Romantic comedies are usually escapist fantasies, allowing the audience to imagine themselves being swept off their feet by the perfect meet-cute, the ideal first date, or some over-the-top profession of true love. Most of the time these movies consist of the romantic leads encountering a series of increasingly elaborate and preposterous obstacles to their perfect union. However, the audience can rest easy in the knowledge that, no matter how bad it gets, the two heroes will find a way to get together by the end.
But real life is complicated, and sometimes things don’t go to plan. Some of the most powerful romances are those they don’t last. They are fleeting, ephemeral, doomed romances that teach profound lessons about life and love.
10 Pretty in Pink (1986)
Pretty in Pink is one of the defining teen rom-coms of the '80s. The plot centers on high school senior Andie Walsh (Molly Ringwald), who lives with her father in a working-class neighborhood in Chicago. Her best friend Duckie (Jon Cryer) is secretly in love with her, but Andie wants to go to the prom with rich kid Blane (Andrew McCarthy).
In the original script, the film ended with Andie and Duckie getting together, but this was changed to Blane at the last minute. At the time, the filmmakers were worried the original ending might come across as classist for implying those from working-class backgrounds and the more wealthy shouldn’t fraternize. But the revised ending also holds up better by today’s standards, as it doesn’t reward Duckie for some of his more obsessive behavior towards Andie.
9 Drinking Buddies (2013)
Joe Swanberg’s rom-com Drinking Buddies stars Olivia Wilde and Jake Johnson as two friends who work at a craft beer brewery in Chicago. Although they seem like they would make the perfect couple, both are already in relationships. Over the course of the film, the two explore their potential feelings, but ultimately realize that they probably aren’t meant to be together.
While it’s a pretty straightforward story, the film’s lo-fi indie sensibilities, heightened by the fact that most of the dialogue was improvised, makes its explorations of human relationships feel real and genuine.
8 La La Land (2016)
A critical darling and box office success, modern musical rom-com La La Land follows struggling jazz pianist Sebastian (Ryan Gosling) and aspiring actress Mia (Emma Stone) as they both attempt to find fame and fortune in LA’s often fickle entertainment scene.
Surprisingly, the film ends with the two romantic leads parting ways to pursue their individual dreams: Mia becomes a famous actress, while Sebastian opens his own jazz club. In the film’s final moments, the audience gets a bittersweet dream-montage of how Mia’s and Sebastien’s lives could have played out if they had chosen to stay together. But ultimately the true ending feels more in tune with their bohemian characters, with both deciding to pursue their artistry instead of their relationship.
7 (500) Days of Summer (2009)
Surprise indie hit (500) Days of Summer stars Joseph Gordon-Levitt as Tom, a hopeless romantic who falls for Summer (Zooey Deschanel). The film plays out non-chronologically, as Tom reflects on some of the key moments in their failed relationship.
More a coming-of-age story than a true romance, the great thing about the film – and the aspect that elevates it over similar, though more indulgent, indie rom-coms like Garden State (2004) – is that it actively plays with the manic pixie dream girl trope. For Tom, Summer is an idea, rather than a real person, and it is ultimately his inability to humanize her that dooms their relationship.
6 Chasing Amy (1997)
Writer and director Kevin Smith’s late-'90s cult favorite Chasing Amy stars Ben Affleck as Holden, a comic book artist who falls in love with fellow artist Alyssa (Joey Lauren Adams). Holden soon discovers that Alyssa is gay, but he pursues a relationship with her anyway. Ultimately, it is Holden’s inability to deal with Alyssa’s sexually adventurous past that dooms whatever small chance they had to be together.
While there are some predictably problematic jokes in there, Chasing Amy is in many ways quite a progressive film that explores sexual identity in a surprisingly humanistic way. Kevin Smith based many of the characters and events depicted in the film on his own lived experiences, which imbues it with a sense of realism and turns what could have been another forgettable raunchy sex comedy into a sweet and enduring hit.
5 Ghost World (2001)
Black comedy Ghost World is a bit of genre mashup: part art film, part adolescent coming-of-age drama, part odd romance. The film follows the everyday adventures of two friends, Enid (Thora Birch) and Rebecca (Scarlett Johansson) in the summer after they graduate from high school. After the girls find a personal ad posted by a lonely middle-aged man named Seymour (Steve Buscemi), Enid strikes up an unlikely friendship with him, which seems like it might develop into something more romantic.
The film is by turns acerbically witty and poignant, exploring ideas around the loss of youth and innocence while maintaining its deadpan humor throughout. But the great strength of the film is its wryly observed characters, who come across as real, intelligent, flawed human beings.
4 Lost in Translation (2003)
Sofia Coppola’s breakout hit Lost in Translation stars Scarlett Johansson and Bill Murray as two lost souls who meet in a hotel in Tokyo. Bill Murray plays Bob Harris, an aging movie star who has been flown to Japan to film a whiskey commercial, while Scarlett Johansson plays listless Charlotte, who is accompanying her celebrity photographer husband (Giovanni Ribisi) while he is on assignment in Tokyo. Both characters suffer from insomnia, and they form an unlikely – and potentially romantic – bond over late-night drinks in the hotel’s bar.
As with many of Coppola’s films, Lost in Translation has a dreamlike quality. The film’s many long, lingering shots give the impression it is capturing something fleeting and ephemeral: this impossible, bittersweet connection that exists between these two semi-tragic characters.
3 My Best Friend’s Wedding (1997)
Julia Roberts' vehicle My Best Friend’s Wedding was a box office hit and remains one of the most loved '90s rom-coms. When New York food critic Julianne Potter (Roberts) finds out lifelong friend Michael O’Neal (Dermot Mulroney) is getting married to young college student Kimmy Wallace (Cameron Diaz), she travels to Chicago to sabotage the wedding and profess her love to Michael.
Featuring a charming lead performance from Roberts, My Best Friend’s Wedding is a perfect rom-com; made even better by the fact that it subverts the typical happy-ever-after-ending in favor of something more true to life.
2 Celeste and Jesse Forever (2012)
Underrated indie rom-com Celeste and Jesse Forever stars Rashida Jones and Andy Samberg as the eponymous Celeste and Jesse, two high school sweethearts who are now in their early 30s and have decided to get a divorce.
The film explores the ways in which relationships change over time. Although it’s clear that there is still a lot of chemistry between them – and they seem close to reuniting on a number of occasions – the film ends with them each going their separate ways: Jesse has matured and is fathering a child with another woman, while Celeste is beginning to date other people.
1 Annie Hall (1977)
Woody Allen’s classic romantic comedy focuses on neurotic New York comedian Alvy Singer (played by Allen) who is reflecting on his failed relationship with the titular Annie Hall (Diane Keaton). The film is a melancholic but often hilarious meditation on love and relationships, peppered with fourth-wall-breaking moments and surreal interludes – such as when the movie momentarily turns into a Disney cartoon.
And yet, despite all these strange comic sequences, the end result is a movie that is far more serious in tone than Allen’s earlier farcical comedies. Notable for its strong characterization, clever script, and insights into love and the human condition, Annie Hall was a worthy winner of that year’s Academy Award for Best Picture.
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