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50 Greatest Romantic Comedies of All Time

From ’30s screwballs to 21st-century meet-cutes, Rock and Doris to Hanks and Ryan — our picks for the best rom-coms ever

Say Anything, Moonstruck, When Harry Met Sally

Moviestore Collection/Shutterstock (2);Castle Rock/Nelson/Columbia/Kobal/Shutterstock

Take two people. Find a way to pair them up — maybe they’re on a cross-country trip together, maybe they both work in the same office, maybe they’re rivals in the same industry. Better yet, they might even be two parts of a love triangle. The scenarios are endless. Now throw some obstacles in their way, from geography to class issues to vengeful exs and/or brand new beaus. Or the conflict could be as easy as the fact that they just don’t like each other — in fact, they despise the other person. Then, after a lot of comic shenanigans and trying circumstances, they realize that they’re really meant for each other. Cupid’s arrows hit their marks. Roll credits.

It sounds simple, right? But to make a great romantic comedy — like, a really classic, stand-the-test-of-time one — requires skill, chops, expert timing, the right chemistry among your leads and the ability to pull heartstrings and hit funny bones at the same time. It’s a tougher balancing act than most folks would care to admit, and all the more impressive when filmmakers and actors actually do pull it off.

And the romantic comedies we’ve singled out here aren’t just impressive — they are, in our humble opinions, the cream of the genre crop, the best of the best. In honor of Valentine’s Day, a.k.a. the holiday where everyone craves both rom-com viewing time and argument-starting ranked lists, we present our choices for the 50 best rom-coms of all time. From ’30s screwballs to 21st century meet-cutes, Rock and Doris to Tom and Meg, these are the ones that had us at “hello.”

CONSTANCE WU-Rachel Chu; HENRY GOLDING-Nick Young;
50

‘Crazy Rich Asians’ (2018)

Jon M. Chu’s adaptation of Kevin Kwan’s novel scored a major representation coup and resurrected the summer rom-com in a funny, fluffy fantasy filled with palpable chemistry between leads Constance Wu and Henry Golding. As Nick, newcomer Golding is the dashing eye candy, while Wu gives a spectacular performance as the fiery striver Rachel, who struggles to balance her love for her privileged Singaporean boyfriend with her identity as a first-generation daughter of a Chinese single mother. The story culminates in a lavishly dreamy wedding, with the spine-tingling glances Wu and Golding share in that scene a potent reminder of just how powerful the rom-com can be. KW

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Editorial use only. No book cover usage.Mandatory Credit: Photo by Bob Marshak/Columbia/Tri-Star/Kobal/REX/Shutterstock (5883523d)Diane Keaton, Jack NicholsonSomething's Gotta Give - 2003Director: Nancy MeyersColumbia/Tri-StarUSAScene StillComedyTout peut arriver
49

‘Something’s Gotta Give’ (2003)

Come for writer-director Nancy Meyers’ drool-worthy interiors; stay for Jack Nicholson and Diane Keaton’s pas de deux, which turns on the idea that — gasp! — it’s possible for an older man to fall in love with a woman his own age. Keaton is esteemed playwright Erica Barry, whose cool confidence is ruffled when Nicholson’s Harry Sanborn, a perma-bachelor who’s dating her thirtysomething daughter, suffers a heart attack at her (absurdly elegant) Hamptons beach home. Guess where he ends up recuperating? The joy of this film is in watching Jack and Diane deftly nail their repartee like the old — and we mean that in the best possible way — pros they are. MF

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Adam Sandler The Wedding Singer - 1997
48

‘The Wedding Singer’ (1998)

Adam Sandler’s ’80s-music wedding singer and Drew Barrymore’s reception-hall waitress are engaged to other people — he to his crass, social-climbing high-school sweetheart Linda, she to douchey bond trader Glenn. As those relationships teeter, the two get closer, but they don’t reveal their true feelings until Sandler’s big number: an original song, “Wanna Grow Old With You,” performed to Julia on a flight to Las Vegas. (With an assist from first-class passenger Billy Idol — a nice day for a white wedding indeed.) It was the first of three collaborations for Sandler and Barrymore, who surprisingly made for a nice salty-and-sweet rom-com combination. MF

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Sandra Bullock, Ryan Reynolds in The Proposal - 2009Credit: Touchstone/Kobal/REX/Shutterstock
47

‘The Proposal’ (2009)

You can’t spell rom-com without Sandra Bullock, who found early success in the genre (Love Potion No. 9While You Were Sleeping) before a mid-career detour to focus on just-roms, just-coms and, er, drams. But paired with Ryan Reynolds in this surprise hit, she was back in top form. The star plays an icy, hard-charging publishing executive facing deportation to her native Canada; he’s her lowly (but hot) assistant, promised a promotion if he marries her for a Visa. The long-on-charm duo bring out one another’s talent for weapons-grade sarcasm and dry wit. Bonus points for comedic goddess Betty White, who waltzes through her every scene as Bullock’s kooky grandmother. MF

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Joseph Gordon-Levitt, Zooey Deschanel 500 Days Of Summer - 2009Credit: Watermark/Kobal/REX/Shutterstock
46

‘(500) Days of Summer’ (2009)

He (Joseph Gordon-Levitt) is a guy who writes greeting cards; she (Zooey Deschanel, in a dry run for her future adorkable phase) is the assistant to his boss. They meet in an elevator (is there a better opening line to a relationship than “I love the Smiths”?). Then they fall in love, fall out of love and break up. Only not in that order — and that’s where Marc Webb’s rom-com distinguishes itself from the pack. We get to observe their coupledom out of sequence, with a late, end-of-days argument here and an early, starry-eyed date there; the time limit is in the title, which casts a bittersweet glow over even the happiest scenes. That said, this will forever be known as The Movie In Which Joseph Gordon-Levitt Leads a Musical Number Set to “You Make My Dreams” — a pretty good legacy for any romantic comedy, really. DF

