I'll Have What She's Having

The first part of our definitive list of the all-time greatest American romantic comedies

Romance is the spice of life. But a look at recent films seems to indicate a waning interest in the stories of what happens when two people fall in love. With the notable exception of sleeper hit Anyone But You, with internet darlings Glen Powell and Sydney Sweeney, the romantic comedy has been drowned out by the noise of superhero mashups, IP cash-ins, and sequels to sequels to sequels. But here’s the thing: we still love watching two attractive, sparkling, appealing people be drawn together. The movies are, in essence, an opportunity to bask in the glow of stars, and no genre boils down that appeal to its essence more than the rom-com. The original formula — boy meet girl; boy loses girl; boy gets girl — has been complicated and revised countless times, not least by the fact that romantic comedies no longer need to be about boy meeting girl anymore, but the delight we take in watching two people fall in love has never diminished. We have put together 50 of our all-time favorite English-language rom-coms for you to fall in love with. Part I is here; the sequel will roll out next month.

City Lights (Charlie Chaplin, 1931)

Less a romantic comedy than a comedy and romance bolted to each other, Chaplin’s greatest film emerged four years after the release of The Jazz Singer, when the silent film was already considered a relic of the past. “Hold my beer,” Chaplin said, and went ahead and made the greatest of all silent films, a rolling tribute to the splendors of the one-reel shorts he had made his name with, just in time for them to go extinct forever. The Tramp befriends a blind flower seller, who believes him to be a wealthy industrialist, and he scrimps and saves to protect her from eviction and restore her vision. The final scene, when she belatedly realizes he is her secret benefactor, is, according to James Agee, “enough to shrivel the heart to see, and it is the greatest piece of acting and the highest moment in movies.” I agree. — S.A.

Trouble in Paradise (Ernst Lubitsch, 1932)

So there isn’t actually a precise definition of just what the “Lubitsch Touch” was, but if you want to understand the concept, try this early masterpiece by the German émigré director and watch the segment in which Herbert Marshall’s Gaston and Miriam Hopkins’ Lily one-up each other with the various intimate items they have pilfered from each other without the other’s knowledge, culminating in Marshall offering to return Lily’s garter to her. We tend to think of the progression of the movies — and maybe of romantic comedies in particular — as a straight-line progression toward ever-greater sexual frankness. Lubitsch, especially in the pre-Hays Code era, finds delightful ways to talk about sex without talking about sex. A single montage here of ticking clocks and unanswered doorbells is more erotic than 99% of the nudity in contemporary entertainment. — S.A.

The Thin Man (W.S. Van Dyke, 1934)

William Powell and Myrna Loy drink copiously, hang out with their dog, and occasionally solve mysteries. Most romantic comedies are about falling in love, ending on the happily-ever-after of a first kiss or wedding bells. The Thin Man is far more interested in the texture of married life, and the easy affection of two people who’ve already seen each other naked. This movie is a sorta detective story, based on the novel by Dashiell Hammett, but it is far more interested in Nick and Nora’s aimless banter than any of its clues. The fantasy only goes so far, though; this married couple having a complete blast are, of course, childless. — S.A.

Bringing Up Baby (Howard Hawks, 1938)

To watch this screwball classic is to marvel at the work of three masters — in the director’s chair, Howard Hawks, and in front of the camera, Katharine Hepburn and Cary Grant. The plot is ridiculous, the banter speedier than a Shohei Ohtani fastball. Hepburn dazzles as an eccentric heiress (the best kind) who falls for a painfully handsome paleontologist (Grant, duh) and enlists him to help her transport a leopard named Baby to her farm in Connecticut. Hijinks ensue as Hepburn hides Grant’s clothing in a desperate attempt to delay his wedding to another woman. Grant is forced to wear her fur-lined negligée for one scene, and when a stranger at the door requests an explanation, the actor ad-libs, "Because I just went gay all of a sudden!” — E.C.

