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Greatest Romantic Comedies


Happy Valentine’s Day: Here are the 50 Best Romantic Comedies

The Greatest Romantic Comedies Part 2

So, we’ve arrived at the top 25, slowly creeping toward those films that are exactly what a romantic comedy should be. We’ve seen films that fall into the category, but lean more toward other genres. We’ve seen romantic films that are funny enough to be comedies, but don’t entirely represent the spirit of the rom-com, despite being brilliant films. Now, we form a clearer picture of what a romantic comedy is. Not all of the films in this section are necessarily “good,” but they’re all iconic, definitive romantic comedies (hence their inclusion). Memorability does not necessarily come partnered with quality. It means right place, right time.

About a Boy (2002)
Image: Universal Pictures

#25. About a Boy (2002)

A surprisingly nice double feature with The-40-Year-Old-VirginAbout a Boy stars the ever-charming Hugh Grant as Will, an immature man nearing middle-age who finally grows up, thanks to a little boy named Marcus (Nicholas Hoult). Based on a best-selling novel by Nick Hornby, About a Boy follows Will as he tries to serve as a “plaything” for single mothers, only to meet Marcus and have his world turned upside-down. He eventually finds himself serving as a surrogate father to this pre-teen, who spends his time trying to cheer up his emotionally disturbed and chronically depressed mother (Toni Collette). Enter Rachel (Rachel Weisz), a single mother who Will can’t help but fall for, despite the dishonest manner in which they met. Grant gives one of his better, more layered performances here, as he shifts between a man who feels image is of utmost importance to one who begins to care deeply about others, even if those others feel like a burden. Hornby’s novels tend to make good films if in the right hands – About a Boy is no exception, with an Oscar-nominated screenplay.

(500) Days of Summer
Image: Fox Searchlight Pictures

#24. (500) Days of Summer (2009)

It literally begins with “This is a story of boy meets girl, but you should know upfront, this is not a love story.” So begins the nonlinear narrative story of Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel). Summer begins working at the greeting card writing company at which Tom is employed, though he dreams of being an architect. The story focuses on Tom’s unwavering belief that Summer is the “one,” despite her constant statements that she doesn’t want anything serious and may not even believe true love exists. What results is an imaginative jump between happy days and sad days, re-imagining memories Tom believed were positive, but were simply clouded by his vision of love. Few romantic comedies can boast an ending that isn’t quite a happy one, but can still make the audience smile. (500) Days of Summer manages to do that, with the help of a fine “indie” soundtrack. Also: look for an early performance from Chloe Grace-Moretz as Tom’s younger sister, who steals every scene she’s in.

Roman Holiday (1953)
Image: Paramount Pictures

#23. Roman Holiday (1953)

Audrey Hepburn has seen her fair share of criticism, but behind that gorgeous facade, there was a pretty solid actress, if given the right part. She earned her only Oscar win in 1953 for Roman Holiday, the story of a princess getting away from her royal lifestyle. While away from her caretakers, she meets and falls in love with an American journalist, played by Gregory Peck. The story sounds old hat at this point, being redone in the forms of movies like Chasing Liberty and, in a twisted way, Eddie Murphy’s Coming to America. But the chemistry between Hepburn and Peck (not to mention the beautiful shooting locations) is enough to win over even the coldest of hearts. Delineating from the norm and avoiding a perfectly happy ending, Roman Holiday is exactly what it sounds like: a nice vacation away from typical rom-coms, breathing just enough charm and whimsy to make for a joyous experience.

Greatest Romantic Comedies
Image: Universal Pictures

#22. Bridget Jones’s Diary (2001)

Helen Fielding’s 1996 novel was a book for the modern insecure woman: a story told from the point of view of a thirty-something British woman who obsesses about her love life, drinks a bit too much, and documents all of it in a diary (how the book is delivered). Inspired in part by Jane Austen’s Pride and Prejudice, Fielding’s work was adapted for the screen in 2001 by Fielding, with help from Andrew Davies and, you guessed it, Richard Curtis. The movie starred Renée Zellweger as Bridget; at the time, this seemed like an odd choice, given she wasn’t British, in a film based on an award-winning British novel. But it turned out to be perfect casting, as Zellweger gave what may be her best (or, at least, most memorable) performance, earning an Oscar nomination while showing excellent comic timing and going toe to toe with England’s most recognizable talents at the time, Colin Firth and Hugh Grant. The film follows Bridget through a series of misadventures with the men in her life, her job, and her family, all while documenting  her experiences in an attempt at self-preservation. If anything, Bridget Jones’ Diary managed to bridge a gap between British and American romantic comedies, proving they aren’t that different. We all have the same problems, right?

