Best Romantic Comedies

Ah yes, the romantic comedy. An oft-mocked genre that tends to rank low on the list of prestige genres. The genres suffers occasional attacks from the right because it apparently glorifies sex while it also has to endure salvos from the left because it paradoxically also seems to entrench regressive gender roles and sexual politics. It is often derisively called a “woman’s genre”, ignored most awards seasons, and seemingly crowded out of our modern uber-blockbuster box office landscape.

And yet to dismiss the genre as a guilty pleasure is an egregious error indeed. While it is true that a bad romantic comedy is a guilty pleasure for some (in the same way bad horror movies are a guilty pleasure for me), there are an incredible number of romantic comedies that are simply truly great movies which hopefully this list will bear out. So here I present what I humbly contend are great movies that simply confirm that the romantic comedy deserves a little bit more respect.

Honourable Mentions:

Bringing Up Baby – Katherine Hepburn and Cary Grant find themselves falling into trouble and then into love as they try to deal with everything from missing dinosaur bones to a leopard named Baby in the classic definition of a screwball comedy.

Juno/Waitress – Both of these are wonderfully warm comedies, but it just seems to me that the movies are much more about the personal growth of the women with their romantic pursuits simply a subplot.

Moonrise Kingdom – Wes Anderson built up his reputation as a great filmmaker by being a strict formalist who approached his subjects with cold detachment. But in Moonrise Kingdom he decides instead to embrace a little warmth and innocence and the end result is a near-perfect depiction of young love.

The Princess Bride – Sometimes love needs to be naive, overly sincere, and extravagantly beautiful with a heavy dash of swashbuckling swagger.

The Big Sick – As a non-white person who got engaged to a white girl during a particularly tumultuous period in my life health-wise it should come as no surprise that I connect to this movie at an almost spiritual level. Also it potentially reveals the path forward for romantic comedies in its earnest embrace of something akin to the mess of reality. But it’s just too new for me to move it up to the big league yet.



10. GROUNDHOG DAY (1993) dir. Harold Ramis

There must be something highly satisfying for women (I imagine) in watching an extremely stubborn man have to relive the same day time and time again until he has been completely broken down enough and had enough of his pride ground out of him to finally admit that he is wrong about the way he has carried his life and treated the people around him. Of course the premise of a man living out Groundhog Day time and time would be played out strictly for slapstick laughs if it were placed in the hands of anybody else but Bill Murray. But as played by Murray, it becomes a frequently profound and melancholic tale about the mediocrities we fall into and a call to better ourselves. Also Andie MacDowell actually is kind of good in this one.


9. THE LADY EVE (1941) dir. Preston Sturges

No list about great romantic comedies would be complete without including the great comedy director Preston Sturges. And any list that doesn’t include a Barbara Stanwyck picture in it is completely illegitimate. Together with Henry Fonda, Stanwyck and Sturgess form a triumvirate that produces comedy gold in The Lady Eve. In a great twist to the formula, Stanwyck plays a beautiful, brash, pushy, and altogether in control con-artist who initially is interested in a naive and sweet Fonda only because she wants to get her hands on his money as an heir to an enormous fortune. Of course because this is a Sturges screwball picture, things quickly spin out of control leading to twists, thrills, laughs, and, like a great Shakespeare comedy, finds space for romance in the midst of it all.


8. THE PHILADELPHIA STORY (1940) dir. George Cukor

Just as a list without Barbara Stanwyck would be illegitimate, a list of romantic comedies without Katherine Hepburn, Cary Grant, or Jimmy Stewart would simply be tragic. And the three of them combined to create wonderful alchemy in The Philadelphia Story, producing an all-time classic. In a fantastic workaround to the stodgy Production Code (which forbade depictions of extra-marital affairs) Hepburn plays a divorced socialite on the eve of her remarriage whose day is complicated by the arrival of her ex-husband (Grant) and a tabloid reporter sent to cover her upcoming nuptials. It is the perfect setup to a movie that holds no surprises as to where the story is ultimately headed but is so much fun to get there.


7. AMELIE (2001) dir. Jean-Pierre Jeunet

It is nearly impossible to find a more charming movie than Amelie. The movie has forced itself into a subtitle-averse North American context and it is mostly on the back of Audrey Tautou as the titular waitress who makes it her chief mission in life to bring happiness to others. Perfectly skirting the line of being quirky without being grating and heartfelt without ever feeling corny or cheesy, the movie is an effortless breeze from beginning to end. And in the hands of the highly imaginative Jeunet, it also becomes a frequent surprising visual delight and a celebration of the innocence of first love. framed by the most romantic city in the world.


6. WHEN HARRY MET SALLY… (1989) dir. Rob Reiner

When Harry Met Sally… is often unfairly lumped into the same class as the mediocre copycats (often starring Meg Ryan) that it helped spawn. However this is an egregious mistake. Boasting one of the best modern screenplays ever written by Nora Ephron, this movie is brimming with witty dialogue that is ably handled by Meg Ryan and Billy Crystal who both produce what is arguably the best performances of their careers. Starring as two sides of a neurotic anti-couple, the movie is notable not just for that deli scene (you know what I’m taking about) but also for being one of the first romantic comedies that dared to write a woman lead as having their worth derived from more than being the object of male desire. It also helps that unlike most romantic comedies, the relationship is one that develops over twelve years where 95% of that time is devoted to finding ways not to fall in love with one another. To quote Roger Ebert in his review, Harry and Sally “fight happiness every step of the way, until it finally wears them down.” And that is what makes it great.


