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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 50 movies, which take a sometimes sweet, sometimes savagely funny look at the pleasures and pitfalls of romance

50

Notting Hill (1999)

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

The world reached peak Hugh Grant with this timeless, soppy but winning tale of a west London bookshop owner who falls in love with an American movie star (Julia Roberts) on a publicity trip.

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49

Much Ado About Nothing (2012)

‘I will swear by it that you love me, and I will make him eat it that says I love not you.’

It’s amazing how close the modern romcom remains to Shakespeare’s sixteenth-century template with its star-crossed lovers, saucy misunderstandings, sarcastic sidekicks and straight-laced parents sticking their noses in. Joss Whedon’s microbudget retelling of the story is sweet, heartfelt and very, very funny.

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48

My Best Friend's Wedding (1997)

‘It’s amazing the clarity that comes with psychotic jealousy.’

Julia Roberts’s ‘other’ smash hit, this may not have attained the iconic status of ‘Pretty Woman’, but it’s much funnier and far less troubling. Pairing up with Cameron Diaz, our Jules plays a young woman who heads to the titular event intent on calling a halt to the proceedings, only to confront her own petty nature.

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47

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).

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46

Muriel’s Wedding (1994)

‘You’re terrible, Muriel.’

As smartly unromantic as a romcom can be and still earn the name, this bittersweet Aussie indie follows the adventures of the ‘undateable’ Muriel Heslop, who flees the small town of Porpoise Spit to the bright lights of Sydney, only to find out that life isn’t quite as upbeat and magical as ABBA made it sound.

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45

While You Were Sleeping (1995)

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

Sure, it’s slushy and old-fashioned, but we’ve got a huge soft spot for this sentimental story of a lonely New Yorker who saves a commuter from being hit by a subway train, only to find herself falling for his nice-guy brother. Sandra Bullock and Bill Pullman are an unexpectedly perfect romantic pairing.

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44

Pride & Prejudice (2005)

‘It is a truth universally acknowledged, that a single man in possession of a good fortune, must be in want of a wife.’

Jane Austen published the story of poor Lizzie Bennet and proud Mr Darcy over 200 years ago, but time cannot wither this happy-ever-after romance – and Joe Wright’s adaptation starring a brilliant Keira Knightley is a keeper.

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43

Sleepless in Seattle (1993)

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

A massive box office hit, this tale of a heartbroken widower who finds the woman of his dreams on the wrong side of the continental divide may lack the pith and wisdom of writer Nora Ephron’s previous film ‘When Harry Met Sally...’ (also on this list), but it remains a smart, boundlessly good-natured comedy.

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42

The 40 Year-Old Virgin (2005)

‘I’m a virgin. I always have been.’

Steve Carell first caused the world to pay attention with this Judd Apatow comedy about a middle-aged loner (Carell) and his small, slow steps towards losing his virginity to a woman (Catherine Keener) who works across the road.

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41

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.

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40

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.

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39

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.

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38

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.

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37

10 Things I Hate About You (1999)

‘Who needs affection when I have blind hatred?’

One of the best high school romcoms, with Heath Ledger as a bad boy in a love-hate relationship with top-of-the-class Julia Stiles, this is an update of Shakespeare’s ‘The Taming of the Shrew’. Still, we don’t think this line is one of the Bard’s: ‘I still maintain he kicked himself in the balls.’

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36

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.

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35

The Princess Bride (1987)

‘This is true love. You think this happens every day?’

Framed as a fairytale told to a sickly boy, this story of bloodthirsty assassins, rampaging pirates, feisty princesses and rhyming giants cleverly punctures its own over-the-top romanticism with slick sarcasm and goofy slapstick.

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34

Shakespeare in Love (1998)

‘You will never age for me, nor fade, nor die.’

Co-written by playwright Tom Stoppard, this winning historical romance imagines a fictional love affair between William Shakespeare (Joseph Fiennes) and an actress (Gwyneth Paltrow) who auditions for the play that Shakespeare is still struggling with – soon to be ‘Romeo and Juliet’.

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33

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’.

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32

Eternal Sunshine of the Spotless Mind (2004)

‘Random thoughts for Valentine’s Day, 2004. Today is a holiday invented by greeting card companies to make people feel like crap.’

You could say that Michel Gondry’s memory-loss comedy is too chilly and cerebral to be truly romantic, but it’s hard to deny the sheer originality of this story of Joel (Jim Carrey) and Clementine (Kate Winslet), former lovers, now estranged, whose memories have been wiped.

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31

Top Hat (1935)

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

If all it had was the glorious ‘Dancing Cheek to Cheek’ sequence, this Fred Astaire and Ginger Rogers musical would already be one of the most swoonsome romances ever shot. But it’s also a witty, heartwarming comedy of aristocratic manners.

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30

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.’

The ’80s nostalgia boom gets into full swing as titular crooner Adam Sandler attempts to steal suburban optimist Drew Barrymore away from her lounge-lizard fiancé. Sandler and Barrymore have attempted to rekindle their flame in two romcoms since, but the results were far from pretty.

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29

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.

