Of course, "When Harry Met Sally" also owed a debt of influence to Woody Allen's romantic comedies about talky New Yorkers, as well as to dozens of other rom-coms, going all the way back to the road-trip antics of Clark Gable and Claudette Colbert in 1934's screwball classic, "It Happened One Night."
There are a lot of great romantic films that go to such dark places (from "The Apartment" to "Eternal Sunshine of the Spotless Mind") that I'm not sure they qualify as comedies. Others, particularly in recent years, make me despair that no one knows how to write a good romantic comedy anymore. But there are some gems, films viewers keep turning to over and over, whenever they want to laugh and to fall in love vicariously all over again.
Gallery | The Best Romantic Comedies Ever Made
- 37. 'Pretty Woman' (1990)
Everyone's favorite modern Cinderella story started out as a much darker drama. Really, there's no reason this tale of a Wall Street buccaneer and a Hollywood streetwalker should have worked, but for director Garry Marshall's blithe tone and the undeniable charisma and chemistry of veteran charmer Richard Gere and vivacious then-newcomer Julia Roberts.
- 36. 'My Big Fat Greek Wedding' (2002)
Nia Vardalos penned for herself the role of a lifetime as the shy travel agent who blossoms when she meets Mr. Right (John Corbett), who, in turn, is amused to learn that, when you marry a Greek woman, you marry her whole clan. Anyone who's ever faced the culture shock of assimilation-by-marriage can appreciate this film.
- 35. 'Sleepless in Seattle' (1993)
Tom Hanks and Meg Ryan had already worked together in the oddball "Joe vs. the Volcano," and they would again in "You've Got Mail," but here, they have such chemistry that they seem like a couple even though they don't meet until the end of the film. Nora Ephron's film is a witty exploration of the difference between real-life love and love as the movies have sold it to us.
- 34. 'Amelie' (2001)
Audrey Tautou's starmaking role came in this thoroughly inventive French comedy about a young woman so intent on brightening the lives of others that she doesn't notice when she herself stumbles into romance.
- 33. 'Wedding Crashers' (2005)
Romantic cynics Owen WIlson and Vince Vaughn find their respective matches in fresh-faced Rachel McAdams and mischievous nymphomaniac Isla Fisher, but the movie is as much about the ups and downs of the guys' bromance as love comes between them.
- 32. 'The Lady Eve' (1941)
- 31. 'The Wedding Banquet' (1993)
Ang Lee's early comedy, about a sham green-card marriage that turns real in unexpected ways, explores the borders between tradition and modernity, gay and straight, male and female, and American and Asian manners, and it generously finds much to admire on all sides.
- 30. 'The Wedding Singer' (1998)
Drew Barrymore and Adam Sandler have paired twice more since this landmark hit, but there's no topping their original romance as a couple who find love in a New Jersey catering hall. Barrymore is as winning as ever, but it's Sandler, whose man-child shtick is for once more sweet than abrasive, who makes it work.
- 29. 'Honeymoon in Vegas' (1992)
Most romantic comedies end with one partner (usually the guy) making a grand, foolish gesture to prove his love. Well, as Nicolas Cage discovers, romantic gestures don't come grander than dressing in an electrically-illuminated Elvis costume and jumping out of a plane.
- 28. 'Sixteen Candles' (1984)
The archetypal teen movie of the 1980s is also the decade's archetypal rom-com. Making his directing debut, screenwriter John Hughes is a lot more generous to all his characters here than he will be in later films ("Home Alone"). It's not just Sam (an earnest Molly Ringwald) but everyone, beautiful people and nerds, to end up right where they deserve.
- 27. 'Roxanne' (1987)
This update of "Cyrano de Bergerac" features Steve Martin at his most graceful as a big-nosed firefighter who's too shy to woo his crush (Daryl Hannah) but feels free to express himself when his handsome colleague (Rick Rossovich) is the mouthpiece.
