The 50 Greatest Romantic Comedies of All Time (10-1)

Charles Chaplin once said that he needed three ingredients to make a successful comedy (a man, a policeman, and a pretty girl), two for a love story (a man and pretty girl) but only one for a drama (a man without a pretty girl or alternatively, a girl without the pretty) and yet even he, with his rock solid formula, couldn’t crack the romantic comedy. Even though it’s the genre that’s the most dependent on cliches and tropes, it’s easily the hardest to get right. The alchemy behind a successful ‘chick flick’ is nearly impossible to get right. Since what people find funny and what people find romantic are entirely subjective, melding the two can be a tricky proposition. But it can and has been done. In honor of Valentine’s Day, Romona Comet and Sailor Monsoon have compiled a list of what they think best represent the genre. The films that make you laugh, that make you cry and more importantly, make you believe in the power of love. 

This is The 50 Greatest Romantic Comedies of all Time.

10. The Proposal (2009)

When she learns she’s in danger of being deported due to an expired visa, an overbearing book editor (Sandra Bullock) forces her put-upon assistant (Ryan Reynolds) to marry her. In the Crazy, Stupid, Love write up, I mentioned that the two Ryans (that being Gosling and Reynolds respectively) are the kings of the chick flick but what I failed to mention, is that Bullock is the queen. I know no actor wants to be typecast and I understand their need to do new things, to challenge themselves with new roles but Sandie needs to stop fucking around and stick to rom-coms because A) the genre desperately needs her and B) she’s extremely hit or miss in everything else.

That sentiment can also be applied to Reynolds. They’re two actors who are at their best in lovey-dovey, predictable fluff, with The Proposal being among the best of their respective careers. Not in terms of its storytelling or on its technical merits but by the simple virtue of the fact that they’re both in it together. Their chemistry is off the charts and easily outweighs any flaw and casts an enormous shadow over everything else. The two of them together is the movie. The king and queen of the romantic comedy have graced us with but one collaboration and luckily it’s a winner.

[Sailor Monsoon]

09. It Happened One Night (1934)

Every romantic comedy, whether intentional or not, is stealing from It Happened One Night. This is it, this is the progenitor of every trope and cliche you either love or hate. That isn’t to say that it’s the first movie to add laughs to a love story or that it created said tropes and cliches but it most definitely popularized it and by extension, the overused narrative stereotypes that are associated with them. Capra’s timeless classic about a bullheaded reporter (Clark Gable) and a spoiled heiress (Claudette Colbert) who, at first, hate each other but then fall in love, is a perfectly constructed story that has been remade a million times without ever being officially remade. All roads lead back to this film. Even fucking Bugs Bunny for chrissakes.

[Sailor Monsoon]

08. While You Were Sleeping (1995)

This has been one of my favorite romantic comedies since it was released in theaters in 1995. Sandra Bullock slipped seamlessly into the role first offered to Julia Roberts and the film catapulted her to stardom. While the premise itself was a bit improbable, the cast (specifically Bullock) and Jon Turteltaub’s direction somehow manages to make it work.

Lucy is not your typical rom-com beauty queen (nor does she have to undergo some magical transformation from drab to fab in order to win her man) and she never has to change who she is in order for Jack (Bill Pullman), or Peter (Peter Gallagher) for that matter, to fall in love with her. She’s awkward, kind and relatable on every level while Jack and Peter could not be more different, Peter being a wealthy, self-absorbed attorney and Jack a blue-collar boy next door who likes to build furniture.

Jack and Lucy’s chemistry is really what makes this movie work. There aren’t many rom-com tropes here. They’re not bitter enemies fighting attraction. They’re not forced together in contrived situations. Their interactions are natural despite the unusual circumstances and even once you realize they’ve fallen in love over the course of what is essentially a week, you still believe it. What more could you want from a rom-com?

[Romona Comet]

07. Man Up (2015)

While on her way to her parents’ 40th wedding anniversary, a somewhat aimless, cynical woman named Nancy finds herself sitting with a chirpy optimist who is reading a book called 6 Billion People and You. After a rude confrontation, Nancy falls asleep and when she wakes, she finds the woman left her a copy of the book, opened up to a chapter titled Your Negative Thoughts are Ruining Your Life (and Everyone Else’s…). Irritated, Nancy leaves the train to find the woman and return the book, but she is quickly mistaken by a man named Jack to be his blind date. Rather than correct him, Nancy decides to pretend to be who he thinks she is, and the two embark on a rather eventful evening of lies, honesty, and ex-lovers.

Lake Bell and Simon Pegg are perfectly matched here, breathing life into two characters who feel so refreshingly removed from the classic rom-com archetypes. Their goofy, yet sexy, chemistry is such a joy to watch that it’s easy to ignore the film’s (few) flaws. Man Up doesn’t try to reinvent the genre, but it does a darn good job at giving it something new with its low key charm and hilariously honest take on dating in the modern world.

[Romona Comet]

06. The Big Sick (2017)

Based on the incredible true story of how Kumail Nanjiani met his real-life partner, The Big Sick tells the story of a Pakistan-born comedian (Nanjiani) and a grad student named Emily (Zoe Kazan) who fall in love but due to a clash of cultures, the couple breaks up. But when Emily contracts a mysterious illness, Kumail finds himself forced to face her parents (who aren’t exactly thrilled to be hanging out with the man who broke their daughter’s heart) his family’s expectations, and his true feelings.