Crazy Stupid Love - 2011
45

‘Crazy, Stupid, Love’ (2011)

Consummate playboy Jacob (Ryan Gosling) meets his match in the form of shy but whip-smart Hannah (Emma Stone), who coaxes him through actual conversation into dropping his guard — and losing his shirt. The complexifier? Unbeknownst to the young couple, Jacob is also serving as dating coach to Hannah’s dad, Cal (Steve Carell), who’s navigating a trial separation from his cheating wife Emily (Julianne Moore). Amid the intersecting plots, it’s Jacob’s and Hannah’s love story that stands out — the movie successfully taps Stone’s gift for unselfconscious sexiness and Gosling’s gift for, well, being Gosling (his character is basically a superfit avatar of the actor’s “Hey Girl” persona). La La Land director Damien Chazelle clearly took note. MF

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Editorial use only. No book cover usage.Mandatory Credit: Photo by Apatow Productions/Kobal/REX/Shutterstock (5885051aj)Mila Kunis, Jason SegelForgetting Sarah Marshall - 2008Director: Nicholas StollerApatow ProductionsUSAScene StillComedySans Sarah rien ne va!
44

‘Forgetting Sarah Marshall’ (2008)

Jason Segel puts his everyman appeal to work as sad-sack Peter Bretter, a composer for a CSI-like TV show who breaks up with its narcissistic star Sarah Marshall (Kristen Bell). Cue a rebound relationship with down-to-earth Hawaii hotel clerk Rachel (Mila Kunis) at the same place his ex is staying. Producer Judd Apatow’s fingerprints are all over the goofy, bro-tastic humor, but, atypically, the female characters are fully realized humans: They enjoy sex without shame! They acknowledge their flaws and work to better themselves! Russell Brand rounds out the ensemble with a note-perfect take on Sarah’s new boyfriend, the pompous, faux-spiritual rock star Aldous Snow. With blow-job jokes and tender moments alike, it’s the rare rom-com with something for everyone! MF

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Reality Bites pictured:  Janeane Garofalo,  Winona Ryder,  Steve Zahn,  Ethan Hawke
43

‘Reality Bites’ (1994)

This Ben Stiller-directed time capsule puts two of the Nineties’ most appealing stars in a slacker-tinged cat-and-mouse game. Ethan Hawke ruined the love lives of Gen-X and Gen-Y women alike for at least a decade as Troy Dyer, a broody philosophy major whose intellectual pretensions are outpaced only by his allergic reactions to sentiment. Winona Ryder — possibly the original manic pixie dream girl — is the doe-eyed wannabe documentarian Lelaina Pierce. After a cigarette-smoke-filled montage of a mopey separation set to U2’s “All I Want Is You,” our bearded commitmentphobe arrives at Lelaina’s doorstep to make The Big Speech just as she’s leaving to go find him. Cue swoons, big kiss, credits. MF

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Editorial use only. No book cover usage.Mandatory Credit: Photo by Joseph Lederer/Columbia/Kobal/REX/Shutterstock (5881196n)Steve Martin, Daryl HannahRoxanne - 1987Director: Fred SchepisiColumbiaUSAScene StillRoxane
42

‘Roxanne’ (1987)

As writer and star, Steve Martin takes on the legend of Cyrano de Bergerac, playing C.D. Bales (C-de-B, get it?), a small-town fire chief with a really big nose — and an even bigger brain. He helps hunky dolt Chris (Rick Rossovich, Top Gun’s Slider) woo stunning astronomer Roxanne (Daryl Hannah) with coaching delivered via earpiece and, later, artfully crafted love letters. A performer whose comedy is always grounded in pathos, Martin (here wearing a fake schnoz that took an hour and a half to apply every day) brings a genuine sweetness to the role that keeps you rooting for the funny-looking good guy the whole way through. MF

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Taye Diggs, Nia Long in The Best Man - 1999
41

‘The Best Man’ (1999)

Taye Diggs is Harper, a Chicago writer who hits the jackpot when Oprah picks his debut novel for her book club. The only catch? He’s heading off to New York to see his old college friends at a wedding — and they’re passing around advance copies, buzzing about all the secrets he reveals. Like, say, his fling with the bride. Or the fact that he’s not over his ex Jordan (Nia Long). Writer-director Malcolm D. Lee (Spike’s cousin) assembled a dream team of up-and-coming actors, including future Empire star Terence Howard. It inspired a 2013 Christmas sequel (The Best Man Holiday), but the original remains a cult favorite — including the finest “Electric Slide” scene in the history of movie weddings. RS

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Go Fish,  V S Brodie,  Guinevere Turner
40

‘Go Fish’ (1994)

Director Rose Troche and co-writer/star Guinevere Turner set out to make a 16mm black-and-white indie movie that portrayed modern sapphic culture as something other than exotic or tragic — and in the process, they gave the world a first-rate lesbian rom-com. Max (Turner) is coming off a long dating sabbatical when she meets an older woman named Ely (V.S. Brodie). Sparks don’t fly at first; the latter also has a longtime, long-distance girlfriend as well. Eventually, thanks to some friends’ counseling and a well-timed “I Never …” party game, a genuine connection starts to form. A key work of the New Queer Cinema, this isn’t just a corrective to years of LGBTQ stereotypes — it’s fleet, funny and still feels like a breath of fresh air. DF

