In Twenty 20-Fav, we’re spending 2025 examining the work of actor/director Jon Favreau. This week we’re going to look at Swingers, which finds Favreau making his own moves and making stars out of buddy Vince Vaughn and director Doug Liman.
There’s a slight generational divide at work in Swingers, and this writer is juuuust on the opposite side of it. Actually, calling that divide ‘slight’ is a fucking joke. Swingers is a movie about the kinds of guys stomping around in the mid-90s taking part in the nascent swing and lounge revival. There’s a five year window—roughly between 1994 and 1999—where a whole bunch of Gen-X dudes were just really into martinis, bowling shirts, girls in victory curls, and loud, lightly ska-adjacent swing bands. Sixties nostalgia may have hit the 90s like a tsunami, but the swing revival rode that wave for longer than it probably should have. In fact, I have a whole podcast whose running theme accidentally became examining this very phenomenon.
But right in the middle of all of that is Swingers, written by Jon Favreau at a point in his career where he realized that if he was ever going to make it in Hollywood, he had to do it for himself. Co-financed and (therefore) directed by an up-and-coming Doug Liman1, Swingers stars Favreau as a floundering actor named Mike, who’s spent the last six months in Los Angeles getting nowhere in auditions, but mostly pining for an ex-girlfriend who simply refuses to call him. He talks with his buddy Rob (Ron Livingston), who gives somewhat normal advice, but it’s his other buddy, the motormouthed wild card Trent (Vince Fucking Vaughn) who takes Mike under his wing and gives him pep talks, pointers, and the kind of generally terrible relationship advice that always seems to work like a charm in pretty much any 90s sitcom.
Trent takes Mike to Las Vegas to break him out of his funk, which only makes things worse, because literally everyone they meet can see right through their wiseguy bluster. The Vegas sequence that opens the film has become iconic; so iconic, in fact, that its lingering footprint in the culture led me to believe for years that was entirely what the film was. Instead, Trent and Mike’s evening in Vegas feels more akin to a piece of expertly staged cringe comedy. It is painful watching these two idiots roll into a Vegas casino and act like high rollers with three hundred dollars to show for it. It’s brutal seeing Mike try to pick up a cocktail waitress with a Voltaire reference, thinking it went over her head, only for her to toss it back in his face as an object lesson in never underestimating people’s intelligence.
The back and forth between Vaughn and Favreau in the opening act of this film sets up the dynamic for the entire movie, where Trent and a coterie of Mike’s other friends (among them PCU‘s Alex Désert) try to give Mike advice on either how to get over his ex, or how to pick up literally anyone else. This makes up the entire middle act of the story, as our gaggle of guys wander from house party to nightclub, mingling with random women, trying to score numbers, and just generally feeling out the vibe. This feels like a fairly accurate portrait of how young people in the mid-90s (and pretty much any moment in history up to that point) hooked up, and frankly, here in 2025, it all just looks kind of exhausting2.
There’s a moment where our crew exits a bar and some random guy bumps into Trent’s buddy Sue (Patrick Van Horn), and the ensuing volley of “fuck you”s escalates into Sue pulling a gun and threatening to shoot every last one of them. Trent and Mike rightly dress him down for being the kind of buzzkill who walks around with a gun in his pants, but this being the 90s, all is forgiven twenty minutes later when Mike walks into Sue’s apartment to find the whole gang piled onto Sue’s couch playing Sega Genesis hockey. What’s better than this? Guys bein’ dudes…
Favreau, of course, realizes that there’s only one way for this kind of nonsense to end, and that’s with the standard rom-com meet cute at The Derby. There, Trent and Sue look on as Mike takes his swing and chats up blonde bombshell Lorraine (Heather Graham). Mike quickly finds that Lorraine has a similar breakup sob story, somehow appreciates his affinity for Groucho Marx3, and can keep him on his toes (literally, in a fun little dance number during a Big Bad Voodoo Daddy show).