Greatest Romantic Comedies
Image: 20th Century Fox

#21. Say Anything… (1989)

Lloyd Dobler (John Cusack) screwed up hundreds of high school boys with that stupid boombox, didn’t he? Cameron Crowe’s directorial debut told the story of Lloyd as he sets his sights on Diane Court (Ione Skye), the class valedictorian, in the summer after graduation. Lloyd is average at best, setting his goals on very different things than Diane, first and foremost his dream to be a professional kickboxer. But, even as Diane skirts his attempts at her heart, his persistence and unending pursuit eventually wins her over, eventually being her support when her father (John Mahoney) falls into trouble with the IRS. What Say Anything… does better than any other rom-com is making that “never give up” mantra seem like a realistic pattern of behavior. Sometimes the normal guy wins out, yes. But not like this. Cameron Crowe’s screenplay is what makes Lloyd such a lovable character and makes Diane such an unattainable end game. But that boombox. Rarely is a song used as a plot device so clearly (in a non-musical, mind you) than here, as Peter Gabriel’s “In Your Eyes” became the love song to end all love songs. Briefly.


So, we’re through 30. Only 20 more to go, where we all begin to fall into the trap of “this could happen!” It’s nice to have a positive outlook.

 Sleepless in Seattle (1993) - Greatest Romantic Comedies
Image: TriStar Pictures

20. Sleepless in Seattle (1993)

Tom Hanks had been the leading man in romantic comedies before (e.g. Splash). But the same year he took home his first Oscar (Philadelphia), he also starred opposite Meg Ryan in this Best Original Screenplay Oscar nominee about a widower and his son, who takes it upon himself to call a radio show, trying to find his father a partner. When Jonah (Ross Malinger) calls the station, it prompts Sam (Hanks) to pour his heart out about his lost wife and his subsequent loneliness. Among the women who fall head over heels for this man sight unseen is Annie (Ryan), an engaged Baltimore writer who can’t shake her obsession with the possibility of a fairy tale ending. It’s incredibly unrealistic and insanely wrought, but somehow the film found a huge audience in the early 90′s who were dying for this kind of story. Hanks was on his way to becoming the greatest actor of his generation. Meg Ryan was in the midst of her short run of quality performances. And so it became a love story that birthed dozens of imitators in the 90′s and found its place as a universally adored little story. If you haven’t seen it for a while, you might be surprised. Sleepless in Seattle is better remembered as the fairy tale it tries to be, rather than an easy target to lob critical hatred. But, maybe that’s what a rom-com should do.

 Jerry Maguire (1996)
Image: Sony Pictures Releasing

19. Jerry Maguire (1996)

Cameron Crowe had already proved his ability to write and direct a solid romantic comedy (Say Anything…). Renée Zellweger was a near-unknown young actress trying to break into the industry. Tom Cruise was Tom Cruise. These people converged in 1996 to deliver an Oscar-friendly love story surrounding the world of a sports agent and his sudden morality complex. When Jerry (Cruise) is fired for taking an ethical stand, he goes out on his own with only one athlete to represent: the outspoken Rod Tidwell (Oscar-winner Cuba Gooding, Jr.). In addition, a 26-year-old single mom named Dorothy (Zellweger) quits her job at the company to follow him. What results is an expected story of struggle and awakening, both professionally and personally, as Jerry is sent away by his fiancee, eventually spending more time with Dorothy and her son (Jonathan Lipnicki). The love story goes back and forth and, a handful of famous quotes later, they end up together. Filled with decent performances and a witty screenplay, Jerry Maguire provided a jumping-off point for Zellweger, the only Oscar for Gooding’s disappointing career, and one of Cruise’s finer performances. Plus, more memorable quotes than probably any film of the 90′s.