- 26. 'The 40-Year-Old Virgin' (2005)
Behind all the raunch of Steve Carell's belated quest to lose his virginity, there's actually a sweet love story between Andy (Carell) and Trish (Catherine Keener), the woman who gently coaxes him into maturity. Director Judd Apatow sets the tone for a future slate of comedies about bros who need to grow up in order to deserve the desirable women who are (miraculously) willing to put up with them.
- 25. 'The Sure Thing' (1985)
Rob Reiner's update of "It Happened One Night" has college students John Cusack and Daphne Zuniga falling for each other during a cross-country road trip and discovering (as college students often do) that what they thought they wanted isn't what they wanted at all. There's a direct line from Cusack's surprisingly sweet horndog here to his boombox-lifting serenader Lloyd Dobler in "Say Anything" and his reign as Gen X's favorite romantic leading man.
- 24. 'Scott Pilgrim vs. the World' (2010)
With its flashy comic book/video game-inspired visuals and wispy young rom-com hero (Michael Cera), Edgar Wright's epic of youthful romance was a movie I expected to loathe as shallow and superficial. Unfortunately, I then saw the movie and realized Edgar Wright's attempt to forge a new visual language for the expression of romantic moments on screen was actually pretty brilliant. Damn.
- 23. 'What's Up, Doc?' (1972)
Peter Bogdanovich updates "Bringing Up Baby" and (as the title suggests) infuses it with the fizzy slapstick energy of a Bugs Bunny cartoon. Ryan O'Neal has Cary Grant's role as the uptight scholar; Madeline Kahn makes a scene-stealing debut as the all-wrong-for-him fiancee; and Barbra Streisand shows off her comedy chops as the loose cannon who sets her sights on O'Neal.
- 22. 'L.A. Story' (1991)
Steve Martin pokes fun at Hollywood shallowness even while finding the City of Angels an inspirational, even magical place to fall in love. Bonus points for casting Sarah Jessica Parker in a starmaking supporting role that saw her transformed from nerdy, '80s Square Peg into a sexy romantic-comedy sprite.
- 21. 'The Philadelphia Story' (1940)
More breezy fun from Katharine Hepburn, as a snooty heiress, and Cary Grant, as the ex-husband who won't go away, plus wild card Jimmy Stewart, as a gossip reporter who learns too late that he's in way over his head.
- 20. 'Roman Holiday' (1953)
- 19. 'Seven Chances' (1925)
Buster Keaton stands to inherit a fortune if he gets married -- by the end of the day. Romantic mishaps with his sweetheart force him to look elsewhere, leading to the film's climactic spectacle of Keaton being chased through the streets of Los Angeles by five hundred would-be brides. Proof that you didn't need sound to make a laugh-out-loud romantic comedy.
- 18. 'Bridget Jones' Diary' (2001)
Renee Zellweger brings to vivid and hilarious life Helen Fielding's blundering British bachelorette. Hugh Grant brilliantly channels his inner cad as the bad boy who tempts Bridget, while Colin Firth channels his own "Pride and Prejudice" performance to play a Darcy who's sour exterior masks his love for the exasperating Bridget -- just as she is.
- 17. 'Harold and Maude' (1971)
Gloomy, suicide-faking 20-year-old Harold (Bud Cort) finds just what he needs in Maude (Ruth Gordon), the world's oldest Manic Pixie Dream Girl. With a six-decade age gap, their romance can't last forever, but she sure does teach him to appreciate life.
- 16. 'Moonstruck' (1987)
Cher won a well-deserved Oscar as a Brooklyn widow who gets engaged to a mama's-boy, only to fall for his hot-tempered brother (Nicolas Cage). John Patrick Shanley's screenplay is full of keepers, especially Cage's speech about how we're here to fall in love with the wrong people, ruin our lives, and die.
- 15. 'Clueless' (1995)
Amy Heckerling was clever to update Jane Austen's "Emma" to a Beverly Hills high school setting, but her smartest accomplishment was casting Alicia Silverstone as the matchmaker heroine who doesn't know her own heart. Paul Rudd's reign as a romantic comedy lead who can strike up chemistry with anyone (from Courtney Love to Michelle Pfeiffer) begins here.
