Alright, pop that tape in the VCR, adjust the tracking if you need to (remember doing that?), and settle in. Tonight on VHS Heaven, we're revisiting a film that feels aggressively late-90s, shimmering with the frosted tips and optimistic sheen of the era: 1999's romantic comedy romp, Three to Tango. It might not have set the box office on fire, landing with a bit of a thud ($20.4 million gross against a $20 million budget, ouch!), but I bet more than a few of us caught this one on a fuzzy cable broadcast or grabbed the clamshell case off the "New Releases" wall at Blockbuster, drawn in by its very familiar, very famous faces.
### That Old Mistaken Identity Shuffle
The premise is pure, unadulterated 90s rom-com formula: Ambitious Chicago architect Oscar Novak (Matthew Perry, deep in his Friends-fueled superstardom) and his business partner Peter Steinberg (Oliver Platt, reliably excellent) are vying for a massive commission from wealthy tycoon Charles Newman (Dylan McDermott, radiating smug charm). Through a series of convenient misunderstandings involving a gossip columnist and a poorly timed compliment, Newman becomes convinced that Oscar is gay. Seeing this as non-threatening, Newman assigns Oscar the strange task of keeping tabs on his free-spirited artist mistress, Amy Post (Neve Campbell, fresh off dodging Ghostface in the Scream series). The complication? Oscar, decidedly straight, immediately falls head-over-heels for Amy, but must maintain his fabricated gay persona to keep his job prospects alive and stay close to her. Cue the awkward situations and comedic near-misses!
### Perry Does Chandler Bing, Architect Edition
Let's be honest, a huge part of the film's appeal (then and now) rests squarely on the shoulders of Matthew Perry. He essentially channels his beloved Chandler Bing persona – witty, sarcastic, physically awkward, perpetually flustered – into Oscar Novak. If you loved Chandler, you'd find plenty to chuckle at here. His timing is sharp, and he throws himself into the requisite slapstick moments with gusto. Watching him navigate the increasingly complex lie, especially during a scene where he's unexpectedly honored by the Chicago LGBTQ+ community, is peak Perry comedic panic. It's a performance that relies heavily on his established screen presence, which, depending on your tolerance for Chandler-isms outside of Central Perk, is either its greatest strength or a slight weakness. Did you know Perry actually injured his finger during filming and had to incorporate the bandage into some scenes? Just a little hiccup in bringing that Novak charm (or panic) to life.
Neve Campbell, transitioning from horror heroine to romantic lead, brings a warmth and down-to-earth appeal to Amy. She has decent chemistry with Perry, though the script sometimes forces her into the trope of being frustratingly oblivious to the obvious. Amy feels like a slightly underwritten "cool girl" archetype common in the era's rom-coms, but Campbell makes her likable. Dylan McDermott leans into the suave, slightly dangerous energy he perfected on TV's The Practice, making Newman a believable (if somewhat cartoonish) obstacle. And let's not forget Oliver Platt as Peter, who often gets the biggest laughs reacting to Oscar's predicament and navigating Newman's assumptions about their own relationship.
### A Product of Its Time (For Better or Worse)
Directed by Damon Santostefano (who would later helm flicks like Bring It On: Again), Three to Tango is competently shot, making good use of its Chicago and Toronto filming locations to create a glossy, big-city feel. The pacing is generally brisk, hitting the expected comedic and romantic beats. However, revisiting it now throws its late-90s sensibilities into sharp relief. The central comedic engine runs on Oscar's "straight man pretending to be gay" panic and the surrounding characters' assumptions and stereotypes. While likely intended as harmless farce back then, some of the humor definitely lands differently today, occasionally feeling dated or relying on tropes that haven't aged particularly well. It's a fascinating snapshot of mainstream comedy just before the turn of the millennium. Interestingly, one of the credited writers is Aline Brosh McKenna, who would later achieve massive success scripting The Devil Wears Prada (2006) – you can perhaps see glimmers of sharp observational humor here, even within the broader comedic framework.
The film tries to have its cake and eat it too, ultimately delivering a message about judging people and the importance of honesty, but it navigates some tricky territory getting there. It walks a fine line, and your mileage may vary on how successfully it pulls it off.
### The Verdict Rewound
So, should you dig out that (metaphorical) tape of Three to Tango? If you're nostalgic for late-90s rom-coms and have a soft spot for Matthew Perry's specific brand of humor, absolutely. It's a charming, if predictable and occasionally awkward, time capsule. The cast is appealing, there are genuine laughs to be had, and it delivers the kind of light, fluffy entertainment that filled multiplexes and video stores back in the day. It doesn't reinvent the wheel, and its central conceit feels very much of its time, but it coasts comfortably on the charisma of its leads.
VHS Heaven Rating: 6/10
The rating reflects a film that's undeniably charming thanks to its cast, particularly Perry doing what he did best, and offers some solid laughs. It’s held back by a formulaic plot and a central comedic premise that feels quite dated by today's standards, preventing it from being a true standout but making it a perfectly pleasant slice of late-90s nostalgia.
Final Take: Three to Tango is like finding that old mixtape you made in '99 – some tracks still hit, others make you cringe slightly, but listening definitely brings back a specific, fuzzy memory.