Movies  |  Lists

The 50 Best Romantic Comedies of All Time

April 30, 2013  |  12:37pm
The 50 Best Romantic Comedies of All Time
Our list ranges in date from 1934’s It Happened One Night to 2012’s Silver Linings Playbook, covering every decade in between. We only included films where the romance was central to the plot and that we felt were truly funny—whether the dark comedy of Harold and Maude or the slapstick of The Princess Bride. That means that some classic romances like An Affair To Remember and some gut-busting comedies like Bridesmaids got left off (but you should watch them both anyway).

pretty-in-pink.jpg
35. Pretty in Pink
Year: 1986
Director: John Hughes
Let’s ignore the fact that she ends up with the wrong guy in the end (Team Duckie for life!) and examine what makes Pretty in Pink’s Andie so impossibly cool: She works in a record store and has killer taste in music. Her outfits are daring and incredible. She brushes off insults from evil richie-rich Steff (James Spader) like they ain’t no thang. She supports her deadbeat dad and essentially serves as head of their household. But most importantly, she’s the picture of courage, staying true to herself the whole way through and never changing to please Blane and his wealthy friends—and if there’s any single movie character teen girls should be modeling themselves after as they attempt to swim the treacherous waters of high school without drowning, she’s the one.—Bonnie Stiernberg

groundhog-day.jpg
34. Groundhog Day
Year: 1993
Director: Harold Ramis
Bill Murray, director/co-writer Harold Ramis and screenwriter Danny Rubin take a Twilight Zone-esque comedic premise—a self-centered weatherman gets stuck experiencing February 2 again and again—and find unexpected profundity. A more conventional film would have love resolve the chronological predicament, but instead, it falls to Murray to become the best man he can possibly be. A Hollywood comedy that challenges middle-class Americans to better themselves, Groundhog Day doesn’t just elicit laughs, but leaves audiences more deeply moved than they ever expected.—Curt Holman

jerry-maguire.jpg
33. Jerry Maguire
Year: 1996
Director: Cameron Crowe
Besides acting as the megahit blockbuster of 1996, Jerry Maguire also quickly achieved the status of the modern day romantic-comedy done right. Certainly, between Say Anything and Almost Famous, writer/director Cameron Crowe has never been one to hide his inner softie. Jerry Maguire is no different, featuring career-best performances from Tom Cruise, Renee Zellweger and Cuba Gooding Jr. as well as litany of memorable lines still quoted to this day. And, let’s face it, whoever doesn’t get at least a little bit teary-eyed when Renee Zellweger proclaims, “You had me at hello,” is probably a Cylon spy who should be blasted away at once.—Mark Rozeman

african-queen.jpg
32. The African Queen
Year: 1951
Director: John Huston
The madcap, screwball comedies of the ‘30s and ‘40s helped set the template for the battle-of-the-sexes comedies that would populate American cinemas for years to come (and still do, to some extent). Writer/director John Huston’s genius in making The African Queen was taking the feuding couple out of the metropolitan areas for which they’d often been associated with and instead placing them square in the middle of an inhospitable jungle. With the added element of survival driving their journey, the flirtatious banter between classy widow Rose Sayer (Katherine Hepburn) and crass boatman Charlie Allnut (Humphrey Bogart) crackles all the more, making for a rom-com as vicious as it is sweet.—Mark Rozeman

wall-e.jpg
31. Wall-E
Year: 2008
Director: Andrew Stanton
Before you cry foul, let’s think about the plot of Wall-E for a second: lonely boy meets girl, falls in love, and chases girl to the ends of the earth—or, in this case, the universe. How is that not a romantic comedy? Nevermind they’re robots. Nevermind the lack of dialogue. Nevermind it’s animated. When Wall-E and Eve dance together in the sky amongst the stars, we might as well be watching the second coming of Fred Astaire and Ginger Rogers.—Jeremy Medina

wedding-banquet.jpg
30. The Wedding Banquet
Year: 1993
Director: Ang Lee
Ang Lee’s sophomore feature The Wedding Banquet is an unorthodox rom-com in that it’s not so much about the forming of a relationship as it is about covering up an existing one. Wai-Tung is a gay man living happily with his partner in Manhattan. Due his parent’s conservative nature, he has yet to inform them of his sexuality. As such, they continually badger him to marry a girl and settle down. In an attempt to kill two birds with one stone, Wai-Tung decides to marry his neighbor Wei Wei, a poor artist from mainland China in desperate need of a green card. Besides allowing Wei Wei to stay and work in the U.S., Wai-Tung also hopes to finally get his parent;s off his back. This plan backfires, however, when his parents arrive from Thailand with the intention of throwing him an elaborate wedding. A film that mixes madcap comedy with poignant domestic drama, The Wedding Banquet may not be a conventional romantic comedy, but it certainly stands as one of the best.—Mark Rozeman

waitress.jpg
29. Waitress
Year: 2007
Director: Adrienne Shelly
Every bit as comforting as the delicious, candy-colored pies Keri Russell bakes in the film, Waitress is a honeyed little comedy that should speak to anyone who has ever felt stuck in a situation. And as good as Russell is, the film’s true star is its writer/director/co-star, the late Adrienne Shelly. Murdered before the film saw its release, the film stands as a wonderfully bittersweet testament to her considerable talent.—Jeremy Medina

