Best Love Triangle Movies of All Time, Ranked
“Challengers,” Luca Guadagnino’s enthralling sports opera about three great-looking tennis stars who trade partners, is the latest movie to feature that time-honored configuration, the love triangle. And make no mistake: This one is complicated. It’s no mere either/or thing. But then, that’s always been true of the best movie love triangles. There’s an equality to them, a kind of symbiotic harmony. “Titanic” is a love triangle (and a timeless film), but it’s not like there’s much suspense about who Kate Winslet loves more, Leonardo DiCaprio or Billy Zane. You could say something similar of “Gone With the Wind.” But in the most haunting movie triangles, the triangle has an isosceles aspect; the angles exist in tantalizing balance. With that in mind, here are our picks for the 10 best love-triangle movies.
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10. Bull Durham (1988)
You might call Ron Shelton’s Minor League Baseball romance the “Challengers” of its day, as scripted by a cornball macho Preston Sturges. Tim Robbins, as a pitcher who’s gifted but wild (on the mound and in the sack), hooks up with hyper-literate baseball groupie Susan Sarandon. But it’s Kevin Costner, as the surly veteran brought in to show Robbins the ropes, who’s revealed to be the master of everything, from the Zen of baseball to the right angles of love.
9. Unfaithful (2002)
Diane Lane plays a suburbanite who sneaks away from her Hudson Valley dream home, and the husband and family she loves, to indulge in a cathartic affair with a weaselly French hunk (Olivier Martinez). That the fuddy-duddy husband is played by former heartthrob Richard Gere is the film’s first curveball. The second one is that the marriage winds up being held together by the very adultery that tears it apart.
8. Casablanca (1942)
Humphrey Bogart and Ingrid Bergman seem as made for each other as any couple in screen history. Yet they’re not a couple — they’re an ex-couple who will always have Paris. And Bergman’s husband, a WWII resistance fighter (Paul Henreid), needs her because she’s “the thing that keeps him going.” The deep meaning of this triangle is the way it crystallizes the place where love meets morality.
7. She’s Gotta Have It (1986)
It’s not technically a triangle — more like a quadrangle. But Spike Lee’s puckish first feature gives you that triangular tingle. It’s built around Nola Darling (Tracy Camilla Johns), a Brooklyn graphic artist who juggles three ardent suitors. Will she choose one, or will she choose the impulse to be free?
6. The Philadelphia Story (1940)
How’s this for a heady triangle? Katharine Hepburn, as the divorced daughter of a socialite family, is on the verge of getting remarried — and her fiancé isn’t even one of the suitors who matter. They would be Cary Grant, as her ex-husband, and James Stewart, as the gossip journalist who shows up to cover the wedding. Have there ever been two dreamier options? George Cukor’s classic is the perfect sophisticated romantic comedy, in part because the rivalry keeps us in suspense.
5. The Mother and the Whore (1973)
At this point you may be wondering: Where’s “Jules and Jim”? Sorry, but we think it’s a turgidly whimsical, overpraised movie. When it comes to French ménage dramas, we prefer Jean Eustache’s 3-hour-40-minute New Wave-meets-New Realism epic about three café bohemians (Bernadette Lafont, Jean-Pierre Léaud and Françoise Lebrun) who think that the freedom of connection they long for was promised to them by the hangover of the counterculture.
4. Reality Bites (1994)
Ever since the 1980s of “Pretty in Pink,” youth movies have been rife with love triangles (the “Twilight” films, “Wild Things,” “The Kissing Booth 2”). But Ben Stiller’s Gen-X landmark set the standard. Should Winona Ryder, as a budding filmmaker, go with the sweet nerdish music-channel executive (Stiller) or the slacker (Ethan Hawke) who’s a serious louse? The answer is obvious … until it isn’t.
3. Sunday Bloody Sunday (1971)
In John Schlesinger’s decades-ahead-of-its-time classic, Murray Head plays a bisexual sculptor carrying on two affairs at once: one with a brittle recruitment agent (Glenda Jackson), one with a Jewish physician played by Peter Finch with an ordinary-bloke melancholy that made him a groundbreaking figure in queer cinema. This triangle is no movie sculpture — on the contrary, it’s as complex as life.
2. My Best Friend’s Wedding (1997)
Julia Roberts plays a food critic who decides to sabotage the wedding of her best friend (Dermot Mulroney) — to yupscale princess Cameron Diaz — when she realizes she’s in love with him. Her destructiveness puts the audience in an exquisitely amused, jaw-droppingly squirmy position. Do we want to see her succeed? The triangular resolution is nothing less than transporting.
1. The Apartment (1960)
In Billy Wilder’s sublime office drama, insurance clerk Jack Lemmon loans out his Upper West Side apartment to his executive overseers, who use it for their adulterous trysts. When Lemon himself tries to court an elevator operator (Shirley MacLaine), only to learn she’s having a fling with his boss (Fred MacMurray), their triangle becomes a lightning rod channeling love, power, corporate dehumanization and the rise of women.
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