Holiday (George Cukor, 1938)

Hepburn and Grant banter and make sparks in Cukor’s brainy gem uniting a self-made dreamer (Grant, fine as hell) and an heiress with a rebellious streak (Hepburn, electric, her cheekbones as sharp as her tongue). Obviously, they’re made for each other. The problem: He’s dating her sister! The dialogue, reflective of the class warfare that existed in society amid the Great Depression, feels fresh and contemporary, as though it were written today. Hepburn: “Do you realize that you are trying to marry into one of America’s 60 families?” Grant: “When I find myself in a position like this, I ask myself, what would General Motors do?” — E.C.

A note from Saul: I think sometimes younger fans assume that all older comedies are going to be too slow for their tastes. And the reality of screwball comedies like these — and really anything with Hepburn and/or Grant — is that the pace of the dialogue is so fast that we sometimes struggle to keep up with it!

Ninotchka (Ernst Lubitsch, 1939)

Greta Garbo’s Soviet functionary looks at a particularly absurd, extravagant, utterly unnecessary example of French millinery and laughs to herself. Ninotchka has declared herself immune to all of Paris’ many allures, but this hat wins her over at long last, and clarifies what this movie’s intentions are. Yes, there is a wonderful boy-girl romance here, with Melvyn Douglas’ quasi-gigolo offering up sweet nothings in Garbo’s ear. But the true romance is between this symbol of rock-hard political dedication and the absurd and delectable society to which she unexpectedly finds herself attracted. Ninotchka is a rolling debate about politics disguised as a romance, with Ninotchka — and the audience — continually reminded of the hidden depths of shallow pursuits. In a restaurant, Ninotchka haughtily informs the proprietor that she never thinks about food, only “the future of the common people.” “That’s also a question of food,” he tells her. — S.A.

The Lady Eve (Preston Sturges, 1940)

“Positively the same dame!” Sturges’ astounding screwball comedy leans on a sleight of hand in which Barbara Stanwyck’s con woman, having already swept in for a quick payday by hoodwinking Henry Fonda’s rich and clueless snake enthusiast during a cruise, returns with a new name and new identity, and seeks to do it all over again, now as a British aristocrat named Eve. “If she didn’t look so exactly like the other girl,” says Fonda, “I might be suspicious.” Stanwyck is sexy and whip-smart and ruthless, and Fonda is superb as a well-heeled, kind-hearted buffoon, and the collision of these two disparate forces makes for Sturges’ most gleeful comedy. — S.A.

The Shop Around the Corner (Ernst Lubitsch, 1940)

You’ve Got Mail is all well and good, but if you want to see genuine romantic-comedy perfection, look no further than the original: Lubitsch’s elegant, aching trifle about wannabe-sweethearts who can’t stand each other’s faces in person and are drawn to each other’s souls via letter. The setting is a Budapest department store, and James Stewart and Margaret Sullavan are the star-crossed lovers, surrounded by Lubitsch’s familiar array of Ruritanian character actors, including the never-better Felix Bressart as Stewart’s hangdog pal. Shop is weighed down by the economic chaos soon to overtake the continent, and it is that very sense of deep personal and financial precarity that makes Mr. Kralik and Miss Novak’s romance all the sweeter. — S.A.

His Girl Friday (Howard Hawks, 1940)

The other Cary Grant classic, this one with Rosalind Russell as a hard-bitten newspaper reporter chasing the story of an escaped convict and Grant as her dazzlingly amoral editor — and ex-husband. Grant and Russell are, obviously, perfection — if you ever want to know what movie stars, a now seemingly-defunct species, were once like, watch this movie — but I also want to pause briefly to shout out Ralph Bellamy. Who, you might say? The handsome lunk who plays Hepburn’s fiancée, there to be outfoxed and outhustled by Grant, and ultimately lose in love. The comedies of the 1930s and 1940s were some of the greatest ever made because of the writers, directors, and stars who defined the medium, but also because of character actors like Felix Bressart, Thelma Ritter, Edward Everett Horton, and Bellamy, who could take the most unpromising of roles and give it precisely what the story needed. Thank you, Ralph. — S.A.