The African Queen (1951)
Image: United Artists

18. The African Queen (1951)

Katharine Hepburn has gone down in history as one of the greatest actresses we’ve ever seen. However, among all those dramatic performances, she has quite a bit of romantic-comedy blood in her (as you’ll see later on this list). One of her Oscar-nominated turns in a rom-com came in 1951′s The African Queen, a silly little story of a riverboat owner who is convinced to take an uptight missionary to attack an enemy boat. Hepburn plays the missionary, named Rose, while the riverboat owner Charlie is played by the great Humphrey Bogart, in his only Oscar-winning role. After the death of her brother at the hands of the enemy, Rose is convinced that she must do her part for the war effort, forcing Charlie to oblige. What results is a mismatched trip up the Ulana River, where the upper-class Rose clashes constantly with the grumpy, lower-class Charlie. Bogart departs from his typical film noir style to play Charlie fast and loose, pairing up perfectly with Hepburn’s anal-retentive Rose. Opposites attract on screen, especially when you’re stuck in close quarters for extended periods of time. The African Queen is no exception.

Love Actually (2003)
Image: Universal Pictures

17. Love Actually (2003)

Christmas + a dozen storylines + every talented British screen actor + Richard Curtis = Love Actually, a surprisingly endearing, yet overstuffed holiday film. Written by Curtis, it was also the first film he stepped behind the camera for, earning his first directing credit. The result is a lovesick mess that has plotlines all over the place: a man who loves his best friend’s new wife, a writer who falls in love with his Portuguese housekeeper despite a language barrier, a man who considers cheating on his wife, the prime minister’s eye on an assistant, a tween who pursues his first love with the help of his stepfather, a woman who cannot risk leaving her sick brother unattended, and a twenty-something Brit who flies to America believing that American girls are easier. And there are a few more. But, look closely – surprisingly few of these stories end happily. Somehow, stuffed with oodles of talent, Curtis made this saccharine motion picture work enough to spurn plenty of terrible imitators since.

Greatest Romantic Comedies
Image: Paramount Pictures

16. Sixteen Candles (1984)/Pretty in Pink (1986)

How could we split these up? They vary in storylines but are basically the same film. Both feature the 80′s high school rom-com queen, Molly Ringwald. Candles tells the story of Samantha’s (Ringwald) upcoming 16th birthday, while everything terrible that could happen to her, in fact, does. Pink focuses on Andie (Ringwald) as she crushes on one of the rich popular guys, Blane (Andrew McCarthy). Both films deal with high school love and relationships. Both films feature a geeky kid who has eyes on the protagonist (Anthony Michael Hall in Candles; Jon Cryer in Pink). Both films were written by John Hughes. Only Sixteen Candles was directed by Hughes, though he produced both. Between these films, Molly Ringwald cemented her place as the face of teenage love and misery in the 80′s, serving as Hughes’ muse in every facet. Despite the cartoonish qualities of both films, what they manage to say about high school life and how it dominates every aspect of our personalities while we’re there is brutally honest. Still: Duckie is the man.

Breakfast at Tiffany’s (1961)
Image: Paramount Pictures

15. Breakfast at Tiffany’s (1961)

It’s a featherweight film based on a Truman Capote novella that, in retrospect, has one of the most insanely racist characters ever put on film (Mickey Rooney as Mr. Yunioshi). But it’s in the National Film Registry of the U.S. Library of Congress. And, it has Audrey Hepburn’s career-defining role, which brought her a fourth Oscar nomination, as Holly Golightly, in the Blake Edwards directed Breakfast at Tiffany’s. The film centers around Holly, a socialite in New York City who begins to fall for a new neighbor in her apartment building. It doesn’t really go anywhere, but the interplay between Hepburn and her co-star George Peppard drives the entire film, as Hepburn switches between a confident party-goer and nervous wreck between her two worlds: the public one and the private one. But somewhere, in all this silliness, Hepburn gives the world one beautifully memorable scene, strumming her guitar and singing “Moon River,” a song written specifically for her vocal range. Regardless of the rom-com traps and the insensitive nature of some of the film, that scene alone and the endearing image of Hepburn, cigarette holder in hand, makes this iconic film a keeper.

