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The 50 best romcoms of all time

Love – it’s a funny old game. Or at least it is in these films. Here's Time Out's definitive list of the 50 best romcoms.

By Dave Calhoun, Cath Clarke, Tom Huddleston, Kate Lloyd, Phil de Semlyen and Alim Kheraj |

Like cargo pants and saying 'as if!' to people, romcoms were huge in the '90s but have fallen sadly out of fashion in recent years. Because when they’re good, they’re often very, very good. Even the staunchest skeptic would need a heart of stone not to feel the warm and fuzzies when confronted with these 50 genre gems.

From Nora Ephron classics to Richard Curtis movies that are so-very-British (and so-very-funny), we've put together 50 of the most hilarious romantic comedies and bittersweet romances that'll leave a lump in your throat and tears rolling down your cheeks.

RECOMMENDED: The 100 best romantic movies 

The 50 best romcoms of all time: 50-41

Notting Hill, best romcoms
Film, Comedy

Notting Hill (1999)

'After all... I’m just a girl, standing in front of a boy, asking him to love her.'

'Notting Hill' might be schmaltzy and incredibly twee, but there's something eternally charming about '90s Hugh Grant, all floppy hair and stuttering awkwardness. Here, unbeknownst to him, he falls for an American movie star, played by Julia Roberts, after a chance meeting in his travel bookshop. Their compatibility is questioned, with the will-they-won't-they culminating in a hilarious dash through London for the film's great romantic gesture.

Buy, rent or watch 'Notting Hill'

It’s Complicated, best romcoms
Film, Comedy

It’s Complicated (2009)

‘Here comes your ex-husband. Uh-oh, not the best time to be feeling groovy!’

It was refreshing to see three older actors – Meryl Streep, Alec Baldwin, Steve Martin – dominating this story of a well-heeled suburban woman and matriarch caught between her charming but hard-to-trust ex (Baldwin) and a potential sweet new love (Martin).

Buy, rent or watch 'It's Complicated'

Muriel’s Wedding, best romcoms
Film, Comedy

Muriel’s Wedding (1994)

‘You’re terrible, Muriel.’

This Australian movie seems frothy on the surface, but its story about an ugly duckling who's obsessed with Abba also deals with darker issues like psychological abuse and low self-esteem.

While You Were Sleeping, best romcoms
Film, Comedy

While You Were Sleeping (1995)

‘You don’t have to walk me home.’ ‘You block the wind.’

There’s something comforting about basking in the comfort of clichés, and this sugary sweet movie is full of them. Sandra Bullock plays a commuter who saves a guy from falling in front of a subway train then falls for his brother. It’s very sentimental, but in a good way. 

Buy, rent or watch 'While You Were Sleeping'

Crazy Stupid Love
Ben Glass / Warner Bros. Entertainment Inc.
Film, Comedy

Crazy, Stupid, Love (2011)

"F**k! Seriously? It's like you're photoshopped!"

Emma Stone, Ryan Gosling, Steve Carell and Julianne Moore star in this bitingly funny modern romance about what life looks like after a marital crisis. This big-named cast deftly steer this film from satire to farce, with an ending that'll definitely hit you in the feels.

Buy, rent or watch 'Crazy, Stupid, Love'

Sleepless in Seattle, best romcoms
Film, Comedy

Sleepless in Seattle (1993)

‘You don’t want to be in love. You want to be in love in a movie.’

Written by Nora Ephron, the brains behind ‘When Harry Met Sally...’, this weepy comedy was a massive box office hit in the early ’90s. It stars Tom Hanks as a heartbroken widower who falls in love with a girl (Meg Ryan) on the other side of America.

Buy, rent or watch 'Sleepless in Seattle'

Roxanne, best romcoms
Film, Comedy

Roxanne (1987)

‘Finally, a man who can satisfy two women at the same time!’

Steve Martin’s finest hour as a romantic lead – which is impressive, considering he’s saddled with a four-inch prosthetic conk. Wittily reinventing ‘Cyrano De Bergerac’, this graceful comedy has all kinds of fun exploring the complex nature of desire, and comes out firmly on the side of the unconventionally attractive.

Buy, rent or watch 'Roxanne'

The 50 best romcoms of all time: 40-31

Something Wild, best romcoms

Something Wild (1986)

‘Charlie, attempt to be cool.’

