Top 10 Romantic Comedies of All-Time

With the month of February being home to Valentine’s Day, the entire month’s “What the Hell Were They Thinking?!” and “Benjamin’s Stash” segments were devoted to some of the best… and some of the worst rom-coms out there. Now with February behind us, it’s time to cap things off with a look back at the top 10 very best of the best cinematic odes to love, dating, marriage and happily ever afters. They make you laugh; they make you cry; and they melt your heart into butter.

Well, figuratively speaking, that is… otherwise, please, consult your doctor.

First off, parameters need to be set as to what is going to be considered a romantic comedy by this list. This turned out to be a pretty hard list to come up with not only due to how many great films there are in just a sub-genre of the much wider-encompassing genre that is romance, but also due to debating on whether or not some films should actually be classified as a rom-com. The Princess Bride, for example, is certainly funny and has romance; however, I classify that film more as a fantasy adventure that has humorous and romantic ingredients baked within it. Eternal Sunshine of the Spotless Mind has moments of levity and Charlie Kaufman/Michel Gondry’s trademark quirkiness, but that’s more a poignant statement on relationships and heartache with a sci-fi twist. Groundhog Day comes close to rom-com territory, but the relationship that eventually develops between Bill Murray and Andie MacDowell is more a byproduct of the main character’s central conflict to stop being a self-absorbed dick to everyone and become a better man.

Bottom line: to qualify here, it obviously must be a comedy (or dramedy), the comedy must be drawn from tension in the film’s key romantic relationships, and the relationships also must be central to the main characters’ journey throughout the story.

Or I could’ve just said, my site, my rules… deal with it, people.

Hey, sometimes the thug life chooses you, you don’t choose it.

So before we before fall head over heels and straight into the arms of this top ten list, let’s quickly run through some honorable mentions that almost made the cut…

500 Days of Summer, Amelie, The Big Sick, Bringing Up Baby, Chasing Amy, Crazy Rich Asians, Forgetting Sarah Marshall, Four Weddings and a Funeral, High Fidelity, Knocked Up, L.A. Story, Manhattan, Punch-Drunk Love, Roman Holiday, Say Anything…, Silver Linings Playbook, There’s Something About Mary, Tootsie, Working Girl and You Can’t Take It with You.

With all that said and out of the way, as Marvin Gaye once said, let’s get it on… with this list, I mean.

10) Moonstruck (1987)

C’mon, if you actually thought this film wasn’t gonna make the cut, well then, SNAP OUT OF IT! Led by two great performances from Academy Award winners Nicholas Cage and Cher, who’d win a Best Actress Oscar for her performance, Moonstruck follows an Italian-American widow who gets engaged again only to – yikes! – fall for her fiance’s hot-tempered and handless younger brother. And who better to play someone that’s both hot-tempered and handless than an eccentric loose-cannon like Cage? Director Norman Jewison deftly balances the offbeat, screwball energy with Oscar-winning writer John Patrick Shanley’s poignant observations on love, relationships and infidelity with nary a single misstep, and all while tracking multiple relationships in a manner that never loses focus or feels overcrowded. Of course, to keep thing alive and engaging, it helps that you have Cher and Cage’s main relationship backed up by Shanley’s wonderfully drawn ensemble of supporting characters played by Oscar nominees Danny Aiello, Vincent Gardenia and Olympia Dukakis, who like Cher would also go on to win Best Supporting Actress for her performance.

9) Bull Durham (1988)

“Well, I believe in the soul, the cock, the pussy, the small of a woman’s back, the hanging curve ball, high fiber, good scotch, that the novels of Susan Sontag are self-indulgent, overrated crap. I believe Lee Harvey Oswald acted alone. I believe there ought to be a constitutional amendment outlawing Astroturf and the designated hitter. I believe in the sweet spot, soft-core pornography, opening your presents Christmas morning rather than Christmas Eve and I believe in long, slow, deep, soft, wet kisses that last three days.”

Yes, I know. It’s the dreaded love triangle, but writer/director Ron Shelton eases any apprehensions you might have of sitting through all those annoying trappings of the device by focusing first and foremost on his characters. Led by three top of their game performances from Academy Award winners Kevin Costner, Susan Sarandon and Tim Robbins, Bull Durham follows Sarandon’s Annie, a baseball enthusiast with a thing for minor-league prospects, who winds up catching both Costner and Robbins in her sultry little web. Providing sharp insight on both very-much complicated relationships and the inside details of baseball, the film is able to double as both an excellent romantic comedy and an excellent baseball flick. Who knew a filmmaker coming straight out of the world of minor-league baseball would seem to know more about love and relationships than Nicholas Sparks and most rom-coms today?