One of the film’s biggest strengths, apart from the excellent cast and hilarious writing, is the fact that it deals with a side of love few films hardly ever address. Which is that it’s hard. True love is hard work. To get that storybook happily ever after, you gotta work at it. You can’t just cut and run when shit gets difficult and that’s the film’s ultimate message. Fight for love.

[Sailor Monsoon]

05. The Philadelphia Story (1940)

When a rich woman’s (Katharine Hepburn) ex-husband (Cary Grant) and a tabloid-type reporter (Jimmy Stewart) turn up just before her planned remarriage, she begins to have doubts about the marriage. Has the presence of her ex stirred up old feelings or is she falling for the reporter without even knowing it? The Philadelphia Story is utterly delightful from start to finish, with everyone involved working on peak form. Hepburn and Grant still have that red hot chemistry they had in their previous film Bringing Up Baby and while Stewart may think his Oscar win was undeserved, he’s as charming here as he’s ever been. A great storyline, an excellent cast and a razor-sharp script (ain’t nothing better than great old-timey dialogue) made this film an undisputed classic of the genre.

[Sailor Monsoon]

04. The Princess Bride (1987)

The only reason this isn’t number 1, is the fact that it’s kinda technically not a romantic comedy. If we were judging these films on merit alone, The Princess Bride would’ve won hands down. This is easily the best film on this list and it’s not even close. No offense to the other films on this list but if we’re to take this film and the number 1 film and put them in a race, that film would be Usain Bolt and this would be a rocket-powered Ferrari. That’s how huge the disparity in quality there is between this film and everything else but again, this isn’t a “romantic comedy” per se, so we decided it couldn’t be any higher than number 5.

When people compare Star Wars to other films, they tend to compare it to other big franchises such as the Lord of the Rings trilogy or the Harry Potter movies but I think the only film that can and has rivaled it in terms of popularity and adoration, is The Princess Bride. It’s easily as quotable, has just as many great scenes and characters and both have a timeless feel to them that few films can replicate but what this film has that Star Wars doesn’t, is an amazing love story. This is the Star Wars of love stories.

[Sailor Monsoon]

03. The Before Trilogy (1995-2013)

As ambitious as Boyhood but nowhere near as insufferable, the Before Trilogy told one long romance over the course of thirty years. Linklater spaced out each entry about ten years apart to let time do the heavy lifting for him. Jesse and Celine (played by Ethan Hawke and Julie Delpy, respectively) first crossed paths in Before Sunrise and fell madly in love but since both were young twentysomethings, they both decided to choose life over love. Ten years later, the two lovers cross paths again in Before Sunset and now that they’re older and perhaps wiser, they finally decided to give their story the “happily ever after” it deserves. We catch up with them ten years after that in Before Midnight to see where their love has taken them.

Each entry works on its own but taken on the whole, each film acts as the beginning, middle and end of a perfect love story. The Sunrise Trilogy is more than just a story of two people in love, it’s a thorough examination of love itself. Why we can’t choose who we love, why time is, unfortunately, more important than compatibility and how amazing it feels to be loved and in love. The thirty-year saga of Jesse and Celine is the ultimate love story.

[Sailor Monsoon]

02. Sleepless in Seattle (1993)

It isn’t a coincidence that Ryan’s character (and the film for that matter) spends a good chunk of screen time watching and rewatching An Affair to Remember, it’s a not so subtle trick on the part of the movie to let the audience know that it’s a sappy 1950s tearjerker masquerading as a 1980s love story and the reason it wants you to know this, is that it doesn’t care that you know. This is an unapologetic throwback to the types of films Hollywood doesn’t make anymore. The Lubitsch-Wilder-Capra movies of yesterday, where all you needed was a likable male lead, a lovesick female and some chemistry.

This adheres so strictly to the formula, that it’s in danger of self-parody but because the film has so much sincerity and heart, you completely buy into it. Because it’s so saccharine sweet, It’s become the target of a dozen parodies but all that did was reinforce the film’s enduring legacy. No amount of ridicule or mockery can tarnish it, it is stronger than a thousand Mad magazine jokes. While Romona and I both thought the number 1 was more deserving of the title of Greatest Romantic Comedy of all Time, Sleepless in Seattle is probably the one I think of when I think of romantic comedies. Between the two, this one is probably the definitive rom-com.

[Sailor Monsoon]

01. When Harry Met Sally… (1989)

The ‘opposites attract’ trope is a successful one, but boy, do you need the right characters, and actors, to pull it off. Meg Ryan and Billy Crystal’s chemistry is insanely strong. It helps that Harry and Sally as characters are fully fleshed out. They are flawed. They are both charming and confident at times, frustrating and insecure at others. They feel real, and that’s the mark of a really good romantic comedy.

I rooted for the ending I received, but the honest to God truth is, I would have been okay with it if they had remained friends, it was just that good. As a bonus, along the way we get to see their best friends Marie (Carrie Fisher) and Jess (Bruno Kirby) fall in love and deal with their own relationship problems, which provides its own brand of comic relief in the midst of Sally and Harry’s angst.

One of my favorite parts of the movie is the occasional break where older couples are interviewed and tell us how they met and knew they had found the one. The couples may be portrayed by actors, but the stories themselves are true and I am not ashamed to admit I cried through all of them.

When Harry Met Sally continues to be the standard by which so many modern rom-coms are graded, and it’s disappointing how few even come close.

[Romona Comet]

20-11 | Fall in Love Again?

What did you think of the selection? Were there any rom-coms that you thought should have made the list? Let us know in the comments below!


Author: Romona Comet

"I'm probably watching a rom-com right now."