Illustration: Nick Wanserski
A.V. To ZAn alphabetical survey of pop culture  

Chemistry is perhaps the most elusive of all cinematic ingredients. Critics can point to craft in elements like directorial technique, set design, editing, and the rest; great acting can be taught, and recognized as such. But chemistry is out of everyone’s hands. Either people have it with one another or they don’t. Until you get two people together and watch the sparks fly, it’s a complete X factor. But to take that essential romantic ingredient and add comedy on top of it? It’s like trying to film someone performing a flawless tightrope walk while simultaneously walking a second tightrope yourself. Thus, The A.V. Club has compiled the following A-to-Z list of most essential romantic comedies, to highlight the brilliance and difficulty of this remarkable cinematic balancing act.

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It should be noted that the rules for what movies qualify as a rom-com are tough to articulate: At a certain point, Supreme Court Justice Potter Stewart’s rule about pornography comes into play: We can’t define “rom-com” precisely, but we know it when we see it. Hence, something like The Graduate fails the test, while Punch-Drunk Love’s fundamental humor and romance at its heart allow it to make the cut. Plus, there are certain lauded qualities of contemporary rom-coms (such as the “comfort food” consideration) that rank as less meritorious in the evaluation of great cinema. Still, the below films all demonstrate the requisite ingredients in spades—and anyone not seeing their own treasured rom-com nominees are encouraged to make the case for them in the comments. Fighting for the object of your affection? That’s amore.

A: The Apartment (1960)

“Shut up and deal.” Billy Wilder was perhaps the master of comedic last lines (see also: “Nobody’s perfect”), but Shirley MacLaine’s response to “Miss Kupelik, I absolutely adore you” belongs to the rom-com annals. In this fairly bleak 1960 workplace comedy (possibly the only film on this list with a suicide attempt), Wilder hero C.C. Baxter (Jack Lemmon) fights for the love of an elevator operator while battling her clueless married boyfriend (Fred MacMurray), who also happens to be his boss. As much a statement on the pointlessness of the rat race as on the saving grace of love, The Apartment itself transforms from a clandestine hookup pad to a cozy nest where tennis rackets are used as spaghetti colanders, lit candles signify the highest level of fine dining, and a game of gin rummy is the surest sign of romance. [Gwen Ihnat]

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Runner-up: Annie Hall (1977)

Few films on this list have had as massive an impact on the modern romantic comedy as Annie Hall. Woody Allen’s mid-’70s masterpiece set the template for contemporary rom-coms with a staggering degree of new twists on old formulas. From the fourth-wall-breaking tactics of Allen’s nebbish protagonist to the master class in editing, the movie serves as the crowning jewel on his decade as America’s foremost cinematic humorist, and captures essential truths about urban romance at the same time. [Alex McCown]

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B: Bringing Up Baby (1938)

A love story about a paleontologist, a kook, a dog, a leopard, and a dinosaur bone, Bringing Up Baby is packed with so many gags that stars Cary Grant and Katharine Hepburn reportedly had trouble getting through takes without laughing, putting the movie behind schedule and over budget. Possessed by an overwhelming sense of comic energy, Howard Hawks’ screwball masterpiece heaps on misunderstandings, misadventures, perfectly timed jokes, and patter to the point that it’s easy to overlook how rich and fluid it is a piece of filmmaking, effortlessly transitioning from one thing into the next. The movie’s stick-in-the-mud/free spirit pair-up would go on to be imitated countless times, but never in a way that managed to capture the original’s sense of movement or its unique balance of pessimism and optimism. [Ignatiy Vishnevetsky]

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C: City Lights (1931)

Depending on how you look at it, City Lights was either Charlie Chaplin’s first sound film or his last silent movie; it has a soundtrack, but all of the dialogue is presented in inter-titles. Regardless of which era you put it in, this deeply eccentric film stands as the purest and most sublime of Chaplin’s masterpieces. Set in a fairy-tale city that resembles Paris and New York in equal measure, City Lights finds the Tramp—Chaplin’s iconic, mustachioed “gentleman vagrant” screen persona—falling in love with a blind flower seller (Virginia Cherrill) who mistakes him for a millionaire; afraid to disappoint her, he keeps up the ruse while trying to raise money for an eye operation. Chaplin spent two painstaking years shooting the film, refining and distilling every moment. (The first meeting between the Tramp and the Flower Girl, for instance, took months of work; the result moves with seemingly effortless grace.) Funny, bittersweet, and sensitive on levels that few movies can ever hope to reach, City Lights is one of the definitive romances of the big screen, building from episodic slapstick into one of the most moving endings in film. [Ignatiy Vishnevetsky]