8) It Happened One Night (1934)

You’ll never be able to read about Joshua facing off against the “walls of Jericho” the same again after seeing this little Oscar-winning charmer, the first to win the “Big Five” at the Academy Awards (Best Picture, Director, Actor, Actress, and Adapted Screenplay). Generally considered by many to be the OG of major rom-coms, It Happened One Night centers on a newlywed spoiled heiress’s road trip with a cynical reporter who’s helping her reunite with her new husband in return for an exclusive story, but along the way, more sparks may end up flying between them than either would’ve anticipated at the beginning. While that premise has certainly been aped to death since its release nearly 90 years ago, this film benefits supremely by rom-com extraordinaire Frank Capra’s light and breezy directing touch and the dynamic chemistry between Clark Gable and Claudette Colbert, with Gable dialing the charisma up to a thousand. In fact, Gable’s onscreen magnetism is so all-powerful here, just a small simple move of him removing his shirt to reveal nothing more than his bare-naked chest single-handedly killed the undershirt business, and it took something as drastic as an entire World War to bring it back. Yes, the legendary actor may, understandably, be more remembered for Gone with the Wind, but his comic charm has never been better than it is here, particularly during one of the film’s most memorable moments where he hilariously explains to Colbert the differences in how men get undressed while detailing his own sequence, before finally getting to just the pants and “it’s – uh – every man for himself”.

Also, between those two films of his, what’s this guy’s deal with spoiled chicks?

7) His Girl Friday (1940)

What’s a top rom-com list without Cary Grant? One could easily make a top rom-com list just going solely by his own filmography, and His Girl Friday ranks as one of the very best. As hard-boiled editor Walter Burns, Grant learns that his fetching ex-wife and ace reporter, played by the lovely Rosalind Russell, is newly engaged to – dear God! Ralph Bellamy?! And, quite frankly, Grant will be damned if he’s gonna just sit back and allow that to happen, as he entices her with one last story while he attempts to sabotage the engagement. To say Grant and Russell’s onscreen chemistry is dynamite is an understatement as they light up the screen together, with director Howard Hawks having them speed-up the delivery of their overlapping dialogue to make their sparks-filled, biting barbs hit each other like machine-gun fire. Of course, in true Cary Grant fashion, a good deal of his dialogue was ad-libbed, including the infamously hysterical ribbing of Ralph Bellamy’s character by meta-name-dropping the actor’s real name, which reportedly pissed off the studio heads until Hawks was able to convince them to keep it in. Even beyond the rom-com genre, the film’s speedily-paced banter would go on to influence fast-paced, rapid-fire efforts from filmmakers such as Robert Altman and the Coen brothers to TV shows such as The West Wing, Gilmore Girls and Veep.

6) When Harry Met Sally (1989)

“I’ll have what she’s having.”

I bet you will, Mrs. Rob Reiner’s mom. When it comes to the ’80s, Reiner’s work as a director is somehow, inexplicably overlooked and criminally so. We’re talking about one of the greatest mockumentaries with This Is Spinal Tap, one of the greatest coming-of-age films with Stand By Me, one of the greatest fantasy adventures with the aforementioned The Princess Bride, and here, one of the greatest, most quotable rom-coms to ever win over viewers’ hearts. Penned by the late, queen of rom-coms Nora Ephron (who’d score a Best Original Screenplay Oscar nod for this script), When Harry Met Sally boasts Ephron’s sharp writing, Reiner’s sure-handed directing touch, a couple fine supporting turns from Carrie Fisher and Bruno Kirby, and 100% on-point chemistry from Billy Crystal and the adorable Meg Ryan. And, of couse, there’s the deli scene, which has gone down in rom-com history as one of the funniest and most iconic scenes ever, not just for Ryan’s gung-ho, go-for-broke performance, but also for the subtly awkward touches in Crystal’s reaction. Yes, since the film’s release, every rom-com and its brother has copied its formula ad nauseam. Whether it’s the meet-cute or the late-night holiday admission of love, they’ve all beaten those tropes to death so hard it’s now almost starting to border on parody. Still, that takes nothing away from this rom-com gem, and as the saying goes, “Often imitated, never duplicated.”

5) The Apartment (1960)

It’s a shame that a lot of viewers from my era and after seem to only recognize two-time Oscar winner Jack Lemmon as the crotchety old guy in the Grumpy Old Men films and Out to Sea. Dive a little further back, and you’ll see that he was more than just a grumpy caricature and was a legit, award-level actor in a number of fantastic films. The Apartment sits right at the top of the list as one of his best. Lemmon plays “Bud” Baxter, an insurance agent hoping to climb the corporate ladder by lending his apartment out to his boss for his extramarital affairs, only to find out the office’s elevator operator he secretly pines for, played by Shirley MacLaine, is having her own affair with his boss. Laced with Oscar-winning filmmaker Billy Wilder’s trademark biting cynicism, The Apartment is equally as tragic as it is funny and charming, and you probably won’t find a bleaker film on this list. I mean, how many rom-coms can boast multiple suicide attempts? Still, don’t let the bleakness turn you off, ’cause at the film’s core is the tender bond that forms between Bud and MacLaine’s Fran, with the Oscar-winning legends making for an extremely sweet onscreen pair, and Wilder’s bittersweet edge at least culminating on a rather hopeful note.

Also, this may not be the last time you see both Jack Lemmon and Billy Wilder together on this list.

