The 50 Greatest Romantic Comedies of All Time (40-31)

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.

40. What If (2013)

With his ten year Harry Potter career behind him, it’s been quite the adventure watching what Daniel Radcliffe does next. His choices have been rather quickly, and at times, questionable, but it’s hard to deny they’ve always been interesting. So it was a bit of a surprise when he waded into the not so deep waters of the rom-com genre. What was surprising was that Radcliffe managed to avoid a stale, formulaic production, opting for the low budget indie romance, What If. Radcliffe stars as Wallace, a medical school drop out who experiences a near perfect meet-cute moment with animator Chantry, played by the ever reliable Zoe Kazan.

Unfortunately for Wallace, Chantry has a long-time boyfriend, and the two eventually grow to become best friends. Their path to a potential happily ever after takes much longer than either would probably like, but it’s so worth the journey. Radcliffe and Kazan boast some undeniable chemistry and the film itself stays true to its rom-com roots while successfully breaking free of the tired and expected cliches. What If is both funny and romantic, fueled by relatable leads and fantastic supporting turns by Adam Driver and Mackenzie Davis. It’s near impossible to replicate the charm and romance that made When Harry Met Sally such a classic, but What If could be considered a worthy successor.

Romona Comet

39. Sleeping with Other People (2015)

Lainey and Jake lost their virginities to one another in college, and when they meet up again years later, they’re both damaged people, addicted to one night stands and toxic relationships. But they find some sense of normalcy with one another, and they remain determined to stay friends while leaving sex out of the equation, aware that acting on their attraction will destroy the connection they’ve made together.

There are some movies that when you begin to watch, you know exactly what you’re going to get. That can be said for most in the rom-com genre, but Sleeping With Other People was truly a pleasant surprise. Yes, it’s yet another romance surrounding two very attractive friends, and there are plenty of rom-com tropes to be had, including the expected, albeit frustrating, conversation to discuss whether or not men and women can just be friends. Thankfully a strong, witty script from Leslye Headland and incredible chemistry between Jason Sudeikis and Alison Brie keeps Sleeping With Other People afloat amidst some of the more formulaic aspects of the movie.

Romona Comet

38. My Best Friend’s Wedding (1997)

Having watched this movie several times over the past two decades, I still appreciate its deviation from the typical rom-com formula. Julia Roberts as Jules is our leading lady, but she’s not exactly one we want to root for. Her devious machinations are born out of jealousy, but does she really love Michael? As her editor and friend George (a very charming Rupert Everett) asks, “do you really love him, or is this about winning?”. We always want what we can’t have, and Jules clearly has trouble distinguishing love from love. Perhaps she’s just afraid of having to share him with another woman, when she’s been the woman in his life for the past nine years. 

Roberts perfectly balances her role, keeping Jules from becoming a complete villain in the story because, despite some truly awful behavior, Jules is also able to recognize right from wrong, even if she attempts to justify the wrong. With a little help from George, who essentially plays her conscience, you know she’s going to do the right thing in the end.

Romona Comet

37. Two Weeks Notice (2002)

Two Weeks Notice tells a story that has been told a thousand times over. An opposites-attract love story that finds the intelligent, serious heroine falling for the wealthy, shallow man-child and vice versa. She needs to learn to let loose and enjoy life, he needs to learn to grow up and be the man she knows he can be. I’m not sure how well the movie would work without the comedic talents of Bullock and Grant. The case could be presented for them being rom-com royalty, and it baffles me that this is the only film they’ve ever starred in together.

Two Weeks Notice is predictable fluff, but Grant and Bullock deliver enough humor and chemistry to make it worthwhile predictable fluff. I’m a sucker for the grand gesture scene, and Two Weeks Notice has one of my favorites.

Romona Comet

36. Scott Pilgrim vs the World (2010)

Although it’s based on a series of graphic novels, Scott Pilgrim vs the World is the closest we have to a live action video game. And it’s not just the copious amounts of game related references, easter eggs or in-jokes either. The film has the structure and style of a game. Filled with non-stop energy and with more edits than a Michael Bay film, Scott Pilgrim might be the fastest film in existence. Directed as though Wright was being chased, this puppy starts at 100 mph and never slows down for a second. It’s visually inventive, rip-roaringly funny and loaded with first class performances. It’s a near perfect adaptation in that it changes somethings from the books, omits others (poor Kim got the shaft) and moves things around, to provide an equally as good experience for fans of the comic. And sweet baby Jesus, does that soundtrack slap.

Sailor Monsoon

35. Love, Simon (2018)

Love, Simon’s tagline is “everyone deserves a great love story.” And that certainly includes the LGBTQ community. Simon (Nick Robinson) is a gay teen who has yet to come out to his friends and family. He strikes up a pseudo-relationship with an anonymous classmate online nicknamed “Blue”. While Simon speculates about who Blue could be, another classmate discovers Simon and Blue’s intimate correspondence and blackmails Simon into helping him hook up with Simon’s friend, Abby. From there, things only get more complicated for Simon, who is forced to come out on someone else’s terms. 