Trent, for his part, is just a whirlwind of bad vibes. Everything out of his mouth is some kind of pick-up artist horseshit. His intentions are clear, he’s just out to get laid. There’s an honesty in that, at least, but his advice falls on deaf ears. Mike doesn’t want just another one-night stand, he wants to get over one relationship and jump straight into the next. But Trent persists, giving Mike the tools to succeed and then sitting back to watch the magic happen. And then when the magic does happen? Oh man, Trent loses his fucking mind.
Vince Vaughn is the clear breakout star of this movie4. Having first met Favreau on the set of Rudy, the two hit it off and became buddies, and many of their conversations about life and dating and the film industry found their way into the movie. Vaughn plays Trent with all the undeserved energy of a trust fund baby who’s never heard the word ‘no’ in his entire life. Trent walks into every room acting like he owns the place, and by the end of any given scene he’s gotten exactly what he wanted out of it and moved on like a fucking locust. The most lasting effect of Swingers on the culture at large has been sanctioning Vaughn’s brand of buffoonery which, if you can’t tell, is not my cup of tea.
Shot on a modest budget of $250,000, the movie often has a ramshackle look to it, which adds to the feeling that Swingers is a documentary of Los Angeles in the mid-90s. Several scenes were filmed without any permits, utilizing a skeleton crew to get shots done quickly. You can tell, too, as a few scenes feature Mike and his buddies in random locations, like the side of the highway outside Las Vegas or a putting green in the middle of LA, speeding through their dialogue in case they have to make a break for it if the cops show up. Party and nightclub scenes feature the actual guests and patrons who were there when the crew showed up. They even shot Mike and Lorraine’s dance scene at the club where Big Bad Voodoo Daddy were already booked to perform anyway.
Swingers proved to be a hit on the indie circuit, despite Liman and Favreau failing to get it into the Sundance Film Festival. Miramax picked it up fairly quickly and made it into a hit, grossing $4.6 million, making back eighteen times what it cost to produce. If nothing else, Swingers, like Slacker and Clerks before it, became a textbook for how to get a decent-looking movie shot on the quick and for cheap. While I kinda think the dating scene bullshit has aged like milk, I can still respect the hustle that went into making it all happen.
THE FAVREAU DIMENSION
Jon Favreau wrote Swingers after becoming frustrated with his minimal gains in Hollywood. After Rudy, he took the leap of moving to Los Angeles, ending a relationship in the process. (Hey, just like Mike!) He lost all of his D-Bob/Gutter weight and really tried to make it as a serious actor with little to show for it. Those frustrations found their way into the film, as Mike and Rob compare horror stories about landing roles and such. Or in Rob’s case not landing roles, in a running gag about him auditioning for the role of Goofy at Disneyland5.
As the lead, Favreau turns Mike into an awkward bundle of nerves, at times almost pathologically down on himself. Then, at other times, Mike nearly seems on the verge of exploding. You can see a sort of quiet rage behind his eyes that frequently threatens to come out. And I’m fairly certain the only reason it doesn’t is because Vince Vaughn is already right there acting like an utter lunatic. The one thing Swingers doesn’t need is two Trents.
But this proved to be Favreau’s calling card for the next several years, putting him on the map in both the indie world as well as establishing him as a versatile bit player in bigger budget films. We’ll start to see see a few of those coming up soon.
FINAL RATING
3.5 stars (out of 5). S’still pretty good.
NEXT TIME: No time for Z-Boys.
- Liman’s first feature, Getting In, is so incredibly unavailable that the only way to watch it is on YouTube, courtesy of user GettingIn3316, whose entire channel consists of that one video.
↩︎ - Then again, this may be a personal preference, as even a mildly populated bar is enough to trigger my crippling social anxiety.
↩︎ - This, ultimately, is the most ridiculous thing about the movie. Show me a guy who has ever picked up a woman by referencing You Bet Your Life, and I’ll show you a fucking liar.
↩︎ - Steven Spielberg saw the dailies at one point and was so impressed with Vaughn that he immediately cast him in The Lost World.
↩︎ - When Rob tells his friends he’s auditioning to play Goofy, their response is a blasé, “Hey, get that Disney money.” Which is fun considering Miramax was owned by Disney at the time they bought the film, to say nothing of Favreau’s future role in making Disney all the money in the universe. ↩︎
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