Vince Vaughn Has Charted the Sad Trajectory of Entitled White Dudes Since ‘Swingers’

Trent made him a star, and for the last 25 years he’s played variations of that character, who have had a hard time coping with a shifting American landscape

Welcome to Misleading Men, a regular feature where we look back at the actors who ruled Hollywood for one brief shining moment.

I was a white straight guy in college in L.A. in the 1990s, so as you might imagine — and I’m now a little embarrassed to admit — Swingers became a beacon for me and my friends. None of us were actors, and we didn’t have the same kinds of misadventures that the main characters did, but I’ll confess that the film’s vision of single dudes navigating L.A.’s hipster corridors — always with a sharp outfit and a cutting remark — felt aspirational. The 1996 comedy focused on two friends — freshly dumped nice guy Mike (Jon Favreau) and ultra-confident ladies man Trent (Vince Vaughn) — and I saw a lot of myself in Mike, who was insecure and overly sensitive. I thought Trent was hilarious but also a bit of an asshole — the kind of guy I assumed women liked.

“We’re all Mikes, but we all want to be Trents,” Swingers director Doug Liman said in 2016, later adding that Trent’s unsavory qualities — his sexism and racial insensitivity — were his and screenwriter Favreau’s way of “rebelling against the political correctness of our time.” That second quote is cringey, but my younger self understands what he’s getting at because of what he says in the first quote. Even in college, I knew I was never going to be unflappably-cool Trent, but a large part of me thought I should be or I needed to be. Sure, Mike gets a happy ending in Swingers, but we don’t live in movies. In real life, bulletproof, swaggering dudes like Trent always seemed to be more successful. Swingers established a preposterous binary — you’re either a sad-sack or a dick — and not knowing better, I bought into it.

Swingers was Vaughn’s coming-out party after years of hustling to land parts. Favreau, who was also getting his start, wrote Trent specifically for his buddy, and he’s said that he based the character on him. Only Favreau knows how much of Vaughn is Trent, but since moviegoers hadn’t seen this tall, lanky, big-haired braggart before, it was easy to conflate the actor and the character. And the truth is, a quarter-century later, I still see Trent in just about every performance Vaughn gives. I don’t know Vaughn personally, so who knows who the real Vince is. But it’s been interesting to watch as Vaughn — who turned 50 this year — has played characters who represent how a Trent would grow up and face a changing world. In the process, you can chart the course of modern masculinity — specifically, all the entitled, slightly bro-y straight white dudes who don’t end up getting everything they want in life.

In recent years, Vaughn hasn’t been shy about his right-leaning ways. The actor provoked a backlash after being seen shaking Trump’s hand during this January’s college football national championship game, but he’s long been a Rand Paul supporter and buddies with Glenn Beck. (He’s also very pro-gun, saying in 2015, “It’s well known that the greatest defense against an intruder is the sound of a gun hammer being pulled back.”) 

I bring this up because his political leanings don’t seem that far removed from Trent’s presumed politics — or from those of his subsequent characters. There’s a charming dickishness he brings to his roles — the backslapping quality of an overbearing, gregarious dude who laughs a little too loud and tells off-color jokes because, c’mon, we’re all friends. But it’s also old-fashioned, conservative, plainly reactionary — a “boys will be boys” attitude that swims against the current of an increasingly more inclusive, progessive society. This worldview comes up in his interviews, like in 2000 when he was asked about how he stays motivated once he became a star after so many years of struggle:

“I think that I got a good sense of reality from my parents, who came from blue-collar backgrounds and yet were successful financially. My dad put himself through college, and he was the first generation off the farm. My grandfather is still a farmer. He gets up at four in the morning and works his ass off all day. Then, he has to go and work on the railroad all night to pay the bills to keep the farm running. My parents say, ‘That’s a man, Vince, you should respect. You be proud of him.’ I think it all comes down to working for your parents’ approval.”