Jonathan Demme’s brilliantly unpredictable comedy starts out as old-school screwball with an emphasis on the screw, as street-smart Melanie Griffith sweeps straight-laced Jeff Daniels off to a motel for a night of passion. But when she takes him home to meet the folks – and the psychotic ex – things take a deliciously dark turn.

Buy, rent or watch 'Something Wild'

Jamón, Jamón, best romcoms

Jamón, Jamón (1992)

‘My son will not go out with that girl. Her mother’s a whore!’

Blending sex, love, humour and cooked meat (the title means ‘Ham, Ham’, and refers to the supposed flavour of the heroine’s nipples), this giddily erotic Spanish comedy launched the careers of both Penélope Cruz and Javier Bardem.

Buy, rent or watch 'Jamón, Jamón'

Heartbeats, best romcoms
Film, Drama

Heartbeats (2010)

‘I love you. I really want to kiss you. I don’t know why I’m telling you this.’

He’s now one of the best-known young directors in the world, but French-Canadian Xavier Dolan was a 21-year-old outsider when he made this smart, artsy tale of two friends – a girl and a guy – who both fall in love with the same person.

Buy, rent or watch 'Heartbeats'

Gregory’s Girl, best romcoms
Film, Comedy

Gregory’s Girl (1981)

‘Hard work being in love, eh? Especially when you don’t know which girl it is.’

Glasgow – city of romance? Perhaps not, but Bill Forsyth’s timeless story of one lanky, lovelorn teenager’s fixation on the new girl in school still manages to be both dryly hilarious and heartwarmingly sentimental.

Buy, rent or watch 'Gregory's Girl'

I Married a Witch, best romcoms
Film, Comedy

I Married a Witch (1942)

‘Goodbye, Jennifer. Be a bad girl.’

Veronica Lake may not be a household name these days, but in the golden age of Hollywood her unique platinum-blonde locks were recognised all over the world. This hilarious supernatural romp isn’t quite her best movie – that’s ‘Sullivan’s Travels’ – but it is her finest hour as a louchely comic romantic lead. The film would be reworked for TV as the long-running sitcom ‘Bewitched’.

Top Hat, best romcoms
Film, Drama

Top Hat (1935)

‘In dealing with a girl or horse, one just lets nature take its course.’

This musical comedy is inarguably one of Fred Astaire and Ginger Rogers' finest. The humour's charming, the art deco set is stunning and there's tangible sexual tension in the dance scenes.

Buy, rent or watch 'Top Hat'

The 50 best romcoms of all time: 30-21

The Wedding Singer, best romcoms

The Wedding Singer (1998)

‘I know you’re shy and I know you’ve been hurt, so I’m going to make this really easy on you. If you come upstairs, you’re gonna get laid.’

While the title of this film suggests it probably stars Julia Roberts and/or Hugh Grant, this silly romcom actually stars Adam Sandler and a very sweet Drew Barrymore. He’s a broken-hearted wedding singer, she’s a waitress who’s engaged to a douchebag. They fall in love, obvs. 

The Purple Rose of Cairo, best romcoms
Film, Comedy

The Purple Rose of Cairo (1985)

‘I just met a wonderful new man. He’s fictional but you can’t have everything.’

This 1930s-set Woody Allen film tells of a woman (Mia Farrow) who falls in love with a character (Jeff Daniels) who steps out of the screen at the cinema, only to find herself also being wooed by the actor playing said character (also Jeff Daniels). It’s one of Allen’s most original stories.

Buy, rent or watch 'The Purple Rose of Cairo'

But I’m a Cheerleader, best romcoms

But I’m a Cheerleader (1999)

‘I thought it was just an act, but you really are sweet as fucking pie, aren’t you?’

What’s that – a teen movie that challenges gender roles? Impossible! Natasha Lyonne (now famous from ‘Orange is the New Black’) plays a gay cheerleader sent to conversion camp to ‘cure’ her homosexuality only to fall in love with a fellow camper. This cult hit also stars Ru Paul. 

Say Anything, best romcoms

Say Anything (1989)

‘I gave her my heart, she gave me a pen.’

It’s the film that made high-schoolers think that standing on someone’s lawn holding a boombox was the ultimate declaration of love. A baby-faced John Cusack stars as a wannabe kick-boxer who falls for a straight-A student.

His Girl Friday, best romcoms
Film, Comedy

His Girl Friday (1940)

‘You’ve got an old fashioned idea divorce is something that lasts forever, till death do us part.’