Greatest Romantic Comedies
Image: Columbia Pictures

14. Tootsie (1982)

Dustin Hoffman had already built up a stellar career by 1982, nominated for four Oscars, winning one (Kramer vs. Kramer). But he had yet to perform in a film clearly branded as a comedy. The best way to be funny – dress in drag, right? In Tootsie, Hoffman stars as Michael Dorsey – a notoriously difficult actor who can’t get another job. When told he has no chance of being hired again, he decides to go to the extreme:  disguise himself as a woman and audition for a soap opera. Now Dorothy Michaels, he not only wins the part, but finds a way to grow as a man, ironically while being a woman. As Dorothy, Hoffman gets caught up in a twisted love triangle (almost rectangle), where he falls in love with co-star (played by Jessica Lange), her father begins to pursue him/her, another co-star falls in love with him/her, and so on. All the while, Hoffman’s roommate is played by a young, snarky Bill Murray, serving as the audience’s eyes and ears through this ridiculous premise. Above all the crazy twists, Tootsie exposes the inherent sexism found in the system and the extremes it might take for some of our stupidest men to understand how to treat women and, in turn, be worthy of them.

The Princess Bride - Greatest Romantic Comedies
Image: 20th Century Fox

13. The Princess Bride (1987)

The original romantic comedies were probably the fairy tales we all know and love. Well, the PG versions of them, anyway. In 1987, director Rob Reiner collaborated with author/screenwriter William Goldman to present The Princess Bride to the world. A fantasy/adventure/romantic comedy, the film stars Robin Wright as the title character Buttercup, with Cary Elwes playing her lost love Westley. Similar to Robin Hood in many ways, The Princess Bride centers around the princess’ love for Westley, despite his social status, only to see him banished from the kingdom. What results is Westley’s undying attempts to return to her, defeating a Sicillian (Wallace Shawn), joining forces with a pair of outlaws (Mandy Patinkin and Andre the Giant), and crossing paths with other fascinating characters. Delivered as a bedtime story a grandfather (Peter Falk) tells to his son (Fred Savage), The Princess Bride has the kind of slick humor and movie magic that has made it a cult favorite since its original release.

His Girl Friday (1940) - Greatest Romantic Comedies
Image: Columbia Pictures

12. His Girl Friday (1940)

Romantic comedies don’t talk much faster than this one, that’s for sure. Based on the play The Front Page, written by Ben Hecht and Charles MacArthur, His Girl Friday follows newspaper editor Walter Burns (Cary Grant) as he does everything in his power to keep his best reporter from getting married and leaving the paper. The catch: the reporter is Hildy Johnson (Rosalind Russell), his ex-wife. This screwball comedy has plenty of twists and turns, some of which involve her future husband Bruce (Ralph Bellamy), Bruce’s mother, and the city mayor. Directed by Howard Hawks – the king of screwball comedy in the 30′s and 40′s – His Girl Friday set the standard for future offerings in the genre, as its quick-talking dialogue and clever screenplay managed to run circles around the competition. Every character is quick-witted, interesting, and funny, while the story leads to the obvious, yet still satisfying ending.

My Big Fat Greek Wedding (2002)
Image: IFC Films

11. My Big Fat Greek Wedding (2002)

Pop quiz: what’s the highest-grossing film never to reach #1 at the box office? This little independent gem, produced by Tom Hanks and Rita Wilson. My Big Fat Greek Wedding stars (and is written by) Nia Vardalos as Toula, a middle-aged woman who lives in Chicago and can’t escape her very loud and very Greek family. Enter Ian (John Corbett), a non-Greek who she finds herself falling in love with behind her family’s back. In a world of over-the-top comedies where someone’s family is standing in the way of happiness, this one manages to find a way to deliver tons of heart, while shaping all the relatives individually into interesting characters. All our families are crazy. Toula’s may be the craziest, but it’s all out of love: love for her, love for the family, love for their culture, and love for what the ones who came before them have done to make the lives they have now. Love is an international language, after all.


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.

Greatest Romantic Comedies
Image: United Artists

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 it is certainly as funny. Besides, nobody’s perfect.

Pretty Woman (1990)
Image: Buena Vista Pictures Distribution

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.

Bringing Up Baby (1938)
Image: RKO Radio Pictures

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 to 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.

The Graduate (1967)
Image: United Artists

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?

Greatest Romantic Comedies
Image: United Artists

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.

City Lights (1931)
Image: United Artists

5.  City Lights (1931)

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 contain 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.

When Harry Met Sally… (1989)
Image: Columbia Pictures

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 is 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.

Annie Hall (1977)
Image: United Artists

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.

It Happened One Night (1934)
Image: Columbia Pictures

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.

The Philadelphia Story (1940)
Image: Loew’s, Inc.

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.

– Joshua Gaul


Editor’s Note: This article was originally published under our old brand, Sound On Sight.

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