Renee Zellweger- Bridget Jones's Diary - 2001
39

‘Bridget Jones’ Diary’ (2001)

Leading up to the film’s release, it seemed that all anyone could talk about was Renée Zellweger’s gaining 30-odd pounds to play the “spinster” heroine of this modern spin on Pride and Prejudice. But her actual performance as the hapless yet indomitable British journalist — complemented by the smarmiest-ever Hugh Grant as her womanizing boss, Daniel Cleaver, and Colin First in classic, stiff-upper-lipped form as her “true love” Mark Darcy — earned Zellweger an Oscar nomination. Throw in a crackling ensemble cast who deliver signature Richard Curtis zingers with precision, and you have a romantic comedy so satisfying it spawned two sequels. MF

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Editorial use only. No book cover usage.Mandatory Credit: Photo by Touchstone/Kobal/REX/Shutterstock (5876507d)Heath Ledger, Julia Stiles10 Things I Hate About You - 1999Director: Gil JungerTouchstoneUSAScene StillShakespeareComedy
38

’10 Things I Hate About You’ (1999)

The Nineties couldn’t get enough Shakespearean remakes, from Romeo + Juliet to My Own Private Idaho — but this punk Taming of the Shrew set in a Seattle high school tops them all. It made stars out of newcomers Heath Ledger and Julia Stiles, with the latter playing a tough cookie who drives to school blasting Joan Jett and who’s into “Thai food, feminist prose and angry girl music of the indie-rock persuasion.” So naturally Heath sets out to woo her by name-dropping Bikini Kill and the Raincoats, which was unspeakably weird for a Hollywood movie. And even their geek pals manage to find romance at the prom via fetishistic Bard cosplay. RS

Editorial use only. No book cover usage.Mandatory Credit: Photo by Ugc/Studio Canal+/Kobal/REX/Shutterstock (5880341b)Audrey TautouAmelie - 2001Director: Jean-Pierre JeunetUgc / Studio Canal+FRANCEFilm PortraitLe Fabuleux Destin D'Amelie Poulain
37

‘Amelie’ (2001)

A huge crossover hit for French director Jean-Pierre Jeunet and the movie that inspired a thousand bob haircuts, this tale of a daydreaming waitress (Audrey Tatou, très adorable) who begins helping out her fellow neighborhood lonelyhearts and lost souls starts out as a cute ‘n’ comic Gallic fantasy. Then our heroine sees Nino (Mattheiu Kassovitz), a customer who collects random photos, and she turns into a puddle. (Like, literally turns into a puddle. It’s that kind of movie.) The scene in which they finally connect and she silently points to her lips so this shy man will kiss her is heart-melting; the final image of them tooling around Montmartre on a scooter, Amelie nuzzling her newfound true love, is like a 10cc injection of pure, uncut amour. DF

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Editorial use only. No book cover usage.Mandatory Credit: Photo by Sarah Shatz/Apatow/Kobal/REX/Shutterstock (8877347ba)Zoe Kazan, Kumail Nanjiani"The Big Sick" Film - 2017
36

‘The Big Sick’ (2017)

You’re supposed to write what you know, right? So comedian Kumail Nanjiani (Silicon Valley) and his real-life wife Emily V. Gordon penned up a script about how they met, fell in love — and then how she nearly died while he sat by her hospital bedside. Zoe Kazan plays Gordon’s screen counterpart; Nanjiani plays himself. And you play the audience member who finds yourself won over by this true tale of true love, and doubling over every time the writer-star drops one of his devastatingly dry punchlines. A classic boy-meets-girl, girl-falls-into-coma, boy-and-girl-write-Oscar-nominated-movie-about-it rom-com, in other words. DF

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Set It Up
35

‘Set It Up’ (2018)

This immensely charming Netflix original delivers a double dose of romance in a tale of two beleaguered assistants, Harper and Charlie, who set up their demanding bosses in order to get a little relief. Young stars Zoey Deutch and Glen Powell nail the rapid-fire screwball-style dialogue that makes the two pals such a perfect match. While Harper and Charlie are “parent-trapping” their higher-ups, a beautiful friendship based on mutual support and deep understanding blossoms. Their romance is more than well-earned. All that plus a roller-coaster tryst between two Type-A personalities played outlandishly by Taye Diggs and Lucy Liu. KW

Pretty Woman,  Richard Gere,  Julia Roberts
34

‘Pretty Woman’ (1990)

No, the rosy patina on sex work and the stink of white male privilege can’t be undone — but Julia Roberts’ breakthrough performance remains undeniably dazzling. Exuberant and vulnerable, the then-21-year-old actress dominates every scene, and it would be a big mistake (huge!) to dismiss her as a mere cog in an anti-feminist fairy tale. Director Garry Marshall wisely saw Roberts’ Vivian, not Richard Gere’s rich-guy Edward, as the real Prince Charming here: The weary tycoon constantly reminds his special lady friend to stop fidgeting while she constantly reminds him that money can’t buy everything. And damned if we’re not rooting for their connection to outlast six days, a lousy $3,000 and that one spoony Roxette song. PR

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Tracy Camilla Johns, Redmond Hicks She's Gotta Have It - 1986
33

‘She’s Gotta Have It’ (1986)

