The romantic comedy genre has a history so long and vast, that it has been around in cinema pretty much since its inception. As such, numerous rom-coms have been made over the years which go down in history as some of the most memorable and popular movies ever made.
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These kinds of films can be as hilarious as they can be tender and sweet, a phenomenal combination that ensures they'll stay on audiences' minds for years to come. From Roman Holiday to Annie Hall, these are classics that have aged like fine wine.
1 Not Your Typical Shakespeare Adaptation — '10 Things I Hate About You' (1999)
Cleverly bringing Shakespeare's old classic The Taming of the Shrew to the modern setting of an American high school, 10 Things I Hate About You is one of the most fun and endearing teen rom-coms to come out of the '90s.
The movie features one of Heath Ledger's most charming performances and a few of what have already become some of the most iconic scenes in the genre. Ironically, it's a movie that's pretty much impossible to hate, leading it to become a modern classic and a standard of quality for teen movies.
2 A Neverending Loop of Joy — 'Groundhog Day' (1993)
Throughout the years, the time travel genre and the rom-com have proved to get along pretty well. Perhaps the most popular mixture of these two kinds of stories is Groundhog Day, where Bill Murray plays a narcissistic TV weatherman who finds himself repeating the same day over and over again.
The movie is a bundle of joy, kindness, and character growth packed into a breezy 100 minutes of laughs and romance. If you like time travel stories, funny stories, and romantic stories, it's impossible for you to not love Groundhog Day, even if you think you don't like rom-coms.
3 When Audiences Met Laughter — 'When Harry Met Sally...' (1989)
In When Harry Met Sally..., two friends discuss whether sex ruins a friendship between a man and a woman. Eleven years pass, and they're still a long way away from finding the answer.
On top of two iconic performances from Billy Crystal and Meg Ryan, it isn't hard to see what has made this movie age so terrifically well. The two main characters have amazing chemistry, all the jokes land, the dialogue is marvelously written, and the whole thing balances humor and sweetness better than most other rom-coms before or since.
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4 A Movie About a Nervous Romance — 'Annie Hall' (1977)
Woody Allen's Annie Hall is the movie that took the Best Picture Oscar home on the same year that Star Wars was nominated. And, to be frank, it absolutely deserved it, and it's just as memorable a film.
Semi-autobiographical and incredibly witty, this is undoubtedly one of the most intelligently written romcoms ever made. Allen's magnum opus constantly pushes the limits of the genre and the medium itself, delivering a final product that's hilarious, relatable, and earnest.
5 An Incredible Experience, Movie-Wise — 'The Apartment' (1960)
Writer-director Billy Wilder was one of cinema's greatest masters of the rom-com, and he proved it with his Oscar-winning masterpiece The Apartment, about a man climbing the corporate ladder through lending his apartment to executives for them to see their mistresses.
The Apartment is a true marvel of cinema. Visually impressive, beautifully directed, cleverly written, and with an incredible cast of actors at the top of their game, it's no wonder why it's still one of the paragons in the genre.
6 Well, No Movie's Perfect. But This One Comes Close — 'Some Like It Hot' (1959)
Another Billy Wilder comedic masterpiece, Some Like It Hot is the story of two musicians who witness a mob hit, and have to join an all-girl band disguised as women in order to escape the gangsters.
This is one of those movies were the premise is a delight in itself, and all the ingredients miraculously manage to elevate it into something beyond special. In many ways, Some Like It Hot was way ahead of its time, and for decades it has continued to delight and comfort audiences in search of some laughs and some romance.
7 Romance In Romantic Rome — 'Roman Holiday' (1953)
In this touching, beautifully shot classic, a touring European princess takes off for a night while in Rome, where she meets an American reporter who bets his editor he can get an exclusive interview with the royal.
Helmed by the charisma of two of the most charming actors in Hollywood's history, Audrey Hepburn and Gregory Peck, Roman Holiday is humor and romance that can soften even the coldest and hardest hearts. Simple and uplifting, it's the perfect film to watch if you're looking for something airy and easy to enjoy.
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8 What a Glorious Feeling Indeed — 'Singin' in the Rain' (1952)
Singin' in the Rain is as much of a love letter to the magic of movies as it is a love letter to the magic of living, loving, laughing, dancing, and singing. If you're feeling under the weather, this movie is guaranteed to make you feel better.
Full of catchy songs, hilarious jokes, and emotional scenes, Singin' in the Rain is a movie that's practically impossible to dislike. It beautifully pays homage to cinema's transition to talkies, while telling a sweet story about love and how it can triumph in the Hollywood system.
9 The Definitive Movie Rom-Com — 'It Happened One Night' (1934)
In the rom-com movie genre, there's a before It Happened One Night and an after It Happened One Night. It's astonishing that over 80 years later, it's still lauded as one of the best movies ever made.
The film was incredibly popular at the time, becoming the first movie to win all five major Oscars (a feat only achieved by it, One Flew Over the Cuckoo's Nest, and The Silence of the Lambs). Thankfully, it has proved to be totally timeless. The actors do an amazing job, the jokes are still genuinely laugh-out-loud funny, and the romance element works perfectly.
10 No One Does It Like Chaplin — 'City Lights' (1931)
Charles Chaplin was arguably cinema's greatest slapstick comedian ever, and his films often delved into romance as well. He made many of the funniest and sweetest rom-coms of the silent era, and City Lights is perhaps the best of them all.
The movie is a masterclass in storytelling without the need for spoken words. The story it tells is beautiful and deeply moving, even poignant at times, and always an absolute delight to watch unfold. If you've never watched a Chaplin movie (and you absolutely should), City Lights is the perfect place to start.
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