In essence, every successful film is the perfect triangle: Three acts – with the second and third following characters who try to live up to, or overcome what they were pegged as in the smaller, act one set-up.
For love triangle films, the shape's top component serves as the object of affection most often pursued by the two equal-matched foes resting beneath them. While some films give away who will end up with who through marketing/billing errors, others – like the following ten – always keep audiences guessing. Some even play fast and loose with what it means to be a film consumed with the power of three.
Cruel Intentions (1998)
Starring Sarah Michelle Gellar, Ryan Phillippe, and Reese Witherspoon, 1998's controversial adaptation of a 1782 French romance pits the former two as step-siblings in a taboo game of sexual proportions.
Per the request of Kathryn (Gellar), if Sebastian (Philippe) can "deflower" Annette (Witherspoon), then he can take Kathryn to bed. As is the case with many compelling love triangle stories, lines become blurred in Cruel Intentions when A falls for B while in the pursuit of C.
The Philadelphia Story (1940)
Before they were leading men in Hitchcockian thrillers, James Stewart and Cary Grant basked in the glory of their screwball comedy roots.
Alongside fellow Golden Age powerhouse, Katharine Hepburn, the pair vied for her love in this Oscar-winning film released during the heyday of the "comedy of remarriage" subgenre. Though the third act redemption of Grant's abusive ex-husband character would most certainly be omitted from any future remake, Stewart's performance and Donald Ogden's screenplay still stand the test of time.
Last Vegas (2013)
Earning $134.4 million on a $28 million budget, Dan Fogelman's ensemble comedy proved Hollywood veterans Robert DeNiro, Michael Douglas, Morgan Freeman, and Kevin Kline could still front a smash.
Perhaps lost behind the bachelor party theatrics focus of the film's marketing was Mary Steenburgen. The actress delivers a stellar performance as a casino lounge singer equally lusted after by both DeNiro and Douglas, whose characters have long-held contempt for each other over a similar, conquest-based rift from their childhood.
Spider-Man (2002)
After just missing on the lead role in Sam Raimi's trilogy-kickstarter, James Franco slid rather nicely into the role of Peter Parker's friend (and eventual foe), Harry Osborn.
In Spider-Man, it is clear Harry too has eyes for Mary Jane "MJ" Watson, and the pair even wind-up dating. Though fans could guess Peter would enter the mix due to the pair's storied relationship across years of comic book issues, the uncertainty still posed considerable interest from fans. Who was MJ into most: Peter, Harry, or Spider-Man?
Pearl Harbor (2001)
In lockstep with the Titanic-formula, Michael Bay's explosive-heavy rendition of a real-life tragedy was bound to be plentiful in the romantic entanglement department as well.
Ben Affleck and Josh Harnett play a pair of best friend pilots whose love for the same nurse (Kate Beckinsale) resulted in a drunken, bloody squabble. Such matters took an infinite backseat the following morning as the real battle broke out overhead.
Pretty In Pink (1986)
Before Just Friends (2005), Pretty in Pink cornered the market in friend zone cinema.
The Brat Pack installment starred Molly Ringwald as yet another high school princess cursed with an outer beauty that could not make up for her indecisive nature. So much so that the viewers ultimately decided who her character would end up with, as an early test screening presenting an alternative ending/romantic mate for Ringwald's Andie Walsh failed to meet fan approval.
Chasing Amy (1997)
Awakenings regarding sexual fluidity – and the concept of codependent love in general – fuels a genuine love triangle interpretation for the power trio featured in Kevin Smith's critically-acclaimed indie rom-dramedy, Chasing Amy.
Alongside Jason Lee (My Name is Earl) and Joey Lauren Adams, who earned a Golden Globe nomination for the film, Ben Affleck shines as a narrow-minded comic book writer. After a whirlwind romance, he comes to learn not only that he loves both his girlfriend and his best friend but that he may have to choose between them.
Sabrina (1954)
Similarly to The Philadelphia Story, much of Sabrina's success regarding its love triangle plot device is accredited to its star billing.
With two comparable above marquee men in Humphrey Bogart and William Holden, audiences were constantly unsure who would land the titular character (Audrey Hepburn). This is something that Sydney Pollack's 1995 remake inherently did not replicate.
Fight Club (1999)
Knowing the big split personality reveal, revisitors of Fight Club should easily conform to the notion and better appreciate the film's irony (see: The narrator's jealousy of Tyler and Marla Singer).
It is only through Marla – played by Helen Bonham Carter – that the narrator (Edward Norton) comes to realize there was technically never a romantic competition between him and Tyler (Brad Pitt) at all. Thus, walls come crashing down as his hand lies in hers without intervention from a third. A love triangle exploded, presumably burnt to a crisp with the wreckage.
The Graduate (1967)
What started out as one thing, became another entirely.
The Graduate regularly ranks on all-time greatest movie lists for a reason. Within the assessment of love triangle movies, one should expect more of the same. For though there was no timeline crossover between Benajmin's (Dustin Hoffman) courting of both Mrs. Robinson (Ann Bancroft) and Elaine (Katherine Ross), the fact that he pursued both within one Simon and Garfunkel-scored summer served as an intimate conflict for the ages.