Adam’s Rib (George Cukor, 1949)

Like The Thin Man if its couple preferred argumentation to drinking, Adam’s Rib is another film about the happily-ever-after in which Katharine Hepburn and Spencer Tracy are married lawyers who find themselves on opposing sides in a case concerning a woman accused of the attempted murder of her husband. This proto-feminist comedy written by husband-and-wife team Ruth Gordon and Garson Kanin, in which Hepburn seeks to use this case to bolster the unsteady position of American women, is as much about what it might mean for a marriage to take on the patriarchy as anything else. Hepburn — spoiler alert! — wins the case, and immediately glances over at her husband, to see how he might be taking the loss. — S.A.

Singin’ in the Rain (Stanley Donen & Gene Kelly, 1952)

Yes, Singin’ in the Rain is unquestionably the greatest movie musical of all time. But it is also perhaps the most blissfully naïve and wistful of all romantic comedies, with Gene Kelly’s movie star won over by Debbie Reynolds’ ingenue. Kelly and Reynolds are delightful, of course, but much of the comedy comes via Donald O’Connor as Kelly’s sidekick, literally dancing up the side of a wall in his effort to “Make ‘Em Laugh,” and Jean Hagen as Kelly’s tone-deaf co-star. Little-known fact: in the storyline, Reynolds secretly serves as Hagen’s vocal double. In reality, Hagen sang all of Reynolds’ numbers. — S.A.

Desk Set (Walter Lang, 1957)

The married screenwriting duo Henry and Phoebe Ephron — the parents of Nora — were the brains behind what is possibly the most overlooked Katharine Hepburn-Spencer Tracy film ever. It is also one of the actors’ finest collaborations. Hepburn, always ahead of her time, plays mid-century working gal Bunny Watson, a reference librarian at a broadcast network in Manhattan. (Yes, an extremely specific job title!) Bunny is highly competent and deeply suspicious of Tracy’s character, an engineer and efficiency expert who’s invented a machine that her employer hopes will make the library function better. Will technology replace Bunny and render her jobless? In the age of AI, this fear remains as timely as ever. — E.C.

Funny Face (Stanley Donen, 1957)

If we want to get hyper-technical about it, we turn to romantic comedies because we want to bask in the presence of beautiful people. That beauty is very much about looks, don’t get me wrong, but is also a matter of the inner glow that certain performers let off. If there has ever been a performer who possessed more of both kinds of beauty than Audrey Hepburn, then I probably don’t want to know about it. And while Fred Astaire — “Can’t act. Slightly bald. Can dance a little,” goes the famous studio pronouncement from early in his career — is hardly Hepburn’s equal in the looks department, this paean to fashion photography is an adrenaline shot of pure joy, directed by Stanley Donen with the same fizz as his earlier Singin’ in the Rain. — S.A.

Pillow Talk/Down With Love (Michael Gordon, 1959; Peyton Reed, 2003)

Conventional wisdom has the Doris Day-Rock Hudson comedies of the 1950s and early 1960s as accidentally hilarious, absurdly prim and anti-erotic. Conventional wisdom is wrong, and Pillow Talk, which is very much in on the joke, is the greatest of their joint efforts. Directed by Michael Gordon, Pillow Talk brings together Hudson’s toxic bachelor and Day’s interior decorator, driven mad by his relentless wooing of an endless stream of women with the same tired ditty on their party telephone line. Day’s reputation as virginal and aloof is entirely belied by this suave romance, in which Hudson adopts the gentlemanly persona he thinks she would prefer as a mode of revenge, and she urges him on to make a move.

With its split screens and midcentury modern aesthetic, Pillow Talk was ripe for revisiting, with Peyton Reed’s homage/deconstruction Down With Love smoothly adopting its predecessor’s tone and style while also fitting in some sly winks at Pillow Talk’s sexual politics. Ewan McGregor is charming in the Hudson role, but Renee Zellweger is simply perfect as the 21^st-century version Doris. Why didn’t they make ten more of these? — S.A.

