25 Essential Love Triangle Movies

For decades, we’ve seen love triangles as a recurring theme in both literature and film. There’s just something people enjoy about the entanglement of rivalry and romance. There are plenty – so it became difficult to narrow this list to just 25.

There are classics like Casablanca (1942) and its ever-so-quotable lines and Pillow Talk (1959) with its split-screen antics. New adaptations of period stories like Sense and Sensibility (1994) based on the novel by Jane Austen and The Other Boleyn Girl (2008) based on the Philippa Gregory novel about the life of Queen Anne and her sister Mary. Plus, there are some hits from the 80s and 90s, and some modern movies too.

So if you’re in the mood for a bit of smitten romance, here’s a list of 25 Essential Love Triangle Movies.

1. Molly Ringwald, Andrew McCarthy and Jon Cryer in Pretty in Pink (1986)

2. Humphrey Bogart, Ingrid Bergman and Paul Henreid in Casablanca (1942)

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

4. Sandra Bullock, Bill Pullman and Peter Gallagher in While You Were Sleeping (1995)

5. Keira Knightley, Andrew Lincoln and Chiwetel Ejiofor in Love Actually (2003)

6. Julia Roberts, Dermot Mulroney and Cameron Diaz in My Best Friend’s Wedding (1996)

7. Shirley MacLaine, Jack Lemmon and Fred MacMurray in The Apartment (1960)

8. Leonardo DiCaprio, Kate Winsley and Bill Zane in Titanic (1997)

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

10. Renée Zellweger, Colin Firth and Hugh Grant in Bridget Jones’s Diary (2001)

11. Alan Rickman, Kate Winslet and Greg Wise in Sense and Sensibility (1995)

12. Robin Wright, Cary Elwes and Chris Sarandon in The Princess Bride (1987)

13. Natalie Portman, Scarlett Johansson and Eric Bana in The Other Boleyn Girl (2008)

14. Jennifer Lawrence, Josh Hutcherson and Liam Hemsworth in The Hunger Games (2012)

15. Rock Hudson, Doris Day and Tony Randall in Pillow Talk (1959)

16. Adam Sandler, Drew Barrymore and Christine Taylor in The Wedding Singer (1998)

17. Clark Gable, Vivien Leigh and Leslie Howard in Gone with the Wind (1939)

18. Steve Carrell, Juliette Binoche and Dane Cook in Dan in Real Life (2007)

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

20. Nicolas Cage, Bridget Fonda and Rose Perez in It Could Happen to You (1994)

21. Paul Rudd, Reese Witherspoon and Owen Wilson in How Do You Know (2010)

22. Dustin Hoffman, Anne Bancroft and Katherine Rose in The Graduate (1967)

23. Kristen Stewart, Robert Pattinson and Taylor Lautner in Twilight (2008)

24. Ryan Gosling, Rachel McAdams and James Marsden in The Notebook (2004)

25. Steve Martin, Goldie Hawn and Dana Delany in Housesitter (1992)

What’s your favorite on-screen love triangle?

Meredith is Associate Creative Director at Half Price Books Corporate.
You can follow her on Twitter at @msquare21.

4 thoughts on “25 Essential Love Triangle Movies

  1. No Shakespeare?! Whether you love drama or comedy, there's a love triangle for you… and well done movie! Check out Midsummer Night's Dream, Much Ado About Nothing, and Twelvth Night. There's also the tribute movie Shakespeare In Love. You also neglected Swet Home Alabama, Serendipity, and The Cutting Eddge. Glad to see you included Bridget Jones' Diary. 🙂

  2. I think, technically, that The Wedding Singer is more like a love square if they really wanna bring in Julia's cousin….Julia, Glen, Robbie, Julia's cousin….and at that they only went on one date….so I wouldn't include her anyway.

  3. Pingback: 30 Film Score Favorites | The Half Price Blog

  4. Pingback: 10 Unforgettable, Quotable Lines from Casablanca | The Half Price Blog

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