This is a teenage romantic comedy done right. It’s heartfelt and emotional, and has so many shades of John Hughes while being considerably less problematic. I remember seeing this movie with someone who had yet to come out, and later I realized just how important the movie was to them, seeing themselves represented on screen as so much more than just a rom-com stereotype. Love, Simon is an inspiring love story for a new generation with a message that absolutely deserves to be heard.

Romona Comet

34. The Shop Around a Corner (1940)

Concocted by PR men eager to turn the director Ernst Lubitsch into a brand name, the phrase, “the Lubitsch Touch” has long been used to describe the unique style and cinematic trademarks of director Ernst Lubitsch. It’s hard to pinpoint exactly what “the touch” is but film historian Richard Christiansen probably put it best with this quote: “The Lubitsch Touch” is a brief description that embraces a long list of virtues: sophistication, style, subtlety, wit, charm, elegance, suavity, polished nonchalance and audacious sexual nuance.”

I only mention “the touch” and its importance because there’s no better representation of it than his film The Shop Around the Corner. Hitting every bullet point Christiansen mentioned, the film spins a tale so utterly delightful, so saccharin sweet, Willy Wonka couldn’t do a better job. The film—about two employees at a gift shop can barely stand each other, without realizing that they are falling in love through the post as each other’s anonymous pen pal—has been remade multiple times (one of which will make an appearance on this list) for the stage and screen for a reason: audiences, no matter the decade, love that “the Lubitsch Touch”.

Sailor Monsoon

33. Definitely, Maybe (2008)

In the midst of a rather amicable divorce, a former political consultant, Will Hayes (Ryan Reynolds), agrees to tell his daughter Maya (Abigail Breslin) the truth about his past, his relationships, and how he met and fell in love with her mother. He changes the names of the three women with whom he had meaningful relationships, including his soon-to-be ex-wife, while Maya attempts to piece together the truth to discover which woman became her mother (whose real name is Sarah). The mystery of who is Maya’s mother hits a snag as an emotional Maya realizes it doesn’t matter who her mother is because she and Will are getting divorced anyway. Every single romance/would-be romance in Definitely, Maybe is a treat to watch, but it’s the father-daughter relationship here that brings the heavier emotion.

Definitely, Maybe is full of 90’s nostalgia, taking us back to the era before cell phones and email as Will works for the 1992 Clinton campaign. He marvels at the rising price of cigarettes, becomes disenfranchised with politics as the Clinton-Lewinsky scandal breaks and finds frustration in internet dial-up. And then there is the fashion and the music, as campaign workers celebrate Clinton’s win in the presidential primaries with Vanessa Williams’s ‘Save the Best for Last’ and April introduces Will to Kurt Cobain and Nirvana. There’s plenty to love about this movie, and you get the added bonus of watching Kevin Kline as boozy, opinionated Hampton Roth, an author, and professor who is dating Summer when she first meets Will. Really, it was difficult to find fault with anything in this movie. Perhaps the ending was tied up a bit too neatly? But it’s definitely perfect for the movie. Maybe. 

Romona Comet

32. Splash (1984)

Splash was so successful that Disney immediately put the Little Mermaid into production, created the name Madison, which became one of the most popular names for newborn girls in the early 21st century and created an entire generation of sexy cryptid fetishists. That last part might be speculation on my part but Del Toro did kinda remake this decades later where the characters actually smash uglies, so this had to have awoken some weird feelings in some youths, I’m just saying. But Splash ain’t just for the weirdos. It’s a heartwarming comedy that feels a tad sitcom-y but its charm and likeability (the world really needed more films that paired Hanks with Candy; their chemistry is off the charts good in this) trump its TV show/movie quality.

Sailor Monsoon

31. About a Boy (2002)

To recommend a Hugh Grant film is to essentially recommend Hugh Grant. He plays the same character in every film he does, which pretty much means that if you don’t like one of them or him in general, odds are you won’t like any of them. If you don’t like him, there’s nothing I can say about About a Boy that will sell you on it. But on the flip side, if you do like him, I really don’t have to say much to convince you to check it out. It’s another energetic comedy starring the impossibly charming Hugh Grant who stutters and stammers his way through every line and makes snide and cynical comments about everything but in the end, learns the power of love/grows up which in turn makes him slightly less of an asshole. There are no surprises or twists to the narrative. You know exactly what this film is before you watch it but the difference between this and all the other predictable romantic comedies? This one has Hugh Grant.

Sailor Monsoon

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What do you think of the selection so far? What are some of your favorite Rom Coms from over the years? Maybe they will show up further on the list!

Author: Romona Comet

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