Some Like It Hot (Billy Wilder, 1959)

We often think about Marilyn Monroe as sui generis — the Platonic ideal of a movie star, lionized for her beauty and her too-short life — but that rose-colored glow loses sight of Monroe’s actual gifts. She was funny, and never more so than in Wilder’s story of male musicians (Tony Curtis and Jack Lemmon) posing as women while on the run from mobsters. Monroe’s Sugar Kane is into saxophonists and men with glasses, and she plays her own sex appeal for laughs, making this a movie less about a bombshell than about that rarest of things in 1950s Hollywood — a funny woman. Wilder did not enjoy the experience of directing Monroe one bit — “There are more books on her than there are on World War II,” he later said, “and I think that there’s a great similarity”— but the rest of us get to enjoy the fruits of their collective labor. Nobody’s perfect, but this film comes pretty close. — S.A.

The Apartment (Billy Wilder, 1960)

“What Would Lubitsch Do?” read a sign in Billy Wilder’s office, there to remind him of his mentor’s influence. The Apartment is the closest Wilder ever came to answering the question. This surprisingly bittersweet portrait of the corporate ladder is a relentless critique of the pursuit of success, letting Jack Lemmon’s striver be tempted by his glimpse of that legendary Shangri-La — the executive washroom — before realizing he prefers straining pasta with a tennis racket as long as he gets to do it in the company of Shirley MacLaine’s Fran Kubelik. Shut up and deal, indeed. — S.A.

Charade (Stanley Donen, 1963)

This valentine to Alfred Hitchcock’s thrillers shines as a showcase for Cary Grant and Audrey Hepburn, two performers whose luster has never dimmed. We watch them coil and swivel around each other as Hepburn seeks to escape the men chasing her for a fortune she did not know she had, but are most intrigued by the romance that blossoms between them. “Do you know what’s wrong with you?” Hepburn wonders. “Nothing.” If you’ve ever wondered why people still put posters of Audrey on their dorm-room walls, watch this film and instantly understand. — S.A.

Avanti! (Billy Wilder, 1971)

A man and woman, each visiting Italy, and mourning the loss of their parents, come to realize that their father and mother had been visiting the same resort, and cheating on their respective spouses, for decades. Lemmon is back, this time as blustering industrialist Wendell Armbruster Jr., who is in an infernal rush to get his father’s body back home, and deliver a eulogy to his 216,000 employees. “Love,” he tells Juliet Mills’ Pamela Piggott, “is for filing clerks, not the head of a conglomerate.” But after being forcibly subjected to Italy’s many wiles, he falls for the land, as well as for Pamela. Avanti! is like a capitalist inversion of Lubitsch’s Ninotchka, with another humorless workaholic wooed by European sophistication. — S.A.

Annie Hall (Woody Allen, 1977)

What to do with Woody Allen? I’ll let Claire Dederer have her say, from her book Monsters: “Annie Hall is the greatest comic film of the twentieth century — better than Bringing Up Baby, better even than Caddyshack — because it acknowledges the irrepressible nihilism lurking at the center of all comedy. ... Look, I don’t get to go around feeling connected to humanity all the time. It’s a rare pleasure. And I was supposed to give it up just because Woody Allen behaved like a terrible person? It hardly seemed fair.” But Dederer goes on to describe how impossible it was for her to revisit Allen’s Manhattan, and truth be told, I haven’t watched Annie Hall — or any of Allen’s films — in quite a few years. Consider this a blank space in which we collectively agree to store the memory of a great film that may best be left in memory. — S.A.

Modern Romance (Albert Brooks, 1981)

Most romantic comedies leave us feeling hopeful, satisfied, or emotionally drained, watching what happens when human beings go out in search of love. But what if a romantic comedy instead was like an alien’s report on human narcissism and self-absorption? Albert Brooks’ sophomore feature as a writer/director/star features him as Robert, a film editor unable to make up his mind about whether to stay with his girlfriend Mary (Kathryn Harrold). The movie is ultimately not about the resolution —there is none — than about Robert’s utter self-absorption. “It’s over,” Mary tells him. “Marry me,” Robert responds. This is the kind of movie where Mary says yes. (They later get divorced, but the final crawl tells us they’re dating once more.) — S.A.