5. HIS GIRL FRIDAY (1940) dir. Howard Hawks

The screenplay looks like it would have enough words for a three-hour epic but somehow it clocks in at 90 minutes. There has probably never been such witty repartee delivered at a faster pace as Cary Grant and Rosalind Russell play a soon-to-be-divorced couple and former coworkers who just can’t quit each other. When Hildy Johnson (Russell), a former ace journalist and ex-romantic partner to hardboiled editor Walter Burns (Grant), shows up on the day of a major execution, Burns manages to entice her into covering one last story which sets off a frantic chain of events. In between there is Hildy’s new fiancee for Walter to try and thwart, an execution to stall, and a frantic matching of wits between Hildy and Walter as they try to outmaneuver the other. It is an altogether exhausting to try and keep up with, but it is also extremely exhilarating.


4. SOME LIKE IT HOT (1959) dir. Billy Wilder

This movie is the prime piece of evidence that Marilyn Monroe, apart from being one of the most beautiful women to ever grace the screen, is also one of its great comic minds. Theoretically Tony Curtis and Jack Lemmon are the main characters of this movie as two hard-on-their-luck musicians who run away from the mob by disguising themselves as women and joining an all-female jazz band, but you wouldn’t know it because Monroe practically steals every scene that she appears in and proving herself more than equal to the comic wits of Curtis and Lemmon. The movie is from beginning to end one of the greatest farces ever put to screen. It is also the movie my wife can hold over my cinephile head for all time as I, in my more naive and pretentious cinephilic days, didn’t want to watch the movie because I thought it was going to be shallow and dumb. And she more that proved me wrong. Lesson learned: always listen to your wife.


3. WALL-E (2008) dir. Andrew Stanton

The undeniable proof that love truly transcends all conventional bounds, this movie about the trash-compacting robot WALL-E who is the last of its kind on an abandoned earth and falls in love with a newly-arrived surveillance robot EVE is as touching and romantic a movie as those starring flesh-and-blood humans. Borrowing straight out of the playbook of great silent romantic movies, the majority of this children’s movie is simply told through bleeps, boops, and anthropomorphic facial expressions and yet so much story, character, and romance is conveyed so well that it puts so many other romantic comedies that have the benefit of human actors and words and yet can’t muster up anything resembling believable chemistry to shame.


2. CITY LIGHTS (1931) dir. Charlie Chaplin

While WALL-E managed to evoke silent comedies of the past, the fact remains that it cannot surpass this great and endlessly charming Chaplin comedy. Chaplin’s comedic and slapstick ability is well-established but in City Lights he combines his nearly unparalleled ability to generate a laugh with an earnest and sentimental tale of love and pathos as affecting as any drama of its time and since. Starring himself as The Tramp he plays a poor and despondent outcast who falls in love with a blind flower girl who mistakes him for a much richer man and he tries his very best, and often fails comically and spectacularly, to maintain that facade. And while the movie is frequently funny, it is its heartwarming emotion that lingers. The final scene of the movie (which I won’t spoil here) is truly one of the great emotional scenes in all of cinema that many have tried to imitate but few have come remotely close to equalling.


1. THE APARTMENT (1960) dir. Billy Wilder

Perhaps this is just evidence of my weird eccentricities but I maintain that “Shut up and deal” is one of the most romantic lines ever delivered. Whenever I revisit this movie I’m always surprised by how melancholic the story is, but that is probably because what we always rightly remember is the effortless charm of Jack Lemmon, as the frequently frustrated coworker who is constantly taken advantage of by his lecherous executives, and the radiant Shirley MacLaine, who has perfects her ability to mask her profound sadness until she can’t anymore. Like The Big Sick would do many years later, The Apartment works powerfully because it doesn’t shy away from the darker tragedies of life but genuinely tries to find some warmth, tenderness, and romance in spite of it. And in the hands of Billy Wilder, the eternal cynic, the movie also successfully mines the absurdity of corporate America for comedic effect in a way that still remains poignant today. But the reason why it is the greatest romantic comedy of all time is because there is hardly a more perfect couple ever depicted onscreen than Jack Lemmon and Shirley MacLaine.

Now shut up and deal. Happy Valentine’s Day.



Final note: You will notice that there are no Woody Allen pictures here. That is not a glaring oversight. In this current climate, I can’t bring myself to include his classic romantic comedies here. Like most cinephiles, I have in the past been a great appreciator of his work, and his movies are a large part of why I fell in love with movies in the first place. But I have undeniably gone through a reckoning these last few months. While it is true that there is currently no legal charges brought against Allen regarding his possible sexual assault, there is enough surrounding the case and the larger themes of his work to suggest that history might not be kind to his oeuvre. At this current juncture, this is enough for me not to want to promote and celebrate his movies that I have admittedly loved in the past.

2 thoughts on “Best Romantic Comedies

  1. Another wonderful collection you’ve compiled here! Always appreciate the breadth an varirty of films in your lists. Your reviews are always so wonderfully written and insightful, offering us multiple perspectives. I’ll need to watch/re-watch a few of these this week!

    Liked by 1 person

  2. Pingback: Hall of Fame #2: The Apartment – Homebody Movies

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