In honor of Noah Baumbach’s new film Challengers, which focuses on the intersecting love lives of three tennis players, we are taking a look at some of the best love triangle movies. The 31 films included on this list span decades, genres, and romantic situations that may end up convincing you that, when it comes to love, three is a crowd. (There’s even one four-way love square, which is said to be the most tragic romance on this list.)
The greatest love triangles include a martial arts epic in which two men become rivals for a woman’s heart and a Jane Austen-inspired melodrama. John Hughes created an unrequited love triumvirate for the teen set, while basketball becomes the third wheel in Spike Lee’s full length directorial debut.
From a movie that casts Hugh Grant as the villain to a pair of Woody Allen films with troubled romances and a notable soundtrack, below are the best love triangles that Hollywood has to offer.
The Notebook (2004)
In the 1940s-set movie, Allie (Rachel McAdams) must choose between her fiancé Lon (James Marsden), a caring and gentle World War II veteran who she helped nurse back to health, or her first love Noah (Ryan Gosling), a hotheaded carpenter who drives her nuts, but forces her outside her comfort zone. What makes the romance, based on the Nicholas Sparks novel of the same name, so compelling is that even those who are happy to see her end up with Noah can’t help but hope that Lon finds his own happily ever after.
Broadcast News (1987)
The blonde-haired blue-eyed Tom (William Hurt) is a natural, while Aaron (Albert Brooks) is not quite safe (and predictable) for TV. Despite their professional differences, both men are competing for the affections of the same woman: a skilled but sometimes severe news producer, Jane (Holly Hunter). The ending of Broadcast News, which feels rather ahead of its time, shows that there are far more than two choices when it comes to both the news business and matters of the heart.
The Graduate (1967)
The Graduate begins with the seduction of recent college grad Benjamin (Dustin Hoffman) by Mrs. Robinson (Anne Bancroft), the wife of his father’s law partner who is at least 20 years his senior. (In real life, the 35-year-old Bancroft was only six years older than her co-star.) The Mike Nichols comedy is all fun and late night liaisons, until Benjamin finds himself falling for her more age appropriate daughter, Elaine (Katharine Ross), much to Mrs. Robinson’s chagrin. The film’s memorable final shot will leave you wondering whether it was about love or revenge.
Bridget Jones’s Diary (2001)
In the movie Bridget Jones’s Diary, perpetual singleton Bridget Jones (Renée Zellweger) finds herself caught between her womanizing boss, the Mr. Wickham-esque Daniel (Hugh Grant at his absolute smarmiest) and the reindeer jumper-wearing barrister Mark Darcy (Colin Firth), who, as his name suggests, is as hard to read as Jane Austen’s romantic hero (whom the actor once portrayed). It’s only after getting to know each of them better (and embarrassing herself) that Bridget realizes, just like Elizabeth Bennet, she is meant to be with Mr. Darcy.
Casablanca (1942)
might have the most iconic love triangle in cinematic history. Amid World War II, exiled former American freedom fighter Rick Blaine (Humphrey Bogart) has built a life for himself in the titular Moroccan city, far away from Ilsa (Ingrid Bergman), the woman who abandoned him years earlier. But when she unwittingly walks into his gin joint with her husband, Czech resistance leader Victor Lazlo (Paul Henreid), looking for a way to escape the Nazis, it’s clear things aren’t quite over between them. Yet Rick knows that the only way to save her is to let her go. They may not have a future together, but they’ll always have Paris —and for him, that has to be enough.
The Age of Innocence (1993)
Grab all of the tissues, you’re going to need them for the Martin Scorsese-directed Gilded Age weepie based on Edith Wharton’s 1920 novel of the same name. In 1870s New York, Daniel Day Lewis’ chivalrous lawyer Newland Archer is set to marry a respectable woman, the sweet and virtuous May Weiland (Winona Ryder). But he soon finds himself falling in love with May’s cousin, Countess Ellen Olenska (Michelle Pfeiffer), who has been ostracized by the city’s elite following her separation from her husband. Age of Innocence is a beautiful tragedy of manners that questions whether it is better to follow one’s own heart or the rules set by polite society.
The Philadelphia Story (1940)
If you were Katharine Hepburn, who would you rather marry: Cary Grant or Jimmy Stewart? It’s the question at the heart of the classic romantic comedy The Philadelphia Story. Wealthy socialite Tracy Lord (Hepburn) is on the verge of marrying stuffy fiancé George Kittredge (John Howard), when her ex-husband C. K. Dexter Haven (Cary Grant) and a handsome reporter Mike Connor (Jimmy Stewart) turn up to disrupt her plans.