Coming to America (John Landis, 1988)

No list of this sort would be complete without including Eddie Murphy’s wonderfully wacky comic masterpiece. Murphy projects both sweetness and silliness as Akeem, the prince of the fictional country of Zamunda, who rejects an arranged marriage and moves to Queens to find a queen of his own. He yearns to meet an independent woman, someone who knows her own mind and loves him for him, and not his fantastic wealth. Akeem gets a job at McDowell’s, a McDonald’s knockoff, and is soon smitten with Lisa (Shari Headley), the kind, sane daughter of the restaurant’s goofy owner (a wickedly funny John Amos). Headley, who radiates understated charm, is an equal partner worth waiting for. — E.C.

Say Anything (Cameron Crowe, 1989)

God, I loved this movie as a teenager! If we ever want to understand why people — myself very much included — have such a fondness for John Cusack, it might help to start with this movie. Everyone remembers the scene where he holds up the boombox playing Peter Gabriel’s “In Your Eyes” outside Ione Skye’s bedroom window, but I actually prefer the moment at the end of the film, when Lloyd patiently holds Diane’s hand as they wait for the “Fasten Your Seatbelts” sign on the airplane to turn off, and life to begin. — S.A.

When Harry Met Sally (Rob Reiner, 1989)

This beloved, endlessly quotable rom-com launched the genre’s second golden age at the turn of the millennium. Written by Nora Ephron and directed by Rob Reiner, and featuring star-making performances from Meg Ryan and Billy Crystal, it posed a question that tantalized audiences back then: Can men and women be friends … without sex getting in the way? Of course they can! But Reiner sided with cynical Harry on the hot topic. He also helped his mother, Estelle, make cinematic history by including her in Katz’s Deli’s infamous “orgasm scene.” It was she who delivered the iconic line, “I’ll have what she’s having.” — E.C.

Saul: …And generations of tourists still come to Katz’s hoping they’re going to catch a glimpse of Meg Ryan. Billy Crystal gives hope to all shlubby Jewish men everywhere that they, too, can be romantic-comedy stars.

Groundhog Day (Harold Ramis, 1993)

As far as time-loop rom-coms go, Groundhog Day is unbeatable. The movie struck gold with its cast led by Bill Murray (fabulously deadpan) and its concept (mean-spirited weatherman must relive Groundhog Day over and over again, until he changes his misanthropic outlook on life). Eventually, his saintlike producer, Andie McDowell, sees him with new eyes as he learns how to play the piano, make ice sculptures and prevent various disasters around town — all things he’s picked up in the existential limbo he’s in. Only when he begins to see the beauty in himself can he see the beauty in others. — E.C.

Saul: This movie really kicked off the entire second phase of Bill Murray’s career, where he stopped being an incorrigible wiseass and became a sad-eyed incorrigible wiseass. Would there be a Rushmore without Groundhog Day?

Sleepless in Seattle (Nora Ephron, 1993)

Ephron took a big risk when she wrote and directed a love story that broke all the rules — for one, Meg Ryan and Tom Hanks do not officially meet until the movie’s grand finale atop the Empire State Building. Ephron’s gamble paid off, big-time, with Sleepless making $227 million worldwide and proving itself to be the sleeper hit of the summer box office. It still holds up. As widowed single dad Sam Baldwin, Hanks is in top form, bringing humor and sensitivity to a role that only he could play. Meanwhile, Ryan seems to glow from within. Did you know she can peel an apple in one long, curly strip? — E.C.

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Thanks for reading, friends. If you watch any of these gems, we hope that you enjoy them. Our list of the all-time best rom-coms, part deux, will hit your inbox in the New Year. In the meantime, did we miss anything on our roster? Please tell us your favorite rom-coms!