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.
50. The Best Man Holiday (2013)
Fourteen years after the events of The Best Man, professional running back Lance Sullivan (Morris Chestnut) is a handful of yards away from breaking the all-time rushing record in the NFL. He’s also still happily married to Mia (Monica Calhoun) and they have four children. With Christmas approaching, Mia invites their old friends to the Sullivan home for the holidays.
Dare I say that The Best Man Holiday is even better than The Best Man? The ensemble is still amazing, and just like the first film, you truly feel these characters’ connections to one another. The history between them, dating all the way back to college, is palpable and real, and I really believe that’s a difficult task to pull off with an ensemble of this size. It would be easy to focus solely on one or two characters and shove the others to the background, but The Best Man Holiday gives ample and much deserved time to everyone, and thankfully the movie doesn’t suffer for it.
Expect plenty of melodrama, but there is also a lot of raunchy humor and tender moments. I really wasn’t expecting the amount of devastation I would feel towards the end of the movie, but that’s how skilled director Malcolm D. Lee has been at weaving a cohesive story over two movies with a group of characters that can, at times be unlikeable, but are also easy to care about and for.
–Romona Comet
49. Keeping the Faith (2000)
Brian (Edward Norton) and Jake (Ben Stiller) have been best friends since childhood. Both are also men of faith and fairly young in leading their respective congregations – Brian as a priest, and Jake as a rabbi. Whereas Brian is obviously unable to form romantic relationships, Jake is doing everything in his power to avoid them, frequently overwhelmed and put off by the mothers of his synagogue trying to set him up with their single daughters. Brian and Jake get a blast from the past when their third childhood best friend Anna (Jenna Elfman) calls to reconnect.
Keeping the Faith is driven by spirituality, morals, and how religion may or may not define the characters. It’s set up as a romantic love triangle, with Jake and Anna dealing with their feelings for each other despite the fact that (gasp) Anna is not Jewish. Meanwhile, oblivious to Jake and Anna’s secret relationship, he also finds himself attracted to her and questioning the vows he took to devote his life to God and ministering. The movie strikes a nice balance between sweet and zany and despite feeling maybe twenty minutes too long, it’s a really endearing romantic comedy about the endurance of faith and friendships.
–Romona Comet
48. Long Shot (2019)
Obviously, I’m not too hard to please when it comes to romantic comedies, but even I can admit that they’re quite formulaic and it takes a really special script and pairing to bring about anything new or remotely original. Long Shot doesn’t exactly subvert the genre, but it also doesn’t need to. With a biting, witty screenplay from Liz Hannah and Dan Sterling, director Jonathan Levine sets an unlikely (but not impossible) romance against the backdrop of the country’s current political and moral shortcomings.
What makes this film truly work is the remarkably adorable chemistry between Rogan and Theron. The tagline is beyond accurate: Unlikely, but not impossible. Rogan’s Fred Flarsky is loud and occasionally crass with a terrible fashion sense, but he is also honest and morally sound. Rogan plays Fred as a lovable, heartfelt mess with ease and never once did I ask myself what Charlotte could possibly see in him. Charlotte, on the other hand, is beautiful and intelligent, but also down to earth and kind which doesn’t seem to be much of a stretch for Theron. While you would never expect a woman who looks like Charlotte to fall for a guy who looks like Fred, their attraction to one another is so immediate and feels so authentic that you never doubt it. You root for them from that very first glance across a crowded dance floor.
–Romona Comet
47. Much Ado About Nothing (1992)
When one thinks of the works of Shakespeare, epic historical war melodramas and tragic teen romances come to mind, not a lighthearted tale filled with whimsy and merriment. What sets Much Ado About Nothing apart from the Bard’s more popular plays (technically they’re all popular but this ones less so) is that schemes and bad timing don’t win the day. This one checks all the typical Shakespeare boxes (a couple of star crossed lovers beseeched by treachery) but unlike his other downbeat plays, love ultimately wins the day.
Try as he might, the evil Keanu Reeves can’t destroy the connection formed between Claudio (Robert Sean Leonard) and Hero (Kate Beckinsale) and try as they might, Beatrice (Emma Thompson) and Benedick (Kenneth Branagh) can’t stay away from each other even though both are terrified of getting hurt. Juggling two different love stories each filled with his signature wit and fantastic characters, Much Ado About Nothing is Shakespeare at his most playful, his most cheerful and his most romantic.
–Sailor Monsoon
46. Better Off Dead…(1985)
I had honestly forgotten what a bizarre movie this was. From the very opening scene where we get a shot of Lane’s (John Cusack) bedroom, literally covered in nothing but photos of his girlfriend Beth, to the horrible meals that Lane’s mother makes the family that continually get worse until the concoctions come to life to slide off of the dinner plates to freedom. Like Lane’s mother’s cooking, the recurring gags continue to get more and more absurd, but it felt like director Steve Holland was taking us into the mind and imagination of a teenage boy, so I was willing to buy into the silliness.
Eventually, Lane does meet Monique (Diane Franklin), the French student across the street. Unfortunately, with Monique comes the creepy pair of Mrs. Smith and her son Ricky (Dan Schneider), who are hosting Monique in their house. They become increasingly controlling and possessive of Monique and instead of being funny, it’s like watching an abusive relationship blossom in the midst of other humorous moments. Better Off Dead is a mish-mash of oddities. Part coming of age teen comedy, part rom-com and part parody, I couldn’t really figure out what this movie wanted to be, and I’m not sure it knew either. But that’s okay. There’s enough offbeat humor to keep it afloat.