sleepless-seattle.jpg
28. Sleepless in Seattle
Year: 1993
Director: Nora Ephron
Sleepless in Seattle is essentially one giant love letter to 1957’s An Affair to Remember from writer/director Nora Ephron. Rita Wilson gives a memorable teary summary of the movie, and Annie (Meg Ryan) watches it before writing to Sam (Tom Hanks) inviting him to meet her at the top of the Empire State Building—the way Cary Grant and Deborah Kerr attempt to in their movie—on Valentine’s Day. When they finally meet on the observation deck, the theme from An Affair to Remember swells, setting the mood for anyone with an appreciation for good rom-coms.—Bonnie Stiernberg

juno.jpg
27. Juno
Year: 2007
Director: Jason Reitman
Much has been made about the Diablo Cody-isms that permeate the script, but the heart of Juno is Ellen Page, and her coming to terms with her feelings for Michael Cera. Sure, it takes getting pregnant for her to realize the man of her dreams is the wimp in yellow shorts, but then, the characters in Juno aren’t like normal people anyway. Page’s heavy-lifting deserved every bit of that Oscar nomination.—Jeremy Medina

purple-rose.jpg
26. The Purple Rose of Cairo
Year: 1985
Director: Woody Allen
Allen has stated a number of times The Purple Rose of Cairo is among his favorite films he’s directed, and it’s no wonder—it’s his sweetest and most imaginative film to date. Mia Farrow delivered her best performance in the 13 films she made with Allen, playing a lonely woman who escapes to the movies to live out her fantasies through her favorite actors. Even when the dashing Tom Baxter (a young Jeff Daniels) steps out of the screen and into her life, she keeps her emotions and expectations in check: “I just met a wonderful new man. He’s fictional, but you can’t have everything.” Purple Rose whimsically builds toward a gut-wrenching, elegiac final shot that reminds us why we go to the movies in the first place: to dream.—Jeremy Medina

silver-linings.jpg
25. Silver Linings Playbook
Year: 2012
Director: David O. Russell
With leads as winning as Cooper and Lawrence, and Russell’s signature mix of clever and sincere dialogue, the hook is set. Every single detail doesn’t gel—Chris Tucker’s role as Danny, Pat Jr’s escape-prone friend from the treatment facility, seems a bit extraneous—but it doesn’t need to. By the end of the dance competition finale (yeah, there’s that), the audience, actors and director are on exactly the same page—and it’s Russell’s playbook.—Michael Burgin

bringing-up-baby.jpg
24. Bringing Up Baby
Year: 1938
Director: Howard Hawks
The textbook example of a screwball comedy, Bringing Up Baby finds Cary Grant’s hilariously uptight paleontologist Dr. David Huxley struggling to keep his life together when the flirtatious agent of chaos that is Katherine Hepburn’s Susan Vance comes crashing into his life. Add in shenanigans involving a baby leopard, a collapsing brontosaurus skeleton and some deftly executed pre-MPAA sexual innuendos and you have not only one of the best romantic comedies of all time but one of the funniest American movies ever made.—Mark Rozeman

500-days-summer.jpg
23. (500) Days of Summer
Year: 2009
Director: Marc Webb
“This is a story of boy meets girl. But you should known in advance, this is not a love story,” intones the voiceover at the start of this bittersweet romantic comedy. True to those words, what unfolds is not quite the light, sunshine-y narrative indicated by the film’s vibrant color spectrum. Subverting notions of the typical rom-com, Summer acknowledges the all-too-true notion that sometimes, without definite rhythm or reason, a relationship can just not work out—no matter how badly you want it to. The film’s non-linear structure — which jumps back and forth across the titular 500 days between the couple’s initial meeting, their breakup and the point where lead character Tom (Joseph Gordon-Levitt) can finally move on with his life — helps to emphasize the delicate nature of romantic relationships and how perception means everything. Speaking of perception, who hasn’t been in the position so accurately displayed in the film’s devastating “Expectations vs. Reality” sequence?

his-girl-friday.jpg
22. His Girl Friday
Year: 1940
Director: Howard Hawks
Adapted from the widely acclaimed play The Front Page, His Girl Friday is a classic whose sharp, witty dialogue matches that of old newsrooms. This smooth-talking editor, played by the always-charming Cary Grant, recognizes true journalistic talent and goes to great lengths to get his best reporter to cover a major story.—Bonnie Stiernberg

the-graduate.jpg
21. The Graduate
Year: 1967
Director: Mike Nichols
In the undisputed king of movies for those headed out into the real world, a hyper-accomplished recent grad (Dustin Hoffman) panics at the prospect of his future and falls into an affair with the much older wife of his father’s business partner (Anne Bancroft). It helped define a generation long since embalmed by history, but the sense of longing for an alternative hasn’t aged.—Jeffrey Bloomer

comments powered by Disqus
Related
Load More