though, that was all about to change. “Once I graduated from high school, I was fortunate to book several very good jobs, including a national Chevy commercial, an industrial film for Sears, Roebuck on exercise machines,” Vaughn recalled. “Very quickly, I moved out to California.” Hollywood had come calling, and Vaughn soon found himself acting in roles like “The Fourth Man,” a CBS after-school special led by “A Christmas Story” star Peter Billingsley.

By the mid-1990s, Vince Vaughn had developed a number of important friendships with other up-and-comers, including actor/director Jon Favreau. Together they developed “Swingers,” a film drawn from Vaughn’s own experiences trying to make it in Tinseltown. “I was sort of into swinging music and that lounge scene and, of course, you know, Jon exaggerated for comedy’s sake,” he told NPR’s “Fresh Air” a few years later. “We always look at comedy sort of as an overcommitment to the ridiculous.”

The indie film was a success, and Vaughn’s career was off and running. In fact, he told NPR that traveling to promote the film was the first time he ever flew first class. He was awed by the entertainment options and the free-flowing champagne, much to the chagrin of his co-star. “I was just amazed that that was happening. And Favs was kind of embarrassed, like, you know, ‘Act like you’ve been here before,'” he said. “And my point of view was, ‘But I haven’t been here before. Why should I cheat myself out of this first-time experience?'”

For the film’s 25th anniversary, Vaughn reflected to CinemaBlend that “Swingers” represented a pivotal time in his own career. “I love when I see people who are younger giving themselves permission to write movies or make movies, because you’re sort of in a unique moment where you’re a part of it,” he said. “I think what made it unique for us was that we were kind of vulnerable.”

After “Swingers,” Vince Vaughn’s career was off and running. At first, films like “The Lost World: Jurassic Park” aside, Vaughn mostly kept to artistic, indie movies. He starred in Gus Van Sant’s remake of “Psycho,” for example, playing the iconic Norman Bates character. By the early 2000s, however, Vaughn had found his next niche: as part of the so-called “Frat Pack,” a group that included people like Owen Wilson and Will Ferrell, making comedies for bros.

In 2003’s “Old School,” Vaughn plays a party-loving family man who turns a home into a frat house, hoping to recapture his glory days with his buddies. “I hadn’t done a lot of mainstream comedies,” Vaughn reflected to GQ. “I think [director Todd Phillips] maybe had to show them an interview I did on a talk show or something to make them comfortable that I could do the comedy, so that was interesting for me, ’cause I had sort of come from comedy.” After “Old School” was a hit, no one doubted Vaughn’s comedic chops again, and roles in other Frat Pack films like “Dodgeball” soon followed.

In 2005, Vaughn starred in “Wedding Crashers,” one of the most iconic films of his career to date. In an interview with Plot Twist, Vaughn joked that he related to his character’s misogyny. “I connected with him right away,” he said. “His proclivity for regarding women as objects was something that resonated deeply with me.”

In the 2000s, as Vince Vaughn’s mainstream movie career really took off, he took a comedy tour out on the road. His Wild West Comedy Show brought Vaughn and some famous up-and-coming friends to 30 cities in 30 days, as chronicled in a later documentary called “Vince Vaughn’s Wild West Comedy Show: 30 Days & 30 Nights Hollywood to the Heartland.” In addition to clips of various standup sets, Vaughn manages to wring pathos from the tour, too. “You knew I was gonna pull on your funny bone,” he told an interviewer while promoting the film. “Did you know I would tickle the heart bone, too?”

While the other comedians performed standup sets, Vaughn poked fun at his bro-comedy persona by doing a number of karaoke sets. He also took questions from the audience. “It reminded how tough it is to be a stand-up comic,” Vaughn told Parade of his days on the road. “It’s grueling never knowing if the audience is going to think you’re funny. It’s soul-destroying when they don’t laugh.”

Vince Vaughn and Jennifer Aniston starred in “The Break-Up” together, a comedy that follows the waning days of a relationship instead of the early ones. Vaughn came up with the concept and was heavily involved in the film’s production, and he told LiveAbout.com that he was particularly happy with Aniston’s casting. “You know, when we were developing the screenplay, she was the only actor that I had in mind because she’s so good with comedy,” he said. “She’s also a very good actor and she also has a quality to her that just inherently she’s very likable. There’s a warmth to Jennifer.”

The film may have been about a breakup, but it was also the catalyst for a new relationship. Vaughn and Aniston began dating on set, attracting the attention of pop-culture fans everywhere. This was 2006, not long after Aniston’s pricey divorce from Brad Pitt, and her romantic rebounds were the talk of the town. “I find it to be ridiculous, but I don’t take it personally,” Vaughn told Chicago Magazine in 2007. “They’re just doing it to sell papers and magazines.”

When various tabloids printed rumors of an affair, however, he did take it personally. In October, Vaughn sued The New York Post, The Daily Mirror, and The Sun for printing lies. He and Aniston broke up anyway, several months later.

After Vince Vaughn’s relationship with Jennifer Aniston fell apart, he was afraid to date another celebrity. “I never enjoyed the paparazzi side of it,” Vaughn told Playboy. “You like someone and you’re spending time with them; that’s separate and that was all fine. But I really spent most of that time finding ways not to be drawn into the attention.”

As a result, Vaughn’s next love story was far more low-key. After meeting at a wedding, Vaughn struck up a relationship with Kyla Weber, a Canadian woman who isn’t part of the entertainment industry. They were engaged by 2009, when he appeared on “The Ellen Show” and gushed about his bride-to-be. “I’m really happy,” he said. “I met her through a good friend of mine, and she makes me laugh, and she’s wonderful.” He asked her to marry him on Valentine’s Day, thinking that at least he’d remember their anniversary date. “It would’ve been kind of weird to have talked about it, and then skip Valentine’s Day,” he joked.

They married in 2010 back in Lake Forest, Illinois, where Vaughn grew up. “I waited until I was a little older, and I’m glad,” Vaughn told Playboy. “Marriage is terrific, but it’s the hardest thing I think you’ll ever do. You have to really work at it and want it. I got to an age when it was something that seemed exciting.”