Young, hungry Brooklyn filmmaker Spike Lee defied preconceived notions about what “indie movies” and “black movies” were supposed to be, circa 1986 — and then, for good measure, he tossed out the rom-com playbook too. In his debut feature, Tracy Camilla Johns is a confident artist juggling three boyfriends: a brainy yuppie (Tommy Redmond Hicks), a macho model (John Canada Terrell) and a fast-talking bike-messenger (Lee). The director uses this offbeat love quadrangle as a frame and fills it with a poetry reading, a musical number, some unabashed erotica, a little stand-up comedy, and scene after scene that celebrates being young, African-American and sexually active in a culturally flourishing New York. NM

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Tootsie,  Dustin Hoffman
32

‘Tootsie’ (1982)

Infamous perfectionist Dustin Hoffman plays infamous perfectionist Michael Dorsey, an unemployable New York actor. Out of desperation, he dresses up as a woman to land a job on a soap opera, which only becomes more complicated when he falls for his costar Julie (Jessica Lange) and has to keep up the ruse. Aided by a killer ensemble cast that includes director Sydney Pollack (as an exasperated agent), Teri Garr and Bill Murray, it’s a very grownup romance about gender roles circa 1982 and stripping away your defenses in order to be truly vulnerable. Or, as Pollack explained it at the time, “If … a man puts on a dress, he’d better become a better man for it.” TG

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Adam Sandler- Punch Drunk Love - 2002
31

‘Punch-Drunk Love’ (2002)

Paul Thomas Anderson decides he’s going to make … an Adam Sandler comedy. Maybe you assumed the end result would be an unholy cross between Billy Madison and Boogie Nights; what you got, however, was one of the sweetest, most romantic (and rage-filled) movies that either men have done to date. As a plunger salesman, Sandler stalks around in a blue suit, suffering the aggravations of his sisters. But then he finds a woman (Emily Watson) who recognizes the childlike sweetness at his core. They’re a curious duo, considering he’s an eccentric with anger-management issues and an obsession over a pudding promotion, while she’s a wallflower who has every reason to fear him. Yet Punch-Drunk Love not only finds the humor in this match; it also puts them on their own lovestruck wavelength. ST

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Sabrina - 1954Humphrey Bogart, Audrey Hepburn
30

‘Sabrina’ (1954)

Humphrey Bogart, rom-com star? Sure, the man gave good banter with Lauren Bacall, but who would cast him opposite Audrey Hepburn and William Holden in a light, breezy love-triangle comedy? Billy Wilder saw something in Bogie that the rest of us did not, apparently, and thank god he did. The Roman Holiday actress plays the daughter of a rich family’s chauffeur, who’s pined for the family cad (Holden, natch) since you was a wee lass. After returning from Paris and looking like — well, like Audrey Hepburn in 1954 — the womanizer goes full Tex-Avery-wolf-eyes for her. His brother (Bogart) doesn’t want the young woman’s heart broken, so he pretends he’s in love with her … only to find that he doesn’t need to pretend after a while. Just watch this scene. The duo go together like oil and vinegar. DF

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James Gandolfini, Julia Louis-Dreyfus
29

‘Enough Said’ (2013)

Tony Soprano as a romantic lead? ‘Nuff said. Nicole Holofcener made us see James Gandolfini in a different light with this quietly moving film, co-starring Julia Louis-Dreyfus as a massage therapist who learns the man she’s seeing is the ex-husband of her new client (Catherine Keener). Holofcener has a soft touch with even the spikiest material, making it feel lived-in and comfortable, and Enough Said might be the coziest of all her films. It’s not that often that we get a rom-com featuring middle-aged characters, and there’s a real tenderness that Holofcener evokes here, capturing the soft side of Gandolfini in a genuinely sweet film. KW

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Spencer Tracy, Katharine HepburnWoman Of The Year - 1942
28

‘Woman of the Year’ (1942)

When Tracy Met Hepburn: From the moment his sportswriter and her political columnist lock eyes on each other in their editor’s office, you can practically feel the electric charge being exchanged between these two actors. George Stevens’ battle-of-the-sexes showdown was the first of nine movies that Spencer Tracy and Katharine Hepburn would make together, and it immediately established the template for their comedies: He was a salt-of-the-earth rascal; she was a sometimes snobbish, always sophisticated lady; together, they were a near-perfect screen couple. No offense to Adam’s Rib or Pat and Mike, but this initial pairing is still the best example of why they’re a legendary rom-com duo. Not even that seriously retrograde ending can ruin it. DF

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Tom Cruise Jerry Maguire - 1996
27

‘Jerry Maguire’ (1996)

In telling the story of a down-on-his-luck sports agent (Tom Cruise) desperately clinging to the only loyal people in his life — his client (Cuba Gooding Jr.) and employee/love interest (Renée Zellweger) — writer-director Cameron Crowe once again plumbs the psyche for all its damage and worth. (See also: Say Anything.) Cruise’s Jerry, a big shot with a sudden case of conscience, treats everyone else like a supporting player. He’s needy, opportunistic … and, in short, human. And then there’s The Speech — you know, the “you complete me” one. It’s a classic rom-com Hail-Mary pass of a soliloquy. But to be honest, everybody here — including the then-undersung Regina King — had us at hello. PR

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Notting Hill, Julia Roberts, Hugh GrantCredit Moviestore/REX/Shutterstock
26

‘Notting Hill’ (1999)

Pairing Julia Roberts and Hugh Grant may seem like the union of rom-com royalty, complete with a script by Richard Curtis (Four Weddings and a Funeral) — but this is the sort of movie that revels in bringing its stars down to earth. In order to get to a place where Roberts is “just a girl, standing in front of a boy, asking him to love her,” Notting Hill plays off her A-list, America’s-Sweetheart image beautifully, as a conflict between the glamour and guardedness of being among the Hollywood elite and a longing for the simpler pleasures of being human. Grant bats his eyelids as charmingly as ever here; his sincerity and gentle wit make for a perfect grounding force. ST