- 14. '(500) Days of Summer' (2010)
Mark Webb tries to update the whole genre with this time-jumping look at the doomed romance between mopey Tom (Joseph Gordon-Levitt) and free-spirited Summer (Zooey Deschanel), and for his creativity, he's punished by being forced to make Spider-Man movies.
- 13. 'Crazy, Stupid, Love' (2011)
In which a group of Angelenos all fall in love with the wrong people but still believe in romance because what else can you do? This should be hangdog Steve Carell's movie, but Ryan Gosling (at his most self-confident) and Emma Stone (at her most adorable) steal it from him.
- 12. 'All of Me' (1984)
Steve Martin gives his most brilliant physical comedy performance as a lawyer who falls for the crabby heiress (Lily Tomlin) whose spirit possesses one side of his body. Sublime and unjustly forgotten.
- 11. 'There's Something About Mary' (1998)
The Farrelly brothers' smash helped make mainstream romantic comedy safe for R-rated raunch, but for all this movie's innovation in bodily-fluid humor ("Is that...hair gel?"), it's actually a rather sweet story about a guy winning back his high-school sweetheart. Cameron Diaz is a sport, but it's Ben Stiller who proves himself a modern-day romantic male lead by being willing to endure any humiliation, no matter how painful.
- 10. 'Four Weddings and a Funeral' (1994)
Hugh Grant became a romantic comedy star in Richard Curtis's farce about a would-be couple suffering from an extended case of very bad timing.
- 9. 'When Harry Met Sally' (1989)
Can men and women ever be truly platonic friends? No? All right, then.
- 8. 'His Girl Friday' (1940)
Not just one of the best romantic comedies, but easily the most fast-talking. In this gender-twisted version of the classic "The Front Page," Cary Grant is a wily newspaper editor who schemes endlessly to make sure his ace reporter (Rosalind Russell) -- who's also his ex-wife - doesn't run off to a life of domestic bliss with her dull new fiance. Really, he's rescuing her from a life of boredom, even if it's for entirely self-serving reasons.
- 7. 'Singin' in the Rain' (1952)
Besides being one of the greatest musicals of all time and one of the slyest satires about Hollywood, the movie also contains at its heart a sweet, funny romance between Gene Kelly and Debbie Reynolds as two actors who must overcome professional pride in order to acknowledge their mutual attraction.
- 6. 'Bringing Up Baby' (1938)
Of the three romantic comedies Katharine Hepburn and Cary Grant made together, this one is the most effervescent, thanks to Hepburn's charm as a daffy heiress, Grant's playing against type as a hapless nerd, and some help from the animal kingdom in the form of a music-loving leopard.
- 5. 'Love Actually' (2003)
After such successes as "Four Weddings and a Funeral" and "Notting Hill," screenwriter Richard Curtis decided to create the rom-com to end all rom-coms, and he arguably succeeded here, with this overstuffed Christmas confection whose multiple couples explore seemingly every kind of love imaginable (including Puppy, Platonic, and Unrequited).
- 4. 'Some Like It Hot' (1959)
Billy Wilder's drag comedy is one of the funniest movies of all time. And no, it's not fair that Tony Curtis (channelling Cary Grant) gets to romance Marilyn Monroe (at her sexiest and not-so-dumb blondest) while Jack Lemmon is stuck with Joe E. Brown.
- 3. 'Tootsie' (1982)
- 2. 'It Happened One Night' (1934)
The film that pretty much invented the romantic comedy as a film genre and wrote all the rules. EIghty years later, Clark Gable and Claudette Colbert remain an irresistible pair (she's a runaway heiress, he's the brash reporter who tails her) and the definition of an all-American, class-defying, resourceful, wisecracking, sexy movie couple.
- 1. 'Annie Hall' (1977)
Woody Allen and Diane Keaton's re-enactment of their off-screen romance is the ultimate romantic comedy because Allen throws every trick in the director's playbook at it in order to explore why we fall in love, why we fall out of it, and why we keep trying. Best of all, it shows how movies can offer us resolution where real-life romances often fail.
Article photo courtesy of Everett