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Runner-up: The Cutting Edge (1992)

D.B. Sweeney and Moira Kelly star as two world-class athletes whose Olympic dreams are deferred by an eye injury and stubbornness, respectively. Hockey player Doug (Sweeney) must alter course on his way to the gold, trading in his helmet for sparkly shirts to become Kate’s (Kelly) figure-skating partner. She’s imperious, he’s affable, so there’s no way they can work together, right? Of course, the pertinent rule of attraction dictates that these opposites will fall in love despite their differences. It’s a stale premise made fresh by Sweeney’s hangdog charm and Kelly’s vulnerability. [Danette Chavez]

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D: Don’t Go Breaking My Heart (2011)

With Don’t Go Breaking My Heart, Hong Kong-based Johnnie To and Wai Ka-Fai took on a white-collar love triangle with the same panache the duo had brought to their renowned hard-boiled crime films. Financial analyst Yen (Yuanyuan Gao), newly arrived from mainland China, spends her days flirting with playboy investment banker Sean (Louis Koo) whose office faces hers, and her nights bonding with alcoholic failed architect Kevin (Daniel Wu). Years later, as Hong Kong’s business sector begins to recover from the 2008 financial crisis, both men abruptly re-enter her life—except that now it’s Kevin, newly sober, who’s working in Sean’s old office space. Though best known in America for their macho genre movies, To and Wai have collaborated on countless romances and rom-coms with screwball lead extraordinaire Sammi Cheng; however, none of them ooze this much pure style. Scored to a lounge-and-exotica make-out soundtrack by Xavier Jamaux and packed with too many breathtaking visual compositions to count (plus left-field quotations from the likes of Playtime and Vertigo), Don’t Go Breaking My Heart turns a formulaic premise into one of the most endearing, graceful, and just plain beautiful rom-coms of the modern era. [Ignatiy Vishnevetsky]

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E: Enchanted (2007)

Disney went the live-action route for this princess story, which features Amy Adams as Giselle, a peasant girl with the requisite set of golden pipes, whose true love is thwarted by the requisite evil queen. Giselle’s exiled to New York City, where she needs immediate rescuing (from a billboard). Her reluctant champion comes in the form of Robert (Patrick Dempsey), a slightly jaded single dad and divorce attorney. Giselle’s unrelenting optimism erodes his cynical facade and they fall for each other, despite having already found more superficially suitable partners. The two leads have plenty of chemistry, but Adams’ performance is the real draw here. The actress brings her cartoon princess to multidimensional life, whether she’s experiencing doubt and anger for the first time, or switching roles to become the hero. The happy ending’s a foregone conclusion—this is Disney, after all—but Bill Kelly’s script pokes plenty of fun at the usual tropes, like rodent housekeepers and ill-advised dressmaking, along the way. [Danette Chavez]

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F: Four Weddings And A Funeral (1994)

A charming film that introduced the squidgy charms of Hugh Grant to the masses, Four Weddings And A Funeral was a surprise success when it arrived in theaters in the spring of 1994. It holds up even now, with Grant and Andie MacDowell anchoring a picture that’s full of both love and tears, as well as a surprisingly progressive (for the time) look at a same-sex relationship. Though the film’s certainly built around the will-they-or-won’t-they relationship between Grant’s Charles and MacDowell’s witty American, Carrie, John Hannah’s recitation of W.H. Auden’s “Funeral Blues” can prompt chills even now. [Marah Eakin]

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Runner-up: Forgetting Sarah Marshall (2008)

Jason Segel’s first screenwriting credit, Forgetting Sarah Marshall walks well-tread territory: Girl breaks up with boy, boy meets new girl, complications ensue. But the value of this rom-com is found in the spaces between the broad strokes. A cast of Judd Apatow supporting players adds oddball antics, pitch-perfect spoofs of CSI and celebrity gossip functions for laughs and narrative, and strangely poignant songs from Segel’s puppet rock opera starring Dracula make the film a stand-out. Forgetting Sarah Marshall doesn’t revolutionize the genre, but it does revitalize it. [Caitlin PenzeyMoog]

