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15 Famous Movie Love Triangles

For this list of 15 standouts, the door was open to hallucinations, inanimate objects, and even different species.

This Means War

Hitting theaters today is McG’s This Means War, a frothy comedy that pits Chris Pine against Tom Hardy in the fight for Reese Witherspoon’s smiley affections (best of luck there, Chris). From Arthurian legend to Bridget Jones’s Diary, stories of smitten trios have flooded the popular landscape, each threesome casting its sinful shadow on boring old monogamy. For this list of 15 standouts, the door was open to hallucinations, inanimate objects, and even different species—which is not to say Ménage à Twilight was ever in the running.


Sabrina

Humphrey Bogart, Audrey Hepburn, and William Holden in Sabrina (1954)

Billy Wilder’s final Paramount film, which went on to a inspire a Sydney Pollack-directed remake, sees Audrey Hepburn play a chauffeur’s daughter ever-pining for the prince (William Holden) of the family that employs her father. When she finally nabs her playboy’s attention after going all Edith Piaf, he’s already set to wed, and older bro Humphrey Bogart swoops in to avert disaster. Sparks fly faster than film noir bullets, and we say: Not a bad fallback.


Chasing Amy

Ben Affleck, Joey Lauren Adams, and Jason Lee in Chasing Amy (1997)

Ben Affleck tries to get Joey Lauren Adams to give up fish, while Jason Lee tries to contain his raging man love for the future Mr. Gigli. This is Chasing Amy, Kevin Smith’s most deeply felt film, which brazenly tread across sexual gray area, and helped to usher in the modern bromance. Our trio never consummates the tricky criss-crossed union, but who can forget the kiss Affleck plants on Lee to pose the fateful three-way?


The Red Shoes

Anton Walbrook, Moira Shearer, and Marius Goring in The Red Shoes (1948)

Of course, Anton Walbrook’s impresario is more an asexual (or perhaps homosexual) representation of the creative ambition that propels Vicky Page (Moira Shearer), so one could just easily place the titular shoes at the apex of this triangle, which is completed by Marius Goring’s doting, devoted composer. A tragic expression of how you truly can’t have it all, The Red Shoes is in many ways the ultimate workaholic melodrama, intoxicating to that last mad dash of consuming love.


Fight Club

Edward Norton, Helena Bonham Carter, and Brad Pitt in Fight Club (1999)

So it was all in Edward Norton’s head. Don’t tell us you didn’t believe Tyler Durden (Brad Pitt) was as much a three-dimensional presence as Meat Loaf’s man boobs. Things get especially fucked up when Norton starts pressing girlfriend Helena Bonham Carter about her relationship with Pitt, a relationship that, despite all the perplexing condoms chucked into the toilet, doesn’t even exist. Well, it exists, it’s just that Norton, not Pitt, was the one flying through the Trojans. Get it?

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The Age of Innocence

Daniel Day-Lewis, Michelle Pfeiffer, and Winona Ryder in The Age of Innocence (1993)

Martin Scorsese’s masterful adaptation of Edith Wharton’s novel sees Daniel Day-Lewis second-guess the oppressive dictates of his high-society life, falling hard for Michelle Pfeiffer’s passionate, soon-to-be divorcée while trapped in an engagement to her bland, compliant cousin (Winona Ryder). As Scorsese’s camera pulses through the elaborate salons of New York’s elite circa 1870, he reels you into the environment’s influence, and what’s ultimately given up by all three tortured characters is the stuff of wrist-cutters’ nightmares.


King Kong

Fay Wray, Bruce Cabot, and Kong in King Kong (1933)

Bruce Cabot may be the man Ann Darrow falls for while voyaging to an island overrun with mutant beasts, but it’s the mighty Kong who literally snatches her up, and gains her sympathy in the process. It’s certainly true that Cabot’s got plenty of slick, Old Hollywood smolder, but, really, who can compete with a spirit-soaring date at the tippy-top of the Empire State Building?


Y Tu Mamá También

Gael García Bernal, Diego Luna, and Maribel Verdú in Y Tu Mamá También (2001)

In recent cinema, rarely has sowing one’s wild oats been more hormonally uninhibited than it is in Alfonso Cuarón’s Y Tu Mamá También, where poolside masturbation sessions and impromptu car sex are all in a day’s activities. Gael García Bernal and Diego Luna venture on to manhood after a passionate road trip with Maribel Verdú, but also after exploring their sexual relationship with each other. The affair paid off: Bernal and Luna are thick as thieves, next to be seen broadening Will Ferrell’s horizons.