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28

But I’m a Cheerleader (1999)

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

The title may suggest yet another infuriatingly perky tale of hunky quarterbacks and pretty prom queens, but this is something far more unconventional. When Megan’s parents send her off to a remote residential camp to cure her latent lesbian tendencies, they don’t really expect her to fall madly in love with the first girl she meets.

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27

Gold Diggers of 1933 (1933)

‘One more look at him with those bedroom eyes and I’ll break your leg!’

It may be remembered for its spectacular Busby Berkeley song ‘n’ dance numbers, but this endlessly enthusiastic backstage comedy all centres around the forbidden passion between a well-bred songwriter and a chippy chorus girl.

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26

Say Anything (1989)

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

Trenchcoated outsider John Cusack is the ultimate teenage romantic hero, hoisting that boombox up on his shoulders and blasting out Peter Gabriel in an effort to win back his preppy sweetheart Ione Skye. The agony of heartbreak was never more acutely captured.

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25

His Girl Friday

‘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?

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24

Four Weddings and a Funeral (1994)

‘Do you think there really are people who can just go up and say, “Hi, babe. Name’s Charles. This is your lucky night”?’

Hugh Grant charmed the world with his turn as the perennial romantic also-ran who attends a series of quintessentially British social occasions – at first even Andie MacDowell seems unable to crack his unlucky-in-love status.

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23

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.

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22

Guys and Dolls (1955)

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

One of the biggest and brashest of the classic MGM musicals, this story of petty crooks on the New York streets blossoms into a heart-stoppingly lovely romance when gambler Marlon Brando whisks his God-bothering paramour Jean Simmons off to Cuba for a little moonlight tête-à-tête.

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21

There’s Something About Mary (1998)

‘I’m fucking with you, Ted!’

It may revel in zip-trapping, dog-electrocuting, cum-in-the-hair grotesquerie, but at its heart this is one of the sweetest romcoms of all, the tale of one man’s journey to get over himself and find true love.

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20

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.

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19

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).

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18

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.

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17

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.

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16

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.

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15

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.

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14

Pretty Woman (1990)

‘I want the fairy tale.’

Okay, so it’s not winning any feminism awards. But it’s futile to resist the charms of ‘Pretty Woman’. Its appeal has a whole lot to do with Julia Roberts – she’s the definition of ‘movie star’, playing the hooker who gets a happy ending.

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13

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.

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12

Manhattan (1979)

‘She’s 17. I’m 42 and she’s 17. I’m older than her father, can you believe that? I’m dating a girl, wherein, I can beat up her father.’

In the late 1970s Woody Allen served up the essential New York movie (and he’s made a few) with this wistful, black-and-white story of a nervy over-thinker (Allen, of course) who steps out with a much younger woman (Mariel Hemingway) before falling in love with a married friend’s secret girlfriend (Diane Keaton).

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11

Clueless (1995)

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

This California-set adaptation of Jane Austen’s ‘Emma’ only really becomes a romcom in its final moments: it’s more interested in privilege, adolescence and a brilliantly sharp observation of high-school manners. But when cupid finally strikes, prepare for one of the most delirious and heartfelt endings in cinema.

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10

It Happened One Night (1934)

‘I’ll stop a car, and I won’t use my thumb!’

The original Hollywood romcom, this whipsmart road movie about an heiress on the run and the sleazy reporter who picks up her trail scandalised America in the 1930s. It went on to win a bunch of Oscars, though, so all was clearly forgiven…

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9

Roman Holiday (1953)

‘It’s always open season on princesses.’

The film that made Audrey Hepburn a star. And she was never better, playing a tomboyish European princess who goes missing from a royal tour of Rome and falls for a tabloid hack.

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8

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.

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7

The Philadelphia Story (1940)

‘We all go haywire at times and if we don’t, maybe we ought to.’

This vinegar-sharp satire about a society dame torn between two equally appealing suitors is steeped in Old-Hollywood elegance and fiery, proto feminist irony. Katharine Hepburn was never more bullishly brilliant.

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6

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.

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5

Groundhog Day (1993)

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

This deeply insightful tale of a man forced to live the same day over and over balances existential inquiry with bitterly funny, spiky comedy. But the ultimate message is that love conquers all, as long as you’re willing to open yourself up to it.

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4

A Matter of Life and Death (1946)

‘I love you, June. You’re life and I’m leaving you.’

Michael Powell and Emeric Pressburger’s dizzying wartime fantasy has more on its mind than simply love and humour – as the title suggests, it covers pretty much the entire spectrum of human experience, and beyond. But at its heart, this is a giddily funny romance.

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3

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 quirky hippie romance was forgotten for years. Now thanks to famous fans like Wes Anderson, it’s become a cult classic. In this unconventional love story, depressed 20-year-old Harold meets fun-loving 79-year-old eccentric Maude at a funeral they’re both gatecrashing.

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2

Annie Hall (1977)

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

Two years after their real-life split, Woody Allen and Diane Keaton made one of the best romcoms of all time. Kooky scatterbrain Keaton is the perfect girl for neurotic comedian Woody. So why does their relationship end?

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1

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.’

The perfect script, the perfect couple, the perfect setting… The perfect romcom. With more laser-sharp insight into relationships than a decade’s worth of agony aunt columns, ‘When Harry Met Sally…’ wryly skewers the pitfalls of dating while still celebrating the eternal pull of romance.

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