The 50 Greatest Romantic Comedies of All Time (30-21)

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.

30. My Big Fat Greek Wedding (2002)

I don’t think this generation remembers or even knows how huge this film was. Everybody saw this fucking thing when it came out. It played in theaters eleven weeks longer than Titanic and that was in theaters for a year straight. It was a cultural phenomenon that took the world by storm. This is made all the more surprising due to the fact that it’s a romantic comedy with a predominantly non-white cast.

Nia Vardalos brought America together with her delightful tale involving a young Greek woman (Vardalos) who falls in love with a non-Greek (John Corbett) and struggles to get her family to accept him while she comes to terms with her heritage and cultural identity. A love letter to her Greek ancestry and a love story that deals with family themes that anyone can relate to, My Big Fat Greek Wedding is a rare treat that everyone can like, Greek or not.

[Sailor Monsoon]

29. Moonstruck (1987)

So few romantic comedies in history have ever been deemed Oscar-worthy. But occasionally one comes along and does everything right. Skillful direction, a strong screenplay and mesmerizing performances capable of circumventing what you generally find in a formulaic rom-com. Moonstruck was a movie that nailed all three, and in return earned six Oscar nominations and went home with three for Cher, Olympia Dukakis, and writer John Patrick Shanley. Nic Cage has a certain… reputation for playing cooky characters, but his performance in Moonstruck as lovesick, temperamental Ronny Cammareri is, in my opinion, one of his very best. His Italian drenched monologue about love and how flawed it is remains one of my favorite scenes in rom-com history.  Cage and Cher are the focal points of the movie, but the entire cast delivers, and there is not one storyline that suffers from weak writing or character development.  

Moonstruck is a witty, warm movie about love, but not in the way so many other romantic comedies are about love. It’s not about fairytale love, but messy, complicated love that can be both joyful and painful, and that is what sets it apart from so many others in the genre.

[Romona Comet]

28. Notting Hill (1999)

Twenty years ago Julia Roberts had two romantic comedies released within two months of each other. The first was Notting Hill where she played Anna Scott, a famous actress who found love with an awkward but charming Brit played to perfection by Hugh Grant. The other was Runaway Bride featuring the much-anticipated reunion between Roberts and her Pretty Woman co-star, Richard Gere. While both films were box office successes, it was Notting Hill that won critical acclaim and to this day remains Roberts’s best-reviewed romantic comedy.

I suppose it’s fair in some ways to compare Notting Hill to Four Weddings and a Funeral, also written by Curtis, but frankly, I find Notting Hill to be the far superior film. It’s more polished, it’s funnier and more importantly, Roberts and Grant’s sizzling chemistry is palpable and helps drive the believability of an otherwise unrealistic premise. They keep us emotionally invested in their journey, so much so that I was willing to overlook, and admittedly maybe even celebrate, the somewhat contrived ending.

Witty, poignant and delightfully funny and romantic, I truly believe the time has come to call Notting Hill a classic.

[Romona Comet]

27. Serendipity (2001)

With a plot that requires a lot of faith, acceptance of some contrivance plots, and discounting some “glaring” plot holes (how does Sara get on an airplane without her ID when she and Eve switch wallets? Did that light cashmere glove really fly that far in the skating rink in the snow?), Serendipity ultimately comes down to whether or not John Cusack and Kate Beckinsale, have enough chemistry to root for them to ditch their likable significant others and surrender to fate. The answer is yes, yes they do. It’s palpable enough that it’s okay that they are barely on screen together after their initial meeting, because you want to stick around and follow them on their journey back to one another.

With fun, comedic turns from Molly Shannon, Eugene Levy and John Corbett (“the problem is you can’t fight off an army of blood-thirsty Vikings with a shenai, it’s illogical.“), Serendipity is warm, fluffy and charming. There’s no room for logic and explanation in this movie. As Sara says… “You don’t have to understand. You just have to have faith.”

[Romona Comet]

26. 13 Going on 30 (2004)

13 Going on 30 is definitely a romance, but it’s also about Jenna’s redemption as a person. She realizes she’s gotten everything she wanted in life, but she’s increasingly appalled at what her future self did to get there. Jennifer Garner is wonderful in the role of a thirteen-year-old in a thirty-year-old body. Jenna’s naiveté and childlike wonder could have so easily been cringy and annoying in the hands of a less capable actor, but Garner manages to come across as sweet and charming while holding a sense of confidence and determination that is hard to find in a lot of insecure thirteen-year-olds.

The movie touches upon what we can and can’t achieve when we lack a moral compass. Obviously, it’s better to be a good person than a back-stabbing bitch, even if the latter makes the path to success much easier. Jenna was able to see who she would turn out to be, and with a second chance, became who she really wanted to be instead. 13 Going on 30 doesn’t break any new ground in terms of the genre, but it’s a sweet, funny movie with a captivating performance by Garner and a swoon-worthy leading man in Ruffalo.

And I won’t lie, I believe the scene between Jenna and Matt on the swings in the park is one of the most romantic scenes in rom-com history.