The loudmouthed Vaughn of Swingers was enormously appealing — unfiltered and shameless, a big walking id — and he repeated the formula, a little less successfully, as the snarky comic relief in The Lost World: Jurassic Park, a.k.a. Trent vs. the Dinosaurs. But soon after, Vaughn sought to demonstrate that he could do more than just comedy, taking on a trio of roles as deranged, violent characters in Clay Pigeons, the Psycho remake and The Cell. They were men without Trent’s humor or joie de vivre — they were monsters — and Vaughn worked hard to separate himself from the roles he played. In that same 2000 interview, he said, “I’d like to make it clear that I don’t want to be branded ‘the serial killer guy.’ I have no fascination with those guys. You hear about people buying these paintings from John Wayne Gacy and stuff like that. I personally think that’s really wrong and sick. Someone’s kid got cut up by that guy and you’re going to hang that in your house?”

After that journey into darkness, Vaughn focused on what would seem like his bread and butter, funny films, but in hindsight the next string of movies hinted at a growing anger in the sorts of characters he’d play. Reuniting with Favreau for Made, a crime comedy, his fast-talking Ricky wasn’t amusing — he was a bitter guy whose youthful impetuousness was starting to curdle. In Old School, he played Bernard, a miserable thirtysomething who wants to hit the reset button on his adolescence, proposing to his pals that they start a fraternity. His gym owner in Dodgeball was a bit of a loser, behind on his payments and desperate to keep from going under. These guys were all, essentially, unremarkable white men, and Vaughn was able to turn white-dude discontent into hit comedies. 

It made sense that he’d work with Will Ferrell on Old School and Anchorman since the Saturday Night Live star has built his whole film career on portraying these sorts of aggrieved, entitled white guys — except Ferrell has always had a knack for letting the audience knew that he knew that the characters were jerks. For better or worse, Vaughn doesn’t stand outside his performances so overtly — they’re closer to the bone, less exaggerated, realer in a way. And so his characters’ bitterness hits a little harder — it’s funny but also feels like a genuine expression of anger at the world. Where Ferrell’s men are winners but fools — insulated in the bubble of their (temporary) success — Vaughn’s are 9-to-5 nobodies who are mad that life didn’t work out for them. 

Vaughn enjoyed his next big success with 2005’s Wedding Crashers — that same summer, he was also another wingman character in his old pal Liman’s Mr. & Mrs. Smith — where he played the horndog divorce attorney Jeremy, scamming on women at weddings with his best friend and coworker John. Owen Wilson played the Mike-like John, while Vaughn’s Jeremy was the Trent, the coarser, lewder, crazier of the pair. Much like Swingers, Wedding Crashers was a movie about male friendship that understood the less-appealing elements of bro culture — how men think of women as conquests or targets — but because it came out 10 years after that initial breakthrough, the passage of time gave the Vaughn persona more authority but also more poignancy. 

In Wedding Crashers, Vaughn isn’t the beanpole kid he was in Swingers — he’s filled out and more relaxed — and the fact that Jeremy is an adult makes his desire to keep crashing weddings pathetic rather than endearing. (A twentysomething guy can be forgiven for talking about “beautiful babies,” like Trent did in Swingers, but when a dude in his mid-30s is trying to scam babes, it’s alarming.) Wedding Crashers is very much about how the Trents of the world stumble into some kind of maturity. Only by growing up will they ever find true love and some semblance of sustained happiness.

Or maybe not: The following year, Vaughn made The Break-Up, or Trent Realizes Relationships Are Hard. It’s a revisionist romantic comedy, you might say, which has a clever premise involving a couple (Vaughn and Jennifer Aniston) who decide to break up but still live in the same condo they bought together. (Hey, they like their place, even if they can’t stand each other anymore.) The Break-Up examined how a certain type of manchild grapples with the complicated pain of an adult breakup — how you have to evolve from the childish impulse to despise your ex to accept that, sometimes, love doesn’t last. Because of his height and motormouth demeanor, Vaughn just naturally comes across as a lot — it’s hard to be subtle when you’re 6-foot-5 — and although the movie isn’t great, Vaughn stretched himself a little playing a guy who has to accept that he has feelings, the kind of thing Trent would have mocked him for endlessly. 

Unfortunately, after that, it seemed like Vaughn chose to stay away from such sensitivity — at least in his studio movies. He’s quite good in a small role as a blue-collar guy in Sean Penn’s Into the Wild, but more people saw him in Fred Claus, Four Christmases, Couples Retreat, The Dilemma, The Watch, The Internship (back with Owen Wilson) and Delivery Man. None of those movies are tolerable. At this stage, he just seemed to be coasting on the Vaughn persona, which was growing increasingly desperate, like that one middle-aged guy hanging out at the college party. 

