10 Best Love Triangle Movies That You Should Watching Update 04/2024

Best Love Triangle Movies

Whether it’s a romantic comedy or a drama, love triangles are a hallmark of cinema. The following is a list of the top 10 romantic movies with a trio of lovers.

It is a perfect triangle in the form of a successful picture. Third act follows characters that are trying to live up to, or overcome, what they were pegged as in the first act.

Top of the triangle serves as the object of adoration for the two equal-matched antagonists resting below it in love triangle films. Others, such as these eleven films, never let viewers guess who would finish up with whom due to marketing or billing problems. With the power of three, there are some who play fast and loose.

1. Cruel Intentions (1998)

Cruel Intentions (1998)

The 1998 version of a 1782 French romance starring Sarah Michelle Gellar, Ryan Phillippe, and Reese Witherspoon puts the former two as step-siblings in a taboo game of sexual proportions.

After Kathryn’s request, Sebastian (Philippe) can take Kathryn to bed if he can “deflower” Annette (Witherspoon). The lines in Cruel Intentions get blurred when A falls for B while pursuing C, just like in many compelling love triangle scenarios.

2. The Philadelphia Story (1940)

James Stewart and Cary Grant enjoyed success in screwball comedies before moving on to Hitchcockian thrillers.

During the zenith of the “comedy of remarriage” subgenre, Katharine Hepburn and Audrey Hepburn competed for her affections in this Oscar-winning picture. In any future remake, the third-act redemption of Grant’s abusive ex-husband character would be deleted, but Stewart’s performance and Donald Ogden’s writing remain timeless.

3. Last Vegas (2013)

Last Vegas (2013)

Dan Fogelman’s ensemble comedy demonstrated Hollywood veterans Robert De Niro, Michael Douglas, Morgan Freeman, and Kevin Kline could still front a smash. The film earned $134.4 million on a $28 million budget.

To some extent, the film’s promotion may have overlooked Mary Steenburgen. Both DeNiro and Douglas have long harbored resentment toward each other over a childhood rivalry that stemmed from their shared desire to win a high-stakes poker game.

4. Spider-Man (2002)

James Franco, who had just missed out on the lead part in Sam Raimi’s trilogy-kickstarter, was a natural fit for Harry Osborn, Peter Parker’s best friend and eventual antagonist.

Harry and Mary Jane “MJ” Watson end up dating in Spider-Man, making it evident that Harry has feelings for MJ as well. Despite the fact that many fans had guessed that Peter would be in the mix due to their long-standing connection, the ambiguity still presented a great deal of interest. Peter, Harry, or Spider-Man was MJ’s favorite?

5. Pearl Harbor (2001)

Pearl Harbor (2001)

When it comes to romantic entanglements, Michael Bay’s bombastic take on a real-life catastrophe was doomed to follow the Titanic-formula.

Ben Affleck and Josh Harnett star as best friends pilots who had a drunken, bloody dispute over a nurse (Kate Beckinsale) who they both fell in love with at the same time. The following morning, the true conflict erupted above, and all other concerns faded into the background.

6. Pretty In Pink (1986)

Pretty in Pink dominated the market for films about the friend zone prior to Just Friends (2005).

Molly Ringwald starred as yet another high school princess plagued with an exterior beauty that could not make up for her indecisiveness in the Brat Pack sequel. Viewers finally selected who Andie Walsh’s character would wind up with, despite an early test screening of the film showing an alternate romantic match for Ringwald’s Andie Walsh failing to win over fans.

7. Chasing Amy (1997)

Chasing Amy (1997)

For the power three presented in Kevin Smith’s critically acclaimed indie rom-drama Chasing Amy, the concept of codependent love and sexual fluidity inspire a genuine love triangle interpretation.

Ben Affleck impresses as a narrow-minded comic book writer alongside Jason Lee (My Name is Earl) and Joey Lauren Adams (who won a Golden Globe nomination for the film). For him, it’s hard to pick between his fiancée and his best buddy, but it’s much more difficult to choose between them.

8. Sabrina (1954)

The popularity of Sabrina’s love triangle plot device is largely due to its star billing, as was the case with The Philadelphia Story.

Humphrey Bogart and William Holden were both above-the-radar stars, but spectators were never quite sure which actor would land the role of the protagonist (Audrey Hepburn). This is something that the 1995 version by Sydney Pollack was unable to replicate.

9. Fight Club (1999)

Fight Club (1999)

Re-watchers of Fight Club should be able to readily accept the film’s irony (see: Tyler and Marla Singer’s jealousy of Tyler and Marla Singer).

The narrator (Edward Norton) only realizes that Tyler (Brad Pitt) and Marla (Helen Bonham Carter) were never romantically competing with each other. With no one else intervening, the walls come crashing down as he places his hand on hers. A love triangle detonated, igniting a blaze of charred remains.

10. The Graduate (1967)

Things changed drastically from where they started.

That The Graduate is consistently included in lists of the best films of all time is no accident. One might expect more of the same while evaluating love triangle films. In spite of the fact that Benajmin (Dustin Hoffman) pursued both Mrs. Robinson (Ann Bancroft) and Elaine (Katherine Ross) during the same Simon and Garfunkel-scored summer, it served as an intimate conflict that will be remembered for generations to come.