[Romona Comet]

25. Ruby Sparks (2012)

A successful young novelist named Calvin (Paul Dano) is dealing with a terrible case of writer’s block and an even worse case of the can’t-find-a-date blues. Things turn around however, when he starts writing about “the perfect girl”. Zoe, his idealized creation, serves as his muse and helps him start writing again but due to some unexplained fantastical magic, his creation suddenly comes to life and is now a living, breathing person.

Ruby Sparks, much like 500 Days of Summer, is a film about idealism and expectation within relationships. The male leads of both films are assholes who can’t relate to their partners but the difference is, Calvin (the lead of this) realizes that there is no such thing as “the perfect woman” and that changing a woman to fit your impossible standards, is garbage. This is a film with a very important message at its core thats surrounded by genuine emotion and the undeniable charm of Kazan.

[Sailor Monsoon]

24. The Wedding Singer (1998)

The Wedding Singer was the first of three movies Sandler and Barrymore starred in together – the other two being 50 First Dates (2004) and Blended (2014) – and in my opinion, it remains their best. This film is where we were first introduced to their sparkling, romantic chemistry and their chemistry is really the only thing that has remained consistent throughout the other two films. Sandler is known for his sophomoric, gross-out humor, and yes he’s comedically gifted, but there are moments in The Wedding Singer where he’s able to shine as an actor as well. He’s not playing an immature man-child or a selfish jerk, but a real man who is dealing with heartbreak the only way he knows how through dry humor. Barrymore is as sweet and adorable as ever, and the two play off of one another with natural, attraction-tinged banter.

The entire movie is an aggressive but charming homage to the 80’s and everything from Miami Vice and Billy Idol to CD players is represented. I still firmly believe that The Wedding Singer is Happy Madison’s best production and Sandler’s best film to date (with Punch Drunk Love a very close second). If I see it on television, I tend to turn it on to watch no matter where it might be in the movie. It’s sweet and funny without needing the juvenile humor that so many of Sandler’s films are known for. The characters are well written and even though it has a simple, predictable premise, the 80’s nostalgia and the chemistry between Robbie and Julia makes it so worthwhile.

[Romona Comet]

23. Silver Linings Playbook (2012)

After almost two decades of making weird ass independent films, David O. Russell finally hit his stride in the 2010’s. The five films he released that decade amassed a staggering 25 Oscar noms, which, by itself is an impressive feat but the fact that one of those films only earned one nom and the other was a notorious bomb, is all the more awe-inspiring. While American Hustle  received the bulk of those noms (some would say undeservedly), Silver Linings Playbook nabbed a respectable six, with Lawrence being the only one to go home with the gold. I’m not saying the Academy fucked up, nor am I saying it should’ve gotten as many noms as American Hustle. All I’m saying is Silver Linings Playbook is Russell’s best film and is far better than Lincoln or Les Misérables or whatever bullshit won that year. The performances are all superb, the writing is exceptional and it doesn’t reek of Oscar bait. It’s a charming love story that gets heavy when it needs to but never gets sappy. Wait, Argo won and The Master wasn’t even nominated? Goddamn it Academy. You had one job.

[Sailor Monsoon]

22. Say Anything… (1989)

An underachiever (John Cusack) and a valedictorian (Ione Skye) fall in love a couple of weeks before she goes off to college. In addition to being good enough to compare to the best of Hughes’ work, it’s a film that made me re-evaluate Crowe’s career. I had originally written him off as a one hit wonder that somehow got lucky but now having seen this, it’s clear to me that it wasn’t luck. He used to have talent. A shit ton of it in fact because this film is really something special. The performances were all spectacular, the characters all felt real (which is rare in a teen comedy), the drama was believable and Lloyd Dobler might be the most likable character in cinema history. I instantly fell in love with him and since he loved Diane, I loved Diane. Their relationship, their romance is the only one I’ve ever seen in a rom-com where I actively rooted for them to be together and hoped they stayed together after the credits roll.

[Sailor Monsoon]

21. Pretty Woman (1990)

Pretty Woman is formulaic and overrun with rom-com tropes… though it’s possible a few of those tropes originated in this film. But it’s also propelled by Julia Roberts’s performance. She’s the Cool Girl, adorably quirky and smart, despite some of her naivety in terms of social status and class. Vivian comes across as calm and confident, but her uncertainties are evident in her constant fidgeting. Roberts is energetic and charming in the role, whereas Richard Gere is appealing but subdued as Edward. He simply seems tired of his path in life, despite having essentially everything he could possibly want. Gere and Roberts play well off of each other. Their chemistry is palpable and fuels the movie, making it easier to believe in the Cinderella fantasy.

There is nothing realistic about Pretty Woman. It’s a fairytale through and through, and if you can overlook some of its glaring issues, it’s something of an endearing romance. If nothing else, it’s had an incredible impact on pop culture, from Roberts’s shopping spree and subsequent takedown of some snotty saleswomen (“You work on commission, right? Big mistake. Big. Huge!”), to her iconic red evening dress. Honestly, sometimes it’s nice to just turn off your brain and get lost in a mindless fantasy, and that’s what Pretty Woman is.

[Romona Comet]

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