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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.”

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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