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Noah Centineo and Lana Condor in To All The Boys I've Loved Before
25

‘To All the Boys I’ve Loved Before’ (2018)

From straight-to-Netflix release to one of the most swoonworthy movies of 2018 — give it up for this rom-com based on Jenny Han’s young adult novel, in which shy teen Lara Jean Covey (Lana Condor) fake-dates 11th grade heartthrob Peter Kavinsky (Noah Centineo) for the kind of complicated reasons endemic to any great high school farce. Not only does To All the Boys set a precedent for teen romantic comedies with non-white leads (Lara Jean and her family are half-Korean), but it also finds the template for a new era of male romantic lead: a guy who, rather than being a charming alpha asshole who must be reformed, is just a supernice, chill dude right from the get-go. JS

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Bud Cort, Ruth Gordon in Harold and Maude - 1971
24

‘Harold and Maude’ (1971)

Sure, it can be hard to have a relationship when there’s a 50-plus age gap between the two participants — and you might say that one party’s endless suicide attempts would be an obstacle to a happily-ever-after ending as well. But if Hal Ashby’s cult classic proves nothing else, it’s that anything is possible when you find your soul mate. Bud Cort is Harold, a death-obsessed rich kid. Ruth Gordon is Maude, a septuagenarian woman who doubles as a human sunflower. They meet at a funeral — of course they do! — and form one of the screen’s greatest anti-conformist couples ever. It’s the romantic comedy for those that prefer their quirk with an extra side of offbeat, a life-affirming story that reminds you that every pot has a lid (even the warped ones) and a joyous celebration of the power of connection. If you want to be free, be free. DF

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Hugh Grant, Andie Macdowell - Four Weddings and A Funeral - 1994
23

‘Four Weddings and a Funeral’ (1994)

Could the modern romantic comedy even exist without Hugh Grant? In Four Weddings and a Funeral, he redefined the “charming British suitor” type, replacing the old-fashioned suave sophistication with a fumbling humanity. And with their star’s help, screenwriter Richard Curtis and director Mike Newell delivered a surprise box-office smash, with a story about a group of well-to-do, thirtysomething Englishfolk reluctantly confronting the seriousness of real life. As Grant’s stammering nice guy weighs his many romantic options — Should he end up with Andie MacDowell and Kristin Scott Thomas? And was there really any doubt whom he would pick before the final credits? — his quest for love doubles as the story of an overgrown schoolboy growing up. NM

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Editorial use only. No book cover usage.Mandatory Credit: Photo by Bruce Mcbroom/Tri-Star/Kobal/REX/Shutterstock (5881296j)Meg RyanSleepless In Seattle - 1993Director: Nora EphronTri-Star PicturesUSAScene StillComedyNuits blanches à Seattle
22

‘Sleepless in Seattle’ (1993)

It’s the rare rom-com that has the audacity to keep its two would-be lovers apart until the closing moments of the movie, but leave it to her royal highness Nora Ephron to make the gimmick work — and work brilliantly. The setup is pure Nineties missed connection: On Christmas Eve, newspaper reporter Annie (Meg Ryan) finds herself drawn to a widower (Tom Hanks) who she hears on a call-in radio show. She slowly becomes obsessed with tracking him down and arranging an Affair to Remember-inspired meeting — despite the fact that he lives clear on the other side of the country and doesn’t even know she exists. As Sleepless in Seattle plays out, the viewer becomes as invested in the idea of these two folks finding each other as Annie is. The fact that we’re essentially watching the story of a stalker pursuing her prey and rooting for her the whole way is a testament to both Ephron’s writing and to Ryan’s unassailable charm. JS

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Editorial use only. No book cover usage.Mandatory Credit: Photo by Paramount/Kobal/REX/Shutterstock (5884983f)Jon Cryer, Molly RingwaldPretty In Pink - 1986Director: Howard DeutchParamountUSAScene StillDramaRose Bonbon
21

‘Pretty in Pink’ (1986)

John Hughes made teen comedies that had romantic elements in them (it was possible to forget at times that Sixteen Candles revolved around Sam pining for Jake Ryan amidst all the nerd shenanigans and that cringeworthy Long Duk Dong thing). But this Hughes-penned movie — with Howard Deutch in the director’s chair — found just the right balance of funny, funky, heart-meltingly swoony and sweet. Wrong-side-of-the-tracks student Andie Walsh (Molly Ringwald, iconic) could never attract the attention of a rich prep like Blaine McDonaugh (Andrew McCarthy). What would their equally snobbish friends think? The ending is still enough to choke you up. And whenever things threaten to get too heavy, along comes Ducky in all his thrift-store-outfit, Otis-Redding-singing glory to crack you up. God bless you, Jon Cryer. DF

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Bringing Up Baby,  Katharine Hepburn,  Cary Grant
20

‘Bringing Up Baby’ (1938)

Howard Hawks’ genuinely uproarious, innuendo-filled romp was a bomb upon release — a piece of trivia that only adds to the merits of this screwball masterpiece. Cary Grant’s bumbling Dr. David Huxley just wants one last bone [ahem] to build his brontosaurus. Instead, he’s pushed to the brink of sanity at breakneck speed by Katharine Hepburn’s irrepressible, scatterbrained heiress Susan Vance, who hopes to save him from a marriage that promises to be dustier than a dinosaur fossil. A simmering frustration leads, naturally, to love — but not before they spend half their time together chasing animals, from an impish terrier to a leopard named Baby (the film long predated our current mania for furry thespians). PR

