Well, we’ve finally reached the summit: the 10 most definitive romantic comedies of all time. Unlike the other sections of this list, there is not a movie here that approaches “bad.” As always, some are better than others, despite the order. But one thing is for sure: if you plan to have a rom-com binge-a-thon soon, this is where you start, no questions asked. In fact, after reading this, you should go do that and report back.
10. Some Like It Hot (1959)
What’s funnier than men dressing in drag? Depends on who you ask. It’s Billy Wilder again with a fictional story of two musicians – Joe (Tony Curtis) and Jerry (Jack Lemmon) – who witness the St. Valentine’s Day massacre in Chicago and leave town. But, since the mob has ties everywhere, they need to disguise themselves as best they can: as women in an all-girl band on their way to Florida. Now Josephine (Curtis) and Daphne (Lemmon), the two find themselves enjoying their time with the women, especially with Sugar Kane Kowalczyk (Marilyn Monroe), who Joe tries to win over while disguising himself as another man. Meanwhile, Daphne/Jerry finds himself being pursued by a millionaire (Joe E. Brown) who won’t take no for an answer. As you can see, this leads to plenty of ridiculous situations that play themselves out well, thanks to Lemmon and Curtis and their go-for-broke performances. Surprisingly, while the Sugar Kane-Joe pairing gathers more steam (literally and figuratively), the Osgood (Brown)-Daphne pairing is the more interesting couple, especially at the film’s conclusion. It’s not as romantic as the other films on this list, but its certainly as funny. Besides, nobody’s perfect.
9. Pretty Woman (1990)
It’s become a go-to trope in the romantic comedy genre (or, at least, variations on it), but Pretty Woman pretty much created the “hooker with a heart of gold” motif. It won Julia Roberts a Golden Globe and grabbed her an Oscar nomination, blowing up her popularity to an unseemly level. Roberts had been around for a few years, but putting her opposite Richard Gere and in streetwalker wardrobe worked. Directed by Garry Marshall (when he still made decent films), Pretty Woman became a cultural landmark in the early 90s, thanks to the lead performances and a number of stand-alone moments that stuck in moviegoers’ collective psyche: the red dress, the polo match, the game of necklace keep-away. Roberts would slowly find her roles as a serious actress, but in 1990, it was tough to find a better leading lady for a rom-com.
8. Bringing Up Baby (1938)
You know what really helps people fall in love? Jungle cats. In 1938, after being fired by RKO when his adaptation of Gunga Din was going poorly, Howard Hawks jumped on board Bringing Up Baby, a screwball comedy starring Cary Grant and Katharine Hepburn. The film was written specifically with Hepburn in mind, meant to fit her personality as Susan, a free-spirited woman who meets a paleontologist named David (Grant) the day before he is meant to marry a fellow scientist. Unbeknownst to David, Susan is the niece of a probable donor to his museum. She also owns a leopard named Baby and tries everything she can to get him to accompany her to Connecticut to see Baby, while trying to keep him from going through with his marriage. Antics ensue, of course, while Hepburn gets her feel for the type of comedy needed for the film. The film was a flop upon its initial release, but slowly became an incredibly popular landmark of the studio system era. It also contains what is suspected to be the very first use of the word “gay” as a term for homosexuality in major media, from a line improvised by Grant on the spot. Regardless: Cary Grant as a nerdy scientist (at least, trying to be one) is a fun departure from his typical big screen persona.
7. The Graduate (1967)
A year after his directorial debut with Who’s Afraid of Virginia Woolf?, Mike Nichols softened his camera a bit with a look at love, success, and loneliness in 1967’s The Graduate, based on the novel by Charles Webb. Starring Dustin Hoffman as recent college graduate Benjamin Braddock, it grabbed seven Oscar nominations, winning one (Director). Now that Benjamin is done with school, he finds himself struggling with his “next step,” only to be drawn into an illicit affair with the wife of his father’s business partner, Mrs. Robinson (Anne Bancroft). Shortly thereafter, Benjamin finds himself falling for Mrs. Robinson’s daughter Elaine (Katharine Ross), all while trying to hide everything at once. The Graduate found a way to capitalize on Hoffman’s ability to play awkward, easily succumbing to the appeal of Bancroft’s Robinson. Benjamin is rumbled out of his funk by her friendly hand (and more), but has to find a way to escape the rabbit hole he’s pulled into with this affair. While the famous ending can be viewed as a “happy” one, it says more about the nature of youth and acting on impulse. That grand gesture may feel right at the time, but when all is said and done and you get what you want, what then? Where do you go from there?
6. The Apartment (1960)
Apparently, there was a time in history when your best chance for professional advancement was to let people have sex at your house. True story. Billy Wilder’s The Apartment stars Jack Lemmon as C.C. Baxter, an insurance salesman who tries to rise within his organization by allowing executives to borrow his place for extramarital affairs. Unfortunately, when his married boss Sheldrake (Fred MacMurray) gets added to his rotating list of “borrowers,” Baxter falls for the woman he is cheating on his wife with, an elevator girl named Fran (Shirley McLaine). Of course, Fran has no idea that she is the latest in a string of affairs Sheldrake has engaged in, no idea that Baxter is fond of her, and believes Sheldrake will leave his wife. The three lead performances are outstanding, only furthered by the always excellent hand of Billy Wilder. Wilder relationships are better than real ones, which means the conflict is always more interesting and, most of the time, funnier. The Apartment melds the romantic comedy with the office comedy in a way that adds flavor to both sub-genres and helps it stand out as one of the best written and funniest of Wilder’s impressive filmography.