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G: Gentlemen Prefer Blondes (1953)

Any addict of the genre knows that the frothier the film, the tougher it is to pull off; something about the delicate nature of such wispy material can easily send lesser films flailing into the Earth. But 1953’s Gentlemen Prefer Blondes rises merrily into the clouds, a lighter-than-air concoction of whimsy and screwball absurdism. Marilyn Monroe and Jane Russell give note-perfect performances as Lorelai Lee and Dorothy Shaw, showgirls and best friends whose trip to France threatens to upend their lives completely. Monroe’s naïve gold-digger (and killer performance of “Diamonds Are A Girl’s Best Friend”) is what sticks with most people, but Howard Hawk’s masterful orchestration of all the narrative wheels—especially Russell’s exasperated efforts to protect her BFF from disaster—is what keeps the film timeless. Gentlemen may prefer blondes, but everyone should prefer this film to just about any competing sweet cinematic confections. [Alex McCown]

Runner-up: The Goodbye Girl (1977)

Richard Dreyfuss won an Oscar for playing the unlikeliest of romantic heroes: an unemployed actor. In this Neil Simon-penned script, his Elliot moves in with Marsha Mason’s Paula, The Goodbye Girl of the title, who has been ditched by yet another boyfriend who gave Elliot a lease on his way out. Of course, the close quarters lead to love, but the charm of the story is sold almost completely by Dreyfuss’ exuberance, whether he’s playing a horrific distortion of Richard The III, setting up a Casablanca-worthy dinner date on the roof, or winning over Paula’s daughter (Quinn Cummings) with a horse-drawn carriage. Who could resist? [Gwen Ihnat]

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H: Harold And Maude (1971)

This cult classic has shocked and charmed audiences since the early ’70s with its focus on the unorthodox love of Harold (Bud Cort) and Maude (Ruth Gordon), who were cast as approximately 19 and 79 years old, respectively. With a darker humor than most movies on this list, the age difference between Harold and Maude is contrasted in an abstract way. Instead of lingering on the societal aspect of the May-December romance, the film juxtaposes Maude’s strong sense of self with Harold’s feelings of insignificance—which often manifest themselves in hilariously gruesome gags. Throughout, Maude brings a brighter levity to the world around the couple and by the end of the film, she renders Harold’s comment, “I haven’t lived… I’ve died a few times,” moot after providing him with a wealth of unforgettable experiences and the sort of wisdom that only comes with age. As a bonus, the entire soundtrack is composed of Cat Stevens songs, his winsome folk lending itself well to what proves to be a rather pure and innocent love affair. [Becca James]

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Runner-up: High Fidelity (2001)

Purists may grumble about Nick Hornby’s tale of British record-store obsessives being shipped across the pond, but much like the protagonists from this tale of putting away childish attitudes, they need to learn to adapt. Stephen Frears nails the cynical, acerbic tone of modern-day music nerds who know everything about rock and almost nothing about life. John Cusack was born to play this role—it’s almost like Lloyd Dobler grew up and became disillusioned. Plus, to quote Barry, Jack Black’s spaz of a star-making role: The soundtrack kicks fucking ass. [Alex McCown]

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I: It Happened One Night (1934)

City Lights is older, but if there’s a safe choice for the granddaddy of all romantic comedies, this is probably it. One of only three films to ever sweep the major five Oscar categories, Frank Capra’s witty classic didn’t just legitimize the genre, ushering in a golden age of fizzy, star-powered battles of the sexes. It also basically wrote the blueprint for the modern rom-com. With the bickering, cross-country exploits of a pampered, engaged socialite (Claudette Colbert) and the brash reporter (Clark Gable) along for the ride that could be his big scoop, Capra pioneered the salty-then-sweet structure—that steady, reliable shift from antagonism to affection—that countless fans and imitators have adopted since. But It Happened One Night is more than an ancient artifact: In the sparkling rapport shared between its stars, the film remains as charming and funny as it must have looked back in 1934. It’s a merry-go-round you never want to get off. Hollywood hasn’t yet. [A.A. Dowd]