–Romona Comet
45. Something’s Gotta Give (2002)
I am a big fan of Nancy Meyers. The Holiday and Father of the Bride are two of my favorite movies. Not only are her films well written and romantic (most of them!) but they’re all gorgeous to look at. I will never own a beach house like the one Diane Keaton owns in Something’s Gotta Give, but boy I wish I could. That being said, I was really thrilled that Meyers wrote and directed a romantic comedy with two older actors in the leads, and how could anyone go wrong with Jack and Diane? The two share an undeniable chemistry that we first got a glimpse of when they co-starred together in Reds (1981). Diane shines as Erica, a divorcée who seems content with being single but is then so open and accepting to the love she feels for Harry that it’s absolutely heartbreaking. Jack is… well, Jack! Intelligent, biting and a bit arrogant, but still able to handle the emotional scenes with such vulnerability that you almost forget that it’s Jack Nicholson.
Something’s Gotta Give is funny and charming and maybe it doesn’t stray too far from the rom-com formula, but the performances from Jack Nicholson and Diane Keaton make it one of the better romantic comedies (and movies in general) of the 2000s.
–Romona Comet
44. Always Be My Maybe (2019)
It seems like, at least from my experience anyways, that men and women are more willing to accept cliches as long as they’re in films that they enjoy. It’s a bit of a generalization but it seems like men have no problem turning a blind eye to the ridiculous tropes of action movies, while women adore “chick flicks” that are little more than a checklist of genre staples. I’m trying to avoid regurgitating old hackneyed stand up bits (men do this, while women do this!) or the ridiculous “Men are from Mars, Women are from Venus” bullshit but it certainly seems true because whenever I’m forced to watch a romantic comedy, I immediately recognize the clichés and they infuriate me.
The completely-out-of-nowhere third act conflict, which leads to a race against time with the main character having to head to an airport to catch the woman he loves before she leaves forever and yada yada yada you know the rest. Romantic comedies clichés are the worst, which makes Always Be My Maybe that much more refreshing. The two leads have a natural chemistry and play off each other nicely, the dialogue is witty and feels naturalistic, the celebrity cameo is hilarious and while it doesn’t manage to avoid every cliché, the ones that make it in, are a lot more tolerable due to the sharp writing and likable leads. If you’re a fan of romantic comedies, this one is a must watch.
–Sailor Monsoon
43. Moonrise Kingdom (2012)
Wes Anderson’s films have a signature style that’s so distinct, so precise, it almost becomes too much. He is among a handful of directors who’s films are so unmistakably their own, their names have become synonymous with a particular style. If I say something is Burton-esque or Cronenberg-ian, you know exactly what I’m talking about. But that stamp of ownership comes at a price: the price of alienating a large chunk of your audience and the risk of becoming an unintentional self parody. His style almost becomes a detriment to the films themselves. It’s hard to look past the symmetrical camera movements and hipster aesthetic, when it’s present in every one of his films. Even if you love his films, there will be at least one that feels like a bad imitation of his work and for me, that was Moonrise Kingdom.
The first time I saw it, all I saw was the superficial aspects that make up his work. The quirky characters, the sudden whip-pans, the distractingly omnipresent colors, the specific line delivery, things that never bothered me in his other films, suddenly became annoying. I couldn’t stand it. But then I watched it again and this time, I focused on all the things that really make up a Wes Anderson film (the delightful over confidence of youth, the painful regret that comes with age and how amazing new love feels like) and I liked it a lot more. Anderson is not an easy director to love but if you can look past his stylistic shtick, you’ll find an entire filmography of original films, with Moonrise Kingdom being one of his best and most heartfelt.
–Sailor Monsoon
42. To All All the Boys I’ve Loved Before (2018)
To All The Boys I’ve Loved Before is the kind of movie I’ve been dying to see more of. Inclusive, heartwarming and genuinely funny. Yes, it touches on a few rom-com tropes, but I don’t consider that to be a negative if they’re done correctly (which here, they are. Mostly). Lana Condor’s Lara Jean is smart and funny with just enough snark to make her pretty damn endearing. She is a strong female lead who doesn’t back down when the resident mean girls are trying to intimidate her (as the high school mean girls so often do in these kinds of movies), or when she was struggling with her own feelings for the boys in her life. She’s also relatable as hell. She loves Golden Girls marathons, she’s afraid of driving, has very few friends and brings books with her on school ski trips (who doesn’t?). Noah Centineo (so reminiscent of Mark Ruffalo that it was a little eerie sometimes) was charismatic as Peter, Lara Jean’s love interest. His character was so wonderfully fleshed out and proved that it was possible to be interesting and compassionate and *still* be Mr. Popular.
I really loved this film. The acting, the script, the cinematography, the music… it all clicked in a way so many rom-coms fail to do these days, and it is by far one of the best teenage romantic comedies out there.
–Romona Comet
41. The Holiday (2006)
Like most romantic comedies, the plot of The Holiday is fantastical and requires an extension of belief, but if you’re willing to do that (and why wouldn’t you be?), you’ll find The Holiday is charming and romantic. Out of the 5 main characters, each has experienced love differently. Arthur married the love of his life and remained married for 40+ years until his wife’s passing. Graham is a widower with two little girls, Miles is in a relationship with an aspiring actress who is clearly out of his league (and he knows it), Iris has been suffering from unrequited love from a colleague who continues to take advantage of her affection and Amanda is a woman who has difficulty opening herself up to love because of her parents divorce. I have to imagine at least one of these scenarios could be considered relatable to anyone watching, and I felt for all of them on a different level.
I still feel like the score Miles wrote for Iris was one of the best parts of the movie (“I only used the good notes”), along with his singing of various film scores in the video store, which I found stupidly charming. I’m also a sucker anytime a man in a rom-com cries when he sees the love of his life (I’m looking at you Jude Law). One of my favorite romantic movies to watch during the holiday season and a rom-com that doesn’t get the attention it deserves.
–Romona Comet
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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!