The fastest and funniest screwball comedy of them all. Rosalind Russell is the ace reporter whose lethally charming ex-husband (Cary Grant) just won’t take no for answer. Will she marry her dull-as-ditchwater fiancé or go back to Cary? What do you think?

Buy, rent or watch 'His Girl Friday'

Four Weddings and a Funeral, best romcoms
Film, Comedy

Four Weddings and a Funeral (1994)

'Basically you're saying marriage is just a way of getting out of an embarrassing pause in conversation.'

Boy meets girl. Well, actually, boy meets several girls and, um, well, things, erm, get fairly awkward. Then boy meets the girl and after much flirting, some killer gags and Hugh Grant at his most charmingly bumbling and foppish… well, you know the rest. A strong supporting cast and a tear-jerking funeral scene give it all extra heart.

Buy, rent or watch 'Four Weddings and a Funeral'

The Apartment, best romcoms
Film, Comedy

The Apartment (1960)

‘When you’re in love with a married man, you shouldn’t wear mascara.’

Talk about office politics. Jack Lemmon plays a white-collar worker pimping his flat to his bosses, who use it for their illicit affairs (well, it’s cheaper than a motel). Shirley MacLaine plays the lift girl he has his eye on. ‘The Apartment’ may be bitter and nihilistic, but its heart is firmly in the right place.

Buy, rent or watch 'The Apartment'

Guys and Dolls, best romcoms
Film, Drama

Guys and Dolls (1955)

‘Your eyes are the eyes of a man who’s in love, may they gaze evermore into mine…’

Marlon Brando and Frank Sinatra star in the coolest musical on the block. The duo play NYC hustlers who lay bets on whether Brando can seduce pious Salvation Army girl Jean Simmons. It’s the movie that brought us the song ‘Luck Be A Lady’, so that’s surely reason enough to watch it. 

The 50 best romcoms of all time: 20-11

The Lady Eve, best romcoms
Film, Comedy

The Lady Eve (1941)

‘I’ve got some unfinished business with him – I need him like the axe needs the turkey.’

Henry Fonda is a fabulously rich snake expert who falls into the clutches of sexy gold-digger Barbara Stanwyck in this ferociously funny battle of the sexes. A glittering screwball comedy from the master of the form, Preston Sturges, ‘The Lady Eve’ is near perfect.

Buy, rent or watch 'The Lady Eve'

Before Sunrise, best romcoms

Before Sunrise (1995)

‘Isn’t everything we do in life a way to be loved a little more?’

If you liked ‘Boyhood’, why not take a trip back to the early days of writer-director Richard Linklater and star Ethan Hawke’s careers: in this loose, walking-and-talking romance, Hawke plays an American in Europe who has an intense one-night affair of the heart with a French fellow traveller (Julie Delpy).

Buy, rent or watch 'Before Sunrise'

I Know Where I’m Going!, best romcoms

I Know Where I’m Going! (1947)

‘They’re not poor, they just haven’t got money.’

A headstrong young woman (Wendy Hiller) knows exactly what she wants: she’s heading to the Hebrides to marry a reclusive tycoon twice her age. But nature, wise locals and Roger Livesey as a young naval officer get in the way in this near-perfect loch-side romance.

Smiles of a Summer Night, best romcoms
Film, Comedy

Smiles of a Summer Night (1955)

‘Men are horrible, vain and conceited. They have hair all over their bodies.’

Ingmar Bergman isn’t the first name that trips off the tongue when considering the great romcoms, but before he got all gloomy and existential the Swedish master turned out this hilarious and bawdy country-house farce.

The Shop Around the Corner, best romcoms

The Shop Around the Corner (1940)

‘I really wouldn’t care to scratch your surface, Mr Kralik, because I know exactly what I’d find. Instead of a heart, a handbag. Instead of a soul, a suitcase. And instead of an intellect, a cigarette lighter… which doesn’t work.’

It was loosely remade as ‘You’ve Got Mail’, but we urge you to check out the infinitely superior original, a tale of loathing turning to love between the employees of a glamorous department store in pre-war Budapest.

Buy, rent or watch 'The Shop Around the Corner'

Bringing Up Baby, best romcoms
Film, Comedy

Bringing Up Baby (1938)

‘It isn’t that I don’t like you, Susan, because, after all, in moments of quiet, I’m strangely drawn toward you. But – well, there haven’t been any quiet moments.’