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J: Just Friends (2005)

Like Ryan Reynolds’ awkward-teenager-turned-beefy-careerist, 2005’s Just Friends has gotten better with age, even if that fat suit looked dated before the movie hit theaters. Just Friends thrives within the limits of the genre, gleefully rehashing its touchstones: The romantic rival, the obnoxious family members, the grand gestures that take things just a little too far. There’s a quaint charm to this homecoming rom-com, even when it plays its laughs as big and broad as possible. Reynolds, for his part, sells the hell out of the slapstick, only out-performed by Anna Faris, who walks away with the movie thanks to her sublimely silly and self-interested turn as a modern pop starlet. But balancing out the cartoonish antics is the relatable story of an unrequited love, one lent heaps of sweetness by Amy Smart’s song-worthy girl next door, Jamie Palomino. It may not be the genre at its most refined, but it feels goofy and light-hearted, just like a high school crush. [Cameron Scheetz]

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K: Knocked Up (2007)

Were this a rundown of the best bromantic comedies every made, writer-director Judd Apatow would have the alphabet on lockdown. Still, for all the platonic love stories he and his stable of Freaks Ands Geeks alums have told over the last decade, Apatow can still do boy meets girl better than most of his contemporaries. Knocked Up is his funniest, sweetest contribution to the genre, an opposites-attract charmer about a slacker doofus (Seth Rogen) and a budding entertainment reporter (Katherine Heigl) who try to make things work after their one-night-stand leads to an unwanted pregnancy. While Apatow helped pioneer the process of applying rom-com conventions to (in Neighbors’ parlance) bros-before-hos camaraderie, Knocked Up does something close to the opposite: It’s the date movie by way of mismatched buddy comedy. And while Heigl later decried (and not totally unfairly) the implied sexism of Apatow’s boys-club humor, none of her subsequent rom-com vehicles possessed a part as good as exasperated, headstrong Alison Scott—or for that matter, jokes half as funny as the ones she and Rogen get to fire off scene by scene here. Few romantic comedies nail the comedy half of their equation better. [A.A. Dowd]

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L: The Lady Eve (1941)

Henry Fonda’s “Hopsie,” a clueless heir/snake specialist who’s been up the Amazon for a year, doesn’t have a chance against Barbara Stanwyck’s Jean, a con artist on the make with bewitching perfume and legs to die for. When the two collide on an ocean liner, to no one’s surprise, Jean falls for him for real, while dazzling him with Preston Sturges’ dialogue, which he wrote expressly for Stanwyck. After a misunderstanding tears them apart, Jean wails, “I need him like the ax needs the turkey,” so she pulls off an even bigger con to get him back. Men are hopelessly outclassed in Sturges’ witty battle-of-the-sexes comedy (snakes, Eve, you get it), which was considered quite risqué in 1941 and still sizzles decades later. By the end of the movie, you’ll be as confused as Hopsie, and just as besotted. [Gwen Ihnat]

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M: My Best Friend’s Wedding (1997)

It’s not often we get to see a rom-com star of Julia Roberts’ stature miss out on her expected happy ending. But it is this realism that makes My Best Friend’s Wedding a must-watch. Childhood friends Julianne Potter (Roberts) and Michael O’Neal (Dermot Mulroney) had a deal to marry each other if they were still single by age 28 (that they didn’t even attempt to push it to 30 is the true comedy), and just four days before Julianne’s 28th birthday, Michael does the unthinkable by announcing he has fallen in love with and intends to marry a woman (Cameron Diaz) that is very well-suited to him. Julianne, of course, does what lot of leading ladies in rom-coms do, which is act a complete fool with no regard for the feelings of those around her. Normally, this is somehow written off as endearing and the “other woman” is kicked to the curb never to be heard from again. Not this time. Watch it for the often much-needed reminder that real love is selfless and marriage before 30 isn’t mandatory. [Becca James]

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Runner-up: Moonstruck (1987)

Somehow a 1930s screwball comedy landed right in the middle of the ’80s, giving us the phrase, “Oscar-winner Cher.” Framed around an opera, Moonstruck told the story of Loretta (Cher), a mousey bookkeeper who falls for her fiancee’s brother, thus introducing the world to the post-Valley Girl romantic masteries of Nicolas Cage. The romance is justifiably great (let us never forget: “Snap out of it!”), but it’s Moonstruck’s ageless moments of New York Italian family life that resonate—like frying eggs in bread, going to confession, and keeping several generations of the family always together. Olympia Dukakis also won an Oscar playing the no-nonsense matriarch, who realizes she can’t control a daughter ruled by a romance-inspiring moon. [Gwen Ihnat]

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N: Never Been Kissed (1999)

Drew Barrymore has made countless romantic comedies over the course of her 30-odd year tenure in Hollywood, but none are as winning as Never Been Kissed, the 1999 film that found her playing adult reporter turned undercover teen Josie “Grossie” Gellar. Though much of the film’s humor comes from Josie’s attempts to fit in at her suburban Chicago school in an attempt to get a story for the Chicago Sun-Times, Never Been Kissed is still, at its heart, a love story between Josie and Michael Vartan’s Sam. As Josie’s English teacher who’s afraid to acknowledge his burgeoning feelings for his student, Vartan is handsome and charming, even when he almost leaves Barrymore hanging at the film’s heart-stopping conclusion. [Marah Eakin]

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O: Overboard (1987)

Given the more than three decades long real-life romance of actors Kurt Russell and Goldie Hawn, any movie they’re in together is especially heartwarming, even if it’s otherwise problematic: Rich snob Joanna Stayton (Goldie Hawn) suffers amnesia after falling overboard her yacht, and her husband Grant (the late Edward Herrmann) sees this as his opportunity to escape the lackluster marriage. Meanwhile Dean Profit (Kurt Russell) decides to claim Joanna as his wife by lying to her about her entire life and their love. Although Joanna cannot remember her past, she has trouble believing she was ever meant to be a working-class mother of four and eventually she snaps back to reality. By that time, however, she has fallen in love with her new family, one which opened her heart up in a way Grant was never willing or able to do. Is it Stockholm syndrome? Given how much better a person Joanna is by the end of the film, it’s hard to say. [Becca James]

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P: Punch-Drunk Love (2002)

Though its pedigree causes some to forget what genre it belongs to, Punch-Drunk Love stands out in the rom-com world. It’s writer-director Paul Thomas Anderson’s most compact feature film, and easily the best case that can be made for Adam Sandler as a “real” actor. Sandler plays Barry Egan, who falls for Emily Watson’s Lena Leonard, and their budding romance causes Barry to take charge of his life as he transforms from a temperamental, ineffective fellow into someone with a modicum of self-confidence. Both the film and its humor are incredibly dark, but that’s what makes Punch-Drunk Love’s softer moments feel truly sweet. In an incredibly crowded “P” category, Punch-Drunk Love stands above the rest not for its ability to be playfully romantic, but its dedication to being painfully human. [David Anthony]

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Runner-up: Pretty In Pink (1986)

There’s a Cinderella story, a love triangle (some might say square), and a class struggle all wrapped up in this John Hughes romantic comedy which, fittingly enough, culminates in an all-important dance. High-school senior Andie (Molly Ringwald) dares to make her way over from the wrong side of the tracks to be with Blane (Andrew McCarthy), a bland preppy kid. Her friend Duckie (Jon Cryer) isn’t exactly supportive, carrying a torch for her as he does. Blane buckles under peer pressure and ditches Andie before the senior prom, so she stitches some pink armor to show the snobs that they didn’t break her. Her bravery wins Blane’s heart again, and to this day we still hope he eventually did something to deserve it. [Danette Chavez]

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R: Roman Holiday (1953)

Rarely do stars emerge as fully formed in their big-screen debuts as Audrey Hepburn in Roman Holiday. Everything about the actor, from her radiant appeal to the winning charisma that practically hugs you from within the film, was already in place for her first star turn as Princess Ann, the young royal who slips her handlers and falls for American journalist Joe Bradley (Gregory Peck). Even Peck knew something special was happening—midway through the shoot, he suggested to director William Wyler that he share top billing with this unknown ingénue. And the two earn their co-billing, with Peck playing the irascible counterpoint to Hepburn’s wide-eyed determination. It’s a testament to the film’s staying power that, even now, it plays like a cast and crew just discovering how joyful making cinema could be. [Alex McCown]

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S: Say Anything (1989)

Is there a more iconic image in modern romantic cinema than John Cusack standing outside the window of his high-school crush, boom box lifted over his head, Peter Gabriel articulating every sweet nothing he can’t? Cameron Crowe could make a hundred more movies as stilted as Elizabethtown or Aloha and his fans would keep showing up, like Lloyd Dobler at that window, hoping for half the tingles they got from his cherished directorial debut. Say Anything… is best remembered for that grand romantic gesture, but its timeless appeal lies more in the small scale of its adolescent love story: Anyone who’s fumbled, awkwardly but sincerely, from infatuation into a fledgling relationship should see a little of themselves in Cusack’s big-hearted, underachieving Lloyd, or in brainy beauty Diane (Ione Skye), the shy valedictorian he courts. Crowe would sporadically recapture some of the magic of his seminal teen movie, but to paraphrase another of his most popular romantic comedies, he had us at Say Anything… [A.A. Dowd]

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Runner-up: Sleeping With Other People (2015)

A recent staple of rom-coms has been the couple who sets clear “just friends” boundaries, only to find themselves unable to keep their mitts off one another. In Sleeping With Other People, writer-director Leslye Headland marches into this trope head-on, confidently and hilariously giving it new life, thanks to a sharp script and the smart-ass chemistry of her leads (Alison Brie and Jason Sudeikis). It may only be a few months old, but Sleeping With Other People’s masterful take on the genre makes the case for its inclusion among the rom-com classics. [Cameron Scheetz]

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T: Trouble In Paradise (1932)

What good is a list of rom-coms without an appearance by the first master of the genre? Ernst Lubtisch initially shot to fame his native Germany during the silent era, but relocated to Hollywood right as talkies were coming around. Sophisticated, witty, and unexpectedly moving, Lubtisch’s American romantic comedies defined what it meant for a movie to have style. And though The Shop Around The Corner and Ninotchka make strong contenders for Lubitsch’s best work in the genre, we’ll go with the sparkling, Art Deco Trouble In Paradise, perhaps the most Lubitsch-esque of all Lubitsch movies. One of the best-known examples of the Pre-Code era—that brief window in the early 1930s when Hollywood was rife with innuendo, sex, and flagrant amorality—Trouble In Paradise centers on a professional thieves Gaston (Herbert Marshall) and Lily (Miriam Hopkins), whose latest heist snags a hitch when Gaston starts falling for the mark (Kay Francis). Set in a Europe of the romantic imagination and packed with a seemingly endless supply of bon mots, Trouble In Paradise is everything a movie should be, and more. [Ignatiy Vishnevetsky]

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U: Under The Tuscan Sun (2003)

A “mature” romantic comedy (in that it stars Diane Lane as a scorned ex-wife who’s decamped to Tuscany in an attempt to get her groove back), Under The Tuscan Sun isn’t necessarily laugh-out-loud funny. Instead, it’s sunny and pleasant, with Lane’s Frances Mayes falling in love more with life itself over the course of the film than with the American writer she ultimately has sparks with toward the movie’s conclusion. With a cast including Sandra Oh, David Sutcliffe, and Kate Walsh, the film is a good—if occasionally heavy-handed—reminder that love can happen anywhere and anytime, even to those who’ve been wronged in the past. [Marah Eakin]

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V: Valley Girl (1983)

Squeals for star-crossed lovers! In this ’80s-soaked love story, teenagers Julie Richman (Deborah Foreman) and Randy (Nicolas Cage, in a very early film role that requires a lot of eyeliner) must throw caution to the wind and believe a prep and a punk can make it in this crazy world. Despite repeated protests from their respective friends, the two engage in a romance for the ages, which leads to a memorable montage as Julie and Randy sip a shared cola, walk by a lot of neon signs, and make out—all to Modern English’s “I Melt With You.” It’s hard to argue with the lyrics “the future’s open wide,” when, indeed, Julie and Randy have their whole lives ahead of them. Oh, to be young forever. [Becca James]

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W: When Harry Met Sally (1989)