If you had to start somewhere, why not start with one of film’s greatest icons? Charlie Chaplin’s Tramp character had been in numerous shorts, but found his big-screen bearings in what is one of the most romantic films of all time. City Lights features the Tramp falling in love with a destitute blind girl (Virginia Cherrill), when she mistakes him for a wealthy duke. When he learns that she can have an operation which may restore her sight, the Tramp goes on a series of adventures to earn money, using a relationship he has with a wealthy man to slowly build up income. The Tramp does all this, all while knowing that, when she can see, she will see he is not the rich man he has pretended to be. Chaplin’s physical humor always brings his silent films to life and City Lights is no different. However, unlike his other comedies, this one is injected with more emotion. His films always contains strings of satire, but not the undercurrent of romantic love like City Lights does. Still packed with plenty of laughs, City Lights stands out as the true gem of Chaplin’s career for saying more about love in silence than the vast majority of other films can say with oodles of dialogue.
4. When Harry Met Sally… (1989)
If this was a list of just modern romantic comedies, this film would probably be #1. But, alas, there were some that did it long before Rob Reiner did. All that in mind, When Harry Met Sally… is still the gold standard for romantic comedies made in the last 30 years. Starring Billy Crystal and Meg Ryan, the film documents their relationship as two people going through their own romances, always bumping into each other and eventually turning to each other for support and guidance. But the question always remains: can a man and woman have a friendship that strong without always wanting sex? The film as a whole revolves around that question, providing a template for every “will they, won’t they” scenario possible as they move through their lives separately. The movie spans over a decade; Reiner intercuts the narrative with interviews with real-life couples, explaining their relationships and how, despite all our differences, we all generally go through similar things. Crystal and Ryan give two of their best performances and, despite both having taken a bit of a dive in terms of movie roles as of late, they will always have this shiny little glimmer of hope that, if you write a good script, get a good director, and get two leads together with strong chemistry, it’s possible to tell a charming, relatable story about love on screen.
3. Annie Hall (1977)
Whether or not the female characters Woody Allen writes are accurate or not is beside the point. The majority of them are extremely memorable. For his entire career, he has basically written/directed one movie annually, but grabbed his only Best Picture Oscar with his seventh feature film, Annie Hall (beating Star Wars). The film is the story of a relationship between Alvy (Allen) and the title character (Diane Keaton) and how it evolves over time. Alvy is a pessimistic neurotic, while Annie is fun and fancy free, while a bit ditzy. They follow a normal trajectory: meet cute, fall in love, things are great, things get sour, things fall apart. What Annie Hall does differently is subvert that process. We see behind the curtain and see what happens when two very different people find something special, only to watch the ship sail from both sides. Both Keaton and Allen are marvelous as the leads, as they navigate a relationship that, for lack of a better term, needs to happen. Unlike most rom-coms that have you believe happy endings only exist when couples end up together, Annie Hall acknowledges that, sometimes, it may not work out. But, the time together is necessary for growth and maturity. But, until that hole is filled by someone or something, misery can be expected. Allen never shies away from that and, with such well defined characters, it becomes all the more real.
2. It Happened One Night (1934)
Frank Capra’s It Happened One Night was the first movie to win all five major Oscar categories (Picture, Director, Actor, Actress, Screenplay), a feat that wouldn’t be matched until 1975 (One Flew Over the Cuckoo’s Nest), and for good reason. Ellie (Claudette Colbert) is the heiress to a wealthy father who, upon learning she had a secret wedding to a fortune-hunter, wants to annul the marriage. Ellie runs away and boards a train in the hopes to meet up with her secret husband. There, she meets a newspaper reporter named Peter (Clark Gable), who says he will help her if he gets the rights to her story. Otherwise, he turns her in and collects the prize money. They begin to rely heavily on each other as they travel together – Peter explains how a man should get dressed; Ellie outdoes Peter by flagging down cars to hitchhike in her own way. But, through it all, they slowly fall in love with each other, despite the many reasons they keep telling themselves they shouldn’t. Colbert and Gable were not the first choices – Gable is rumored to have been “lent” to the studio to make the film; Colbert’s last film was directed by Capra and, after its failure, swore to never work with him again. But the stars aligned, as they say. What results is one of the greatest romantic comedies of all time, one of the greatest road trip movies of all time, and a template for how a rom-com should be made. It’s not about triangles, affairs, or stupid jokes; it’s about love and love alone.
1. The Philadelphia Story (1940)
And so it comes to this. What’s the recipe for the perfect romantic comedy? Hire a good director (George Cukor). Find good source material (play by Philip Barry). Cast the most handsome man you can find (Cary Grant). Cast the most identifiable Everyman you can find (Jimmy Stewart). And, for fun, why not cast the greatest actress alive (Katharine Hepburn)? Mix it up and you have The Philadelphia Story, the definitive romantic comedy. Just before wealthy Tracy Lord (Hepburn) is to be married, her ex-husband C.K. Dexter Haven (Grant) shows up with a tabloid reporter named Macaulay Connor (Stewart), throwing wrenches into the ceremony. From there, we have something of a love quadrilateral, as Dexter is bent on causing trouble, not expecting Macaulay to fall for Tracy, too. In all the hustle and bustle of wedding planning, drinking too much, covering up intentions, and all-purpose mischievousness, all the characters begin to see exactly who they are. Tracy sees her domineering nature, Dexter sees his playboy persona, and Macaulay…well, he sees something he never expected to see right in front of him. The Philadelphia Story is a whirlwind of romance and comedy, with a semi-unexpected ending where everybody seems to be happy. But, among all the happy endings romantic comedies give us, there’s something about how this little parable ends that can’t help but be enjoyed.
So, there you have it: 50 definitive romantic comedies. There are obviously going to be some disagreements about them and, while the order of the top 10 may not be what everyone envisions, it can’t be denied that they belong here. Thanks for reading–and now, the floor’s open for discussion and debate.
– Joshua Gaul