Tellingly, in a 2011 episode of Parks & Recreation, the show’s two characters who most (incorrectly) thought they were players — Tom (Aziz Ansari) and Jean-Ralphio (Ben Schwartz) — spend some time brainstorming about a best-man speech Tom has to give. Jean-Ralphio’s suggestion: “Okay, this is what I would do: I would start with a joke. Joke. Vince Vaughn quote, obviously.” Of course those two idiots would think quoting a Vince Vaughn movie would be the height of awesomeness. (Even funnier, when Tom asks if it should be “Swingers or Crashers,” Jean-Ralphio confidently responds, “Fred Claus.”) Clearly, they are the children of Trent, which signaled to the audience what yutzes they really are — and, also, how shtick-y Vaughn’s routine had become.

Perhaps realizing the growing lameness of his pissed-off, aging frat-guy persona, Vaughn in recent years has shifted into more dramatic roles, a pretty common move for funnymen who want to prove they have depth. Intriguingly, though, he’s focused on projects with right-leaning filmmakers like Mel Gibson (Hacksaw Ridge) and S. Craig Zahler (Brawl in Cell Block 99, Dragged Across Concrete). The highlight of this period was Brawl in Cell Block 99, which came out about a year after Trump’s presidential victory, where he played Bradley, a criminal and former boxer who has to literally fight his way through prison in order to complete a mission for his bosses. Serious as a heart attack, the thriller made good use of Vaughn’s imposing build as he portrayed a hardened thug who takes his rage out on anyone who crosses him. It was a brutal, completely believable transformation, as if the actor was showing us just how much raw anger was inside his characters all along. 

Brawl in Cell Block 99 was also uncomfortably reactionary — you could easily view Bradley’s descent into hell as a metaphor for white working-class resentment in the face of America’s shifting demographics and outsourced jobs. The violence was gratuitous and ugly, and Bradley was an unrepentantly unlovable antihero. All of this seemed to please Vaughn. “I feel like there’s too much of a climate of people trying not to offend anybody,” the actor said back in 2017. “It’s always more fun when people are allowed to go with a feeling or a point of view or an expression defiantly.” 

That strain of un-PC-ness has been evident in Vaughn’s work from the start. But his films have also been a fascinating reflection of the evolving social standing of painfully average white men in popular culture. Back in the time of Swingers, the story of some random white bros looking for beautiful babies was a completely acceptable idea for an indie comedy. It’s hard to imagine such a film being as popular in 2020 when we’re starting to see a greater diversity of stories being told. It seemed fitting that for last year’s true-life sports movie Fighting With My Family, Vaughn played the past-his-prime (but sympathetic and supportive) coach to Florence Pugh’s aspiring wrestler. It was her story about her bright future, while Vaughn’s character had had his moment in the sun already. In recent years working with Zahler, where he’s had more substantial roles, he’s played guys who feel alienated from the world — America has changed, and they don’t like it or understand it. The fact that Vaughn is so compelling in these roles raises a couple questions: Is he so riveting because he understands these men so well? Or is it because we believe that he’s one of them himself?

In Swingers, one of Trent’s signature lines comes when he’s trying to build Mike’s confidence before he talks to a girl. Trent, all full of arrogance and bluster, the whole world in front of him, tells his pal that he’s got to be a badass. “When you go up to talk to her, man, I don’t want you to be the guy in the PG-13 movie everyone’s really hoping makes it happen,” Trent says, his voice rising in a sarcastically feel-good way before he turns deadly serious. “I want you to be like the guy in the rated-R movie, you know? The guy you’re not sure whether or not you like yet. You’re not sure where he’s coming from, okay? You’re a bad man. You’re a bad man. You’re a bad man.”

Basically, Trent advises Mike to be like him. We’re all Mikes, but we all want to be Trents — at least when you’re young. But the characters Vince Vaughn has played over the last 25 years — many of them extensions of his Swingers lothario — are a warning that, in the end, maybe it’s okay that we end up as Mike. At least the PG-13 guy isn’t so afraid of the world that he runs away from it.