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"The 40-Year-Old Virgin"

The best romantic comedies of all time

Love is a funny old game. Or at least it is in the 70 best romantic comedies in cinema history.

Written by
Cath Clarke
&
Phil de Semlyen
Written by
Andy Kryza
&
Matthew Singer
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Love hurts, love scars. But love is also really, really funny. If you’ve ever found yourself in its grip, then you know the strange ways it can make you feel, and the weird things it’ll make you do. And even if you haven’t, well, there’s a whole genre dedicated to letting you know how funny it can be. Romantic comedies have often been dismissed as ‘chick flicks’, but the best of them reflect emotional truths everyone can relate to on one level or another. 

No wonder the romcom persists as one of the most broadly accessible genres in all of film. But just as not all love stories are the same, neither are romantic comedies. Some are farcical, others more sophisticated, some cynical, others straight-up silly. Love contains multitudes, and so do romantic comedies, and we considered it all when putting together this list of the best romcoms of all time.

Written by Dave Calhoun, Cath Clarke, Tom Huddleston, Kate Lloyd, Andy Kryza, Phil de Semlyen, Alim Kheraj & Matthew Singer

Recommended:

😍 The 100 best romantic films of all-time
🤣 The 100 best comedy movies
😳 The 101 best sex scenes of all time
🔥 The 100 best movies of all-time

The best romantic comedies of all time

  • Film
  • Comedy

‘Bridget Jones, wanton sex goddess, with a very bad man between her thighs…’

Based on Helen Fