The basic rule of good romantic stories is that the main heroes will end up together. They might have to face many ordeals before they can get their happy ending. However, these ordeals usually serve to bring the heroes together, even closer. The final idyllic ending gives hope not just to the characters but to the audience as well.
Then there are those movies that turn the genre conventions upside down. In many ways, they tend to be much more realistic. They show that relationships don’t always work out and that it’s normal to break up with someone and start anew. Some romantic comedies play with other genres and they also introduce the thought that failed romance isn’t the end of the world.
10 Annie Hall (1977)
A lot of Woody Allen’s films don’t end with the couple staying together. However, one of his most famous films that follow this pattern is Annie Hall. The film stars Allen himself, and his long-time friend and one-time girlfriend, Diane Keaton. The film’s humor is intelligent, full of quips and long conversations. Diane Keaton has become a fashion icon thanks to this role, and viewers might be interested to hear it was based on real-life events.
9 The Purple Rose Of Cairo (1985)
Mia Farrow has portrayed many great roles, but The Purple Rose of Cairo is one of her most original movies. Farrow played shy woman Cecilia, who lives in an unhappy marriage. Her only joy is going to the movies. One day, the protagonist of the movie she watches steps out of the film and goes to her. The film is full of bittersweet and funny moments. It can’t have a happy ending, though, since the love between real life and fiction rarely ever ends well.
8 Ghost (1990)
Ghost isn’t a typical romantic film because its male protagonist is dead, a ghost, for most of the time. It isn’t a typical comedy either because even though it has a lot of hilarious moments, its heroes are in danger. However, Ghost still belongs among one of the best films where the characters don’t end up together. Before they separate forever, they at least get to share one last kiss, for all it’s worth.
7 My Best Friend’s Wedding (1997)
Julia Roberts was the queen of romantic comedies in the 1990s. My Best Friend’s Wedding is an undeniable classic. Roberts plays Julianne, a New York food critic, who decides to stop her best friend Michael’s wedding when she learns he’s getting married. Needless to say, things don’t go according to plan.
Nowadays, many romantic comedies subvert the genre’s expectations, but back in the 1990s, it wasn’t as common yet. That’s only one of the reasons why this film became so popular among audiences.
6 Shakespeare In Love (1998)
The Academy Award-winning film, Shakespeare In Love, isn’t a typical romantic comedy. For one, it takes place in the late 16th century, and it also tells the story of people who truly lived. William Shakespeare, a talented poet and playwright, struggles with writer’s block. His luck changes when he meets his new muse, Viola de Lesseps. The only problem is that Viola is engaged to be married. The film works with masks and mistaken identities and has a lot of funny moments.
5 Easy Virtue (2008)
When a young Englishman, John, marries a free-spirited American woman, Larita, his family is horrified, especially his mother and sisters, in Easy Virtue. They hate everything about Larita, from her behavior to the fact she’d been married before and got divorced. Luckily, Larita finds understanding in someone else. The film is full of dark British humor, starring excellent actors such as Jessica Biel, Colin Firth, or Kristin Scott Thomas. It makes fun of the differences between British people and American people in the best way possible.
4 500 Days Of Summer (2009)
500 Days of Summer shows that relationships can be good even if they don’t lead to happily-ever-after. Joseph Gordon-Levitt plays Tom, a man who falls hopelessly for Zooey Deschanel’s Summer. The film isn’t as hilarious as some others on this list but still has enough funny moments to rank as comedy.
What makes it different is that the story doesn’t run chronologically as Tom recalls his relationship with Summer once it ended.
3 La La Land (2016)
Also not a typical rom-com, La La Land combines multiple genres, including romance, drama, comedy, and musical. Taking place in Hollywood, the land of dreams, the film tells the story of two people whose ambitions drive them apart, but their relationship was sweet while it lasted. Emma Stone and Ryan Gosling shine as the main duo.
2 When We First Met (2018)
Some of the best rom-coms use fantasy or sci-fi elements to spice up the plot. When We First Met is a good example of that. Noah (Adam Devine) met the perfect girl, Avery (Alexandra Daddario), three years ago. He got friend-zoned, and now Avery has a serious boyfriend. Luckily for Noah, he travels back in time and ends up experiencing their first meeting over and over again, stuck in a time loop. The film is full of hilarious moments as Noah tries to set himself up with Avery and fails spectacularly. In the end, it also shows that some relationships aren’t meant to be, but they can open the door to something better.
1 Last Christmas (2019)
Emilia Clarke often plays characters who undergo a traumatic experience. Her character, Kate, in Last Christmas, fits the bill. She doesn’t get along with her family, she’s lonely, and she has a strange job. Kate meets a nice guy, Tom (Henry Golding), and she gradually learns how to live again. Last Christmas is the perfect Christmas movie, it combines romance, comedy, and a bit of magic.
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