The Piano

Holly Hunter, Harvey Keitel, and the piano in The Piano (1993)

Technically, there’s a quadrangle at play in Jane Campion’s The Piano, with Holly Hunter caught between not just Sam Neill and Harvey Keitel, but between the men and her beloved beached instrument as well. There’s hardly any love in Neill and Hunter’s arranged union, though, so we’ll scrap him and stick with Keitel and those precious 88 keys, who bare witness to the Bad Lieutenant’s continued ’90s nude streak. Art is again in the mix as the chief fulfiller of passion, so much so that Hunter finds herself literally bound to it in the third act.

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Pearl Harbor

Ben Affleck, Josh Hartnett, and Kate Beckinsale in Pearl Harbor (2001)

Oh, by all means, keep rolling those eyes. No one said these were the 15 Greatest Movie Love Triangles. Making a mockery of one of U.S. history’s most fateful days as well as the very nature of love itself, Michael Bay offers perhaps the most spectacularly awful triangle to hit the screen, dropping Kate Beckinsale between Ben Affleck and Josh Hartnett, then letting the winds shift as they may. One lover heads off to war, then the other is available, then he heads off to war and dies, and then the other is available again. Who does Kate love? Whoever’s home.


Showgirls

Elizabeth Berkley, Gina Gershon, and Kyle McLachlan in Showgirls (1995)

The moment Gina Gershon buys Kyle McLachlan a private dance with pro pole-licker Elizabeth Berkley, Vegas’s strip-show power couple gets all shook up, with Berkley easing her way into Gershon’s territory, waiting for the right moment to ride McLachlan like an epileptic rodeo champ. Of course, Berkley has her self-fabulized nails in Gershon’s flesh too, teasing out the head Godess’s inner dyke. Who doesn’t want to see the retiree sequel to this film? Where Berkley and Gershon sit around eating Doggy Chow in “Vur-seys” pajamas?


The Philadelphia Story

Cary Grant, Katherine Hepburn, and Jimmy Stewart in The Philadelphia Story (1940)

George Cukor’s comedy of remarriage casts Katherine Hepburn as a Main Line socialite aiming to seal the deal with a new husband after calling it quits with Cary Grant. But a drunken swim with magazine reporter Jimmy Stewart, along with Grant’s eager return, makes for serious delays at the altar, to say the least. Stewart won an Oscar for his performance, which is ironic seeing as he’s the film’s only real straight man, if you will.


Wild Things

Matt Dillon, Neve Campbell, and Denise Richards in Wild Things (1995)

“Never let the sun go down on an argument,” Matt Dillon grunts before getting Neve Campbell to make out with Denise Richards, and then bedding both girls. Nothing, as they say, is what it seems in the white trash, gator-skin potboiler Wild Things, including the twisted arrangement among these three cash-hungry unfortunates. Campbell was on fire in her Scream heyday, and Richards was on the rise, pre-Sheen. See this movie if you want to forever associate champagne with her naked breasts.

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The Dreamers

Eva Green, Louis Garrel, and Michael Pitt in The Dreamers (2004)

The only entry in this list to include siblings, Bernardo Bertolucci’s The Dreamers fools around with incest as it presents a trio of idealistic film buffs holed up in a hermetic, sexually exploratory existence against the backdrop of the student riots in 1968 Paris. A regular Jolie circa her Oscar win, Eva Green is so in love with her brother, Louis Garrel, while exchange student Michael Pitt has a jonesing for both siblings. Bertolucci delivers a beautiful bit of controversy, and the three performances are fiery and real, despite the whole scenario being more escapist than the movies that flood the dialogue.


The Graduate

Dustin Hoffman, Anne Bancroft, and Katherine Ross in The Graduate (1967)

What’s better than winning Katherine Ross’s hand in marriage? Winning Katherine Ross’s hand in marriage after boning her mother first. The Graduate always registers as a great gag of a classic film, held in high regard among so many demure favorites when it’s explicitly driven by sex, with a MILF, no less. In the sexiness department, Anne Bancroft has Ross’s competition licked, yet there’s great satisfaction when she’s bested in the end. The cross that blocks that chapel door is about as plain as symbolism gets, fending off that cradle-robbing jezebel.


Jules and Jim

Oskar Werner, Henri Serre, and Jeanne Moreau in Jules and Jim (1962)

A convoluted love story that swerves and zags long before it literally sails off a cliff, François Truffaut’s Jules and Jim puts Oskar Werner, Henri Serre, and Jeanne Moreau through the ultimate love-triangle wringer, complete with war, marriage, divorce, maternal abandonment, miscarriages, gunplay, and vehicular suicide. A direct precursor to at least two other films in this list, the Nouvelle Vague masterwork is incalculably influential, its list of followers worthy of their own sub-roster.

R. Kurt Osenlund

R. Kurt Osenlund is a creative director and account supervisor at Mark Allen & Co. He is the former editor of Out magazine.

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