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Editorial use only. No book cover usage.Mandatory Credit: Photo by 20th Century Fox/Kobal/REX/Shutterstock (5883616c)Melanie Griffith, Harrison FordWorking Girl - 1988Director: Mike Nichols20th Century FoxUSAScene StillComedyWorking Girl / Quand les femmes s'en mêlent
19

‘Working Girl’ (1988)

Melanie Griffith has never been better than in Mike Nichols’ “fake it ’til you make it” tale as spunky Staten Island secretary Tess McGill, who makes her big career move when her snooty boss, Katharine (Sigourney Weaver) steals her big idea and then breaks a leg skiing. It’s a slice of Eighties Wall Street excess that captures the culture in exacting detail, from the secretaries commuting in sneakers to the debauched workplace behavior. It’s also a genuinely sexy movie that only gets sexier as Tess puts on an air of cool confidence to go after the career she deserves and the man she wants — Harrison Ford in his prime as big-shot mergers-and-acquisitions honcho Jack. KW

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'ROMAN HOLIDAY' WITH 1953, AUDREY HEPBURN, GREGORY PECK
18

‘Roman Holiday’ (1953)

Being a princess is hard work, as Audrey Hepburn’s visiting royal ambassador will tell you. What she would not give to see the sights of Rome on her own like an anonymous civilian! So her highness plays hooky from her duties and pretends to be your average tourist. Enter reporter Gregory Peck, who takes kindness on this lost stranger … until he realizes who she is and smells a helluva scoop. You can keep your Breakfast at Tiffany’s — for us, this is the ultimate Hepburn movie, full of grace, wit and some truly glorious footage of two movie stars tooling around the Italian city on a moped. Ask any visitor who’s ever stuck their hand inside the Bocca della Verità — the film is genuinely iconic. DF

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Ben Stiller, Cameron Diaz There's Something About Mary - 1998
17

‘There’s Something About Mary’ (1998)

Just what nobody expected in the summer of 1998: a romance from the Farrelly Brothers, in the wake of Dumb and Dumber. There’s Something About Mary was a wildly offensive feast of gross-out gags, with Cameron Diaz famously using some of Ben Stiller’s bodily fluids as hair gel. But hidden in all the sleaze was a surprisingly deft parable about trust and security, with sharp flirtatious banter. (Ben: “I think I’ll quit while I’m ahead.” Cameron: “You’re not that far ahead.”) Punk-rock cult hero Jonathan Richman plays the narrator, showing up with his guitar whenever somebody needs a song. There’s also Matt Dillon, Chris Elliott, Sarah Silverman, “Build Me Up Buttercup” and a pre-dick-pic Brett Favre. RS

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'SOMETHING WILD' WITH 1986, JEFF DANIEL, MELANIE GRIFFITH
16

‘Something Wild’ (1986)

The pairing of a square guy and a free-spirited girl — it’s always a rom-com home run, right? Few movies have taken that notion to weirder, wilder places than this Jonathan Demme effort, in which Jeff Daniels’ uptight banker meets Melanie Griffith’s exotic rebel after attempting a dine-and-dash. She not only recognizes a guy who’s ready to unwind a little; this dream bohemian also ropes him into playing the role of a respectable type at her high-school reunion. Then their road trip gets considerably crazier when her psychotic ex-boyfriend (Ray Liotta) comes into the picture. There’s a naughty energy that keeps things going even when the film takes a darker turn — credit the cracked chemistry between Daniels and Griffith. We wish Demme had made more movies with them as a duo. ST

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The Lady Eve,  Henry Fonda,  Barbara Stanwyck
15

‘The Lady Eve’ (1941)

No old-school Hollywood couple can match the acid-to-alkaline chemistry of Barbara Stanwyck and Henry Fonda. She’s a con artist aboard a cruise ship who sets her sights on big game: Fonda, a mild-mannered reptile scholar and heir to the Pike Ale fortune. (“The ale that won for Yale!”) The gold diggers are after him — as Stanwyck sneers, “Every Jane in the room is giving him the thermometer” — but no woman can turn his head from his books and his pet snake… until Stanwyck steps in to destroy his life. Preston Sturges crams this classic with nonstop barbs (“Why Hopsie — you oughta be kept in a cage!”) in a screenplay where every line is endlessly quotable, right down to the final four words. Positively the same dame! RS

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The Princess Bride,  Cary Elwes,  Robin Wright Penn
14

‘The Princess Bride’ (1987)

If you grew up in the Eighties, few phrases in the English language are a faster shorthand for heart-fluttering romance than “As you wish.” Rom-com sensei Rob Reiner created a masterpiece that has something for everybody: high fantasy, wry comedy, kick-ass swordfights, canny political commentary and, of course, sigh-inducing true love. (Or rather, twue wuv.) As we follow reluctant damsel Buttercup (Robin Wright) and farmboy-turned-pirate Westley (Cary Elwes) up the Cliffs of Insanity, through the Fire Swamp and to the very edge of death, we’re simultaneously rooting for our lovers to win the day and chuckling at the knowingly trope-tweaking silliness of it all. Plus unlike the ailing grandson (Fred Savage) in the framing story, we are most definitely not grossed out by the kissing parts. JS

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Pillow Talk,  Doris Day,  Rock Hudson
13

‘Pillow Talk’ (1959)