Hepburn! Grant! Leopard! The ultimate screwball comedy, this story of a down-to-earth gal, a dippy scientist and a stray big cat named Baby is sheer, ridiculous fun from start to finish.

Pretty Woman, best romcoms
Film, Comedy

Pretty Woman (1990)

‘I want the fairy tale.’

With a plot laced with greed, sex and boxy suits, this Richard Gere-headed film is painfully ’80s, but in the best possible way. This is largely thanks to Julia Roberts spitting her witty lines with fiery intensity. 

Buy, rent or watch 'Pretty Woman'

Ninotchka, best romcoms
Film, Comedy

Ninotchka (1939)

‘I’m so happy, I’m so happy! Nobody can be so happy without being punished.’

‘Garbo Laughs!’ proclaimed the posters, advertising the fact that one of Hollywood’s most austere stars had made her first comedy. As a Soviet attaché who falls for a down-to-earth American businessman, Greta Garbo mocks her own ice-queen persona throughout this flawless political satire.

Buy, rent or watch 'Ninotchka'

Film, Comedy

The Big Sick (2017)

'So... to fully know I love someone, I have to cheat on them?'

Emily V. Gordon and Kumail Nanjiani, the real-life couple who penned this film, give us a Pakistani-American culture-shock romance that isn’t awash with clichés. We meet Emily (Zoe Kazan plays Gordon’s on-screen surrogate) and Kumail (Nanjiani playing a version of himself) just before Emily falls into a coma. Suddenly for Kumail, there’s heartache, hospitals and parents to deal with.

Buy, rent or watch 'The Big Sick'

Clueless, best romcoms
Film, Comedy

Clueless (1995)

‘Why should I listen to you, anyway? You’re a virgin who can’t drive.’

This satiric look at LA high school might be full of frenemies and makeovers, but at its heart, it’s a cute love story. Sure, it’s a slightly perverse tale of romance between Cher (Alicia Silverstone) and her step-brother (Paul Rudd), but it’s cute nonetheless.

Buy, rent or watch 'Clueless'

The 50 best romcoms of all time: top ten

Show Me Love, best romcoms

Show Me Love (1998)

‘Is it true you’re a lesbian? If you are I understand, ‘cause guys are so gross. I’m also going to be one, I think.’

This sweet and moving Swedish coming-of-age tale tells of two teenage girls, bored out of their minds by life in their small town, who gradually come to realise the best thing going for them is each other.

Punch-Drunk Love, best romcoms
Film, Comedy

Punch-Drunk Love (2002)

‘I have a love in my life. It makes me stronger than anything you can imagine.’

With its strange, dreamlike tone and moments of sudden violence, Paul Thomas Anderson delivers an indie romcom like no other: the story of an angry, mixed-up man-child and a woman with her head in the clouds.

Buy, rent or watch 'Punch-Drunk Love'

Groundhog Day, best romcoms

Groundhog Day (1993)

‘I like to see a man of advancing years throwing caution to the wind. It’s inspiring.’

Bill Murray plays a TV weatherman who’s trapped living the same day every day in this nightmarish fantasy-comedy. He’s forced to re-examine his priorities until he realises he’s in love with his news producer.

Buy, rent or watch 'Groundhog Day'

Harold and Maude, best romcoms
Film, Comedy

Harold and Maude (1971)

‘A lot of people enjoy being dead. But they are not dead, really. They’re just backing away from life. Reach out. Take a chance. Get hurt.’

This cult comedy follows a romantic relationship between a suicide-obsessed teenager and an 80-year-old woman he meets at a funeral. The film's dark humour and daring subject matter still feel taboo.

Buy, rent or watch 'Harold and Maude'

Annie Hall, best romcoms
Film, Comedy

Annie Hall (1977)

‘That sex was the most fun I’ve ever had without laughing.’

From the lobster scenes to Diane Keaton’s waistcoat and tie, this Woody Allen film is referenced so often in popular culture that it’s easy to forget it’s nearly 40 years old.

Buy, rent or watch 'Annie Hall'

When Harry Met Sally, best romcoms

When Harry Met Sally… (1989)

‘I came here tonight because when you realise you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.’

We dare you to try and think of a romcom scene that’s more iconic than Meg Ryan pretending to orgasm in a diner. The tale of two enemies turned friends turned potential lovers asks the question: can guys and girls just be mates?

Buy, rent or watch 'When Harry Met Sally'

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