Three to Tango, released in theaters on October 22, 1999, is a romantic comedy built on manners, misunderstandings, and modern anxieties about honesty and image. With a brisk wit and sincere charm, it brings together Matthew Perry, Neve Campbell, Dylan McDermott, and Oliver Platt for a breezy story about how pretending to be something you’re not can make discovering who you are that much harder.
Perry stars as Oscar Novak, an ambitious young Chicago architect striving to make his mark alongside his loyal business partner Peter Steinberg (Platt).
When they’re shortlisted to design a multimillion-dollar cultural center for powerful real estate magnate Charles Newman (McDermott), Oscar believes he’s finally on the brink of success.
But a misunderstanding changes everything: Newman assumes Oscar is gay and therefore trustworthy enough to watch over his secret mistress, Amy Post (Campbell)—a free-spirited artist unaware she’s part of the ruse.
As Oscar spends more time with Amy, their chemistry becomes undeniable, though she too believes he’s gay. What starts as a harmless act of deception spirals into comic chaos as Oscar’s career, reputation, and heart all teeter on the edge.
From awkward social outings to a citywide misunderstanding that turns Oscar into Chicago’s “Gay Professional of the Year,” the movie finds humor in exaggeration without losing its gentle empathy for all involved.
When the truth inevitably surfaces, the revelation becomes less about embarrassment and more about integrity—the courage to be honest with oneself and others.
Perry gives one of his most likable film performances, balancing Chandler Bing-style sarcasm with tenderness.
Campbell radiates warmth and intelligence, subverting the typical “girlfriend” role with her mix of idealism and independence.
McDermott’s slick businessman adds dimension to the film’s moral landscape, while Platt provides the steadying humor that keeps Oscar’s misadventures grounded.
John C. McGinley, Bob Balaban, Deborah Rush and Kelly Rowan round out the cast.
Its screenplay, co-written by Aline Brosh McKenna (The Devil Wears Prada), shows an early knack for blending satirical wit with romantic sincerity.
Matthew Perry and Neve Campbell in Three to Tango (Photo/Warner Bros.)
Reception for Three to Tango
Three to Tango grossed $4.4 million on its opening weekend, finishing eighth at the box office.
The film would gross $10.6 million in its theatrical run.
Legacy
Though Three to Tango met mixed reviews upon release, arriving at the tail end of Hollywood’s mistaken-identity boom, it has since gained appreciation as a snapshot of its era: a time when romantic comedies toyed with social roles and stereotypes while still aiming for heart.
Three to Tango endures as a charming, if modest, entry in the rom‑com canon: a film that turns confusion into connection and proves that love, like architecture, is strongest when built on truth.