Rock Hudson and Doris Day started their winning onscreen collaboration here, adeptly playing into their public personas: He’s Brad, a smug womanizer who shares a party line with Jan, a fussy, prudish career gal who doesn’t have time for love. Thanks to some wonderfully convoluted circumstances, however, a spark develops between them — although he has to disguise his voice so she doesn’t realize he’s the jerk on her phone. It’s not just the concept of a party line that makes Pillow Talk old-fashioned — its gender politics are rigidly mid-century, white-picket-fence conservative. But that cultural parochialism only gives the film’s subversive sexiness and combustible chemistry extra naughty delight. Underneath all that squeaky-clean innocence, there’s a whole lot of thirstiness. TG

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It Happened One Night,  Clark Gable,  Claudette Colbert
12

‘It Happened One Night’ (1934)

And down come the walls of Jericho! Arguably the Rosetta stone of rom-coms, Frank Capra’s Oscar-winning behemoth pairs one hoity-toity heiress (Claudette Colbert) and one desperate investigative journalist (Clark Gable, singlehandedly killing the undershirt business) on one long, crazy road trip. The fact that this farce skirted in right under the wire before the Hays Code started getting rigid on risque material lends an extra layer of erotic friction to the laughs — not to mention the fact that the two leads were at their sexiest and their funniest in 1934. (All apologies, The Palm Beach Story.) Everyone remembers the hitchhiking scene, but personally, we stan for the sequence in which Gable carries Colbert across a river over his shoulder. (“Now you take Abraham Lincoln … a natural-born piggy-backer!”) Still hilarious, still hot. DF

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Woody Allen, Diane Keaton Annie Hall - 1977
11

‘Annie Hall’ (1977)

Woody Allen is so central to his films’ appeal — which is why the dark cloud hovering over the writer-director-star makes it difficult now to fully access what is so poignant, hilarious, hip and thoughtful about this unlikely Best Picture-winner that radically modernized the romantic comedy. This story of a neurotic comic (Allen) and an aspiring singer (Diane Keaton) isn’t just about how people fall in love — it’s about how they fall out of love, drift apart, realize that their once-hot passion will eventually dissolve into an enduring, distant fondness (if they’re lucky). Annie Hall endures as one of the most honest portraits of attraction’s ebb and flow, embodied in Keaton’s unimpeachable performance as a budding artist who eventually learns she doesn’t need an insecure man’s approval to love herself. TG

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Editorial use only. No book cover usage.Mandatory Credit: Photo by Louis Goldman/Columbia/Kobal/REX/Shutterstock (5883080l)Bill Murray, Andie MacdowellGroundhog Day - 1993Director: Harold RamisColumbia PicturesUSAScene StillComedyUn jour sans fin
10

‘Groundhog Day’ (1993)

The existential quest for self-betterment has never been more hilariously, nor more movingly, teased out than in this Harold Ramis classic, which could be subtitled Phil Connors in the Bardo. As Bill Murray’s grouchy weatherman is forced to endlessly relive the same frigid February day in the limbo known as Punxsutawney, PA, he moves from irritation to nihilism to depression to, finally, the earnest pursuit of true love. Amid our man’s meanderings on that infinite winter’s day, the true pleasure of Groundhog Day is watching him fall for — and then work to make himself worthy of — his producer Rita (Andie MacDowell). What’s more romantic than a guy learning to carve ice sculptures for you? JS

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Editorial use onlyMandatory Credit: Photo by Snap/REX/Shutterstock (390851kc)FILM STILLS OF 'BULL DURHAM' WITH 1988, KEVIN COSTNER, EMBRACE, KISSING, ROMANCE, SUSAN SARANDON IN 1988VARIOUS
9

‘Bull Durham’ (1988)

The thing about baseball is, when you’re evaluating a fastball pitcher … wait, come back! Bull Durham was a breakthrough in the Eighties — a sports movie that doubled as a date flick. Susan Sarandon stars as an intellectual North Carolina baseball fan with a thing for handsome minor-league prospects. She spends the movie juggling a couple of conspicuously younger suitors: catcher Kevin Costner and pitcher Tim Robbins. It finally made a star out of Sarandon, who’d been kicking around Hollywood for a couple of decades without getting her chance to shine as a wise-cracking feminist leading woman. And Costner got a career-making speech in praise of “long, slow, deep, soft, wet kisses that last three days.” RS

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The Apartment: Jack Lemmon, Shirley MacLaine
8

‘The Apartment’ (1960)

As C.C. Baxter, the most put-upon of all his put-upon characters, Jack Lemmon plays a white-collar drone so ineffectual that he loans out his apartment for his boss’s extramarital dalliances, pining for some up-the-corporate-ladder payout down the line. Which is why he shares a kinship with Shirley MacLaine’s elevator operator, who’s also getting strung along by a two-timing executive. But it’s the contrast between his mania and her melancholy that holds Billy Wilder’s brilliant, winsome office comedy in balance — as if they’re tugging each other in the right direction. Just watch how Lemmon clowns around in a “junior executive” bowler hat and takes MacLaine’s holiday blues away. Out of miserable circumstances, the two lonelyhearts bond in their humor, resilience and mutual insistence on dignity. It’s a match made in heaven, one floor at a time. ST

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Say Anything: Ione Skye, John Cusack 1989
7

‘Say Anything’ (1989)

One of the most tender teen comedies in the canon: Lloyd Dobler (John Cusack) set the stage for high-school boys to be more than a heap of hormones. Seriously, who could have played this sweet, boom box-toting antidote to dude-bros, i.e. the knucklheads hanging out at the Gas ‘n’ Sip pontificating about the opposite sex? Described as “basic” by brainy, beautiful Diane Court (Ione Skye), our underachieving hero nonetheless wins her heart … only to get his broken. Both Skye and Cusack bring such raw, physical emotion to their performances that the story easily evolves beyond strict rom-com. It’s still funny — just yell “You. Must. CHILL!” in your best Dobler voice and try not laugh. But ultimately, it’s their young love that’s as satisfying as the ding after a plane takes flight. PR