4) Broadcast News (1987)

“Wouldn’t this be a great world if insecurity and desperation made us more attractive? If needy were a turn-on?”

Hey, look! Another love triangle! Broadcast News is easily three-time Oscar winning writer/director James L. Brooks’s best film, which says something when Terms of Endearment, As Good As It Gets and Spanglish are no slouches either. Like Bull Durham did for baseball, this workplace rom-com provides keen, behind the scenes insight into the world of TV journalism, with Academy Award winners William Hurt, Holly Hunter and Academy Award nominee Albert Brooks turning out some of the best performances of their storied careers. Sure, it’s a familiar plot device – career girl is stuck in between the hunky but dense newsman and her intelligent but prickly longtime coworker/friend. However, the late, great Hurt, Brooks and a wonderfully spunky and energetic Hunter infuse what might seem like character stereotypes on paper with such vitality and James L. Brooks delivers colorful dialogue that’s at the top of his game. The ending may not necessarily be the happy one hopeless romantics might prefer, but it’s one that nevertheless rings achingly true.

3) The Philadelphia Story (1940)

Ooh! It’s another love… pentagon? You’ll get it when you see it. Long before Owen Wilson and Vince Vaughn made it cool, Cary Grant and Oscar-winner James Stewart (who won Best Supporting Actor for his performance here) played the original wedding crashers, as Grant’s C.K. Dexter Haven conspires with Stewart’s tabloid journalist Mike Connor to crash the wedding of Haven’s ex-wife played by four-time Academy Award winner Katherine Hepburn. Ruth Hussey (who would earn a Best Supporting Actress nod for her performance) and John Howard provide great support that rounds out the pentagon, but of course, the spotlight is on Grant, Hepburn and Stewart. Their chemistry is intense enough to catch fire and it’s simply just a joy to watch these three all-time great acting legends go toe-to-toe against each other while rattling off Donald Ogen Stewart’s whip-smart, biting, class war-targeting back-and-forths. It’s shocking to think that for a brief period of time prior to this, despite already having won her first Oscar, Hepburn was labeled as box office poison after a string of commercial failures (including the honorably mentioned Bringing Up Baby opposite Grant), yet this film completely shattered that label, and for good reason. Drawing the attention of not just one, nor two but three suitors vying for her affection, Hepburn absolutely steals the show with what is arguably the finest performance of her long and illustrious acting career.

2) Annie Hall (1977)

Star Wars fanboys will forever disdainfully view this film as “the one that beat their beloved, hallowed classic for Best Picture“. Now, I could rile them up even further by saying out of the two major sci-fi flicks released in 1977, Close Encounters of the Third Kind should’ve taken that nomination from it. Regardless, Annie Hall is, without a doubt, Woody Allen’s best film, one that radically revolutionized what would become the modern romantic comedy and would go on to inspire offbeat hits of the genre such as When Harry Met Sally; Definitely, Maybe and 500 Days of Summer, among many others. The supporting cast is amazing, as is par the course for most of Allen’s films, and Diane Keaton’s Oscar-winning turn is the best of her career (which says something when you also have fantastic work in The Godfather franchise listed on your resume). As with most of Allen’s films, though, the true star is, of course, the writing, with Allen putting together a brilliant and wholly unconventional deconstruction of the genre that examines the rise and fall of a relationship in his own hilariously absurd and neurotic way. But underneath all the filmmaker’s trademark unorthodoxy and absurdist humor is a rather poignant story that paints an emotionally honest portrait of falling in… and then out of love.

Okay, readers, we’ve finally made it to the #1 spot. And the winner is… The Hottie & the Nottie. Paris Hilton… what a delightful charmer… Okay, let’s try this again.

Drum roll, please…

1) Some Like It Hot (1959) 

“Look at that! Look how she moves. That’s just like Jell-O on springs.”

Screwball comedy at its absolute, pitch-perfect best, Some Like It Hot stars Tony Curtis and Jack Lemmon as two Chicago musicians who disguise themselves as women and join an all-female band in order to escape the mob after witnessing a crime. Buuuut then things get even more complicated for the two when they both fall for the band’s voluptuous vocalist/ukulele player Sugar Kane and begin competing for her affection, all while still maintaining the disguise. Both Lemmon and Curtis display impeccable comedic timing together, and the blonde bombshell above all blond bombshells that is the late Marilyn Monroe is delightfully bubbly as the ultimate romantic foil. Writer/director Billy Wilder dials the madcap energy all the way up to the max and produces a number of hysterical role-reversal sequences that isn’t as shy toward its subject matter as you might expect a film from the ’50s to be. And then that ending. Yes, that gut-bustingly hysterical ending is one of the greatest endings of any movie period, closing itself out with what one could say is the “perfect” punchline.

Well, there you have it, readers! The very best of the best silver screen tributes to both love and laughter. For those that are beyond indignant that All About Steve or Good Luck Chuck didn’t make the cut, feel free to send all hate mail and (or) death threats to the email provided in the contact section. For the rest of you, feel free to let me know what some of your all-time favorite romantic comedies are in the comments.

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