More than any other movie on this list, When Harry Met Sally feels like the romantic comedy. That’s not to say it’s the best or most influential of its kind, though you could certainly make the case for both. Rather, Rob Reiner’s box-office hit just seems to perfectly embody what people want and expect from the genre: the sparks of chemistry between two young, expertly matched stars; the quick-witted banter, delivered during one dialogue-heavy scene after another; the transformation of New York, all bustle and bright lights, into the best place, the only place, for two fast friends to realize they might be something more. When Harry Met Sally made the careers of Meg Ryan, Billy Crystal, and screenwriter Nora Ephron; its impact can be felt in just about every rom-com released in its wake, not to mention something as deceptively antithetical as Seinfeld. The New York Times called it sitcom Woody Allen, which was meant as an insult, but comes close to capturing its enduring appeal: the neurotic, quotidian wit of something like Annie Hall, but carefully sanded into an irresistible crowd-pleaser. [A.A. Dowd]

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Runner-up: While You Were Sleeping (1995)

The story of a transit worker who sniffs an unconscious man’s coat and deceptively convinces his family that she’s his fiancée could quickly swing into creepy stalker territory if not for the charm of its lead. Sandra Bullock leapt from Speed into her first starring role here, cementing her space in the rom-com firmament. Bullock’s good-hearted but lonely orphan Lucy ostensibly has good reasons for claiming she’s her comatose crush’s fiancée (something about Grandma’s heart condition), which leads her to fall for the entire family, especially coma boy’s brother. Bullock’s pull is so strong she even turned perennial guy-who-never-gets-the-girl Bill Pullman into a swoonworthy lead. [Gwen Ihnat]

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X: Xanadu (1980)

In all honesty, Xanadu didn’t have a lot of competition, meaning it was able to roller-skate its way to the top of the “X” heap without any legitimate challenges. A lucky break for Xanadu, really, because the film is a mess—a gloriously entertaining one, but a disaster nonetheless. The plot, so far as it can be discerned, involves artist Sonny Malone (Michael Beck) becoming obsessed with a mysterious woman named Kira (Olivia Newton-John) who collides with him on the street and skates off, but not before having proffered a short kiss. What Sonny doesn’t yet know is that Kira is actually Terpsichore, the Olympian Muse of dance, who came to Earth via the portal of a mural. It only gets stranger from there, as Sonny opens a nightclub, “Kira” falls in love with him, there’s an argument with Zeus… and that’s not even mentioning Gene Kelly (yes, the Gene Kelly) as a former big-band leader turned construction mogul. It’s not the best romantic comedy on the list, but it’s almost certainly the weirdest. [Alex McCown]

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Y: You Can’t Take It With You (1938)

Based on a Pulitzer-prize winning play, Frank Capra’s You Can’t Take It With You has an important message that still stands eight decades later: Don’t sell out. At the center of this madcap comedy—an eccentric and creative family battles some no-good money-grubbing developers—is the romance of the impossibly young Jimmy Stewart (heir to the money-grubbers) and raspy-voiced Jean Arthur (offspring of the eccentrics). This Romeo and Juliet pairing brings all the families and issues together, making for a lovely and lively romantic backdrop against creative and individualistic principles. As Jimmy sputters to Jean, “Sometimes you’re so beautiful it just gags me.” [Gwen Ihnat]

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Z: Zelig (1983)

Deception has been a staple of romantic comedies since the beginning, so it makes sense that Woody Allen’s mockumentary about an enigmatic man who compulsively imitates everyone around him eventually turns into a love story. Seemingly riffing on his reputation for playing the same character in every movie, Allen stars as human chameleon Leonard Zelig, a forgotten minor celebrity of the 1920s and ’30s, while Mia Farrow plays Dr. Fletcher, the psychiatrist who ends up falling in love with him—an inversion of the usual dynamic between deceiver and deceived. Using black-and-white footage, doctored photos, and interviews with high-brow talking heads and real-life celebrities from the Jazz Age, Allen creates a clever alternate history that is, in a way, its own act of deception—namely, a cover-up for the fact that this is one of his most personal and self-critical projects, allegorically addressing his sense of Jewish identity, his high-brow aspirations post-Annie Hall, and his attempts at imitating his favorite directors. Sure, the love story is arguably the least interesting thing about Zelig, but this is still a fascinating work by a writer-director whose rom-coms all but beg to be read personally. [Ignatiy Vishnevetsky]

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