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Nicolas Cage, Cher in Moonstruck (1987)
6

‘Moonstruck’ (1987)

Casting “crazy” Nicolas Cage as a romantic lead may seem absolutely loony. But that’s partially why Moonstruck still feels so charming: It’s a mature love story that explains why it’s sometimes right to fall for Mr. Wrong. Cher is Loretta Castorini, a cautious Italian-American widow all set to get remarried to a bland fella. Then guess who has her heart stolen by his surly one-handed sibling, played by you-know-who? And who knew these actors would fit so well together? It’s a movie that has both the ring of seen-it-all truth and the atmosphere of a fairy tale — like a Dean Martin song come to life. “Snap out of it!” NM

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Paul Rudd,  Alicia Silverstone in CLUELESS
5

‘Clueless’ (1995)

Writer-director Amy Heckerling didn’t set out to reinvent Jane Austen — Clueless was supposed to be about the adorable narcissism of Beverly Hills teens. Then she realized that the rest of America might not find these super-rich kiddos so cute, so she borrowed the moralistic plot of Austen’s 1815 novel Emma. And in a second stroke of genius, she cast the preternaturally cheery Alicia Silverstone as her meddling heroine, who plays matchmaker and makeover expert for her friends, yet can’t spot her own flaws — until she finds someone to love her, that is. (Hi there, Paul Rudd!) The result … well, you know what the result is. It’s a modern teen-movie classic, a Hall-of-Fame romantic comedy and the film most responsible for adding “As if!” to the lexicon. And this story’s truly timeless, even in a 1995 world filled with enormous cell phones and spontaneous appearances by the Mighty Mighty Bosstones. NM

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Rosalind Russell, Cary Grant in His Girl Friday - 1940
4

‘His Girl Friday’ (1940)

In this corner: Cary Grant, the world’s most dashing newspaper editor. In that corner: Rosalind Russell, his ace reporter, who also happens to be his ex-wife. In a few days, she’s getting married to bland ol’ Ralph Bellamy (right!) and leaving the news racket forever — but first, these two have one last big story to break. Howard Hawks adapted the play The Front Page, turning the reporter into a woman, with Russell yelling endearments like “Now get this, you double-crossing chimpanzee!” It remains one of the speediest comedies ever made — Hawks wrote overlapping dialogue to better mimic the way people talk, then asked his actors to read the lines twice as fast as usual. In the days before Robert Altman or Veep, no movie crammed in so many rapid-fire insults per minute. RS

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Broadcast News,  William Hurt,  Holly Hunter
3

‘Broadcast News’ (1987)

Why does love got to be so sad? That question haunts James L. Brooks’ very funny, incredibly bittersweet look at the vagaries of romance and TV journalism. The writer-director crafted what he later called a film about “three people who lost their last shot at intimacy,” presenting a romantic triangle consisting of a neurotic reporter (Albert Brooks), the news producer he secretly loves (Holly Hunter) and the shallow, handsome broadcaster she should despise but instead finds charming (William Hurt). Personal and professional ethics are at the heart of Broadcast News, but this is also a wise film about the impossibility of juggling love and career. Its ending may not technically be “happy,” but it’s piercingly true. And you simply can’t beat a line like “Wouldn’t this be a great world if insecurity and desperation made us more attractive?” TG

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The Philadelphia Story,  Cary Grant,  Katharine Hepburn
2

‘The Philadelphia Story’ (1940)

“Either I’m gonna sock you or you’re gonna sock me!” “Shall we toss a coin?!” The Philadelphia Story’s verbal pyrotechnics are merely part of the brilliance of this 1940 Oscar winner, in which dejected ex-husband C.K. Dexter Haven (Cary Grant) conspires with journalist Mike Connor (Jimmy Stewart) to crash the glitzy wedding of Haven’s former wife Tracy Samantha Lord (Katharine Hepburn). Fans love the biting back-and-forth dialogue among this trio of combatants — a scenario that only gets more complicated once she starts falling for both men. But beyond the witty repartee and impossibly beautiful actors, director George Cukor skillfully underlines the poignancy of people using love as a quick fix for deeper insecurities and gnawing dissatisfactions. All that, plus a pitch-perfect urbane tone, airtight plotting and the best flirty effervescence the Golden Age of Hollywood could buy. Pure rom-com bliss. TG

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Editorial use only. No book cover usage.Mandatory Credit: Photo by Snap Stills/REX/Shutterstock (1933418e)Meg Ryan, Billy CrystalWhen Harry Met Sally - 1989
1

‘When Harry Met Sally’ (1989)

The Attraction Theory. The bookstore encounter. The New Year’s Eve admission of love. The vignettes of older couples recounting their relationship stories. “You made a woman meow?!” The split screen phone call involving Carrie Fisher and Bruno Kirby’s best friends. The deli scene — dear god, that deli scene. Chances are good that when you hear the phrase “rom-com,” Rob Reiner’s movie — about two longtime acquaintances who finally realize the only people that are truly right for them is each other — was the first title you thought of. Yes, it owes a good deal to Annie Hall in its tenor and tone, but what Billy Crystal and Meg Ryan do with these roles is sui generis; it’s a one-of-a-kind alchemy. And anyone who does not think Nora Ephron was as great a screenwriter as she was an essayist simply isn’t paying attention. It is the one rom-com to rule them all, a perfect distillation of the form. We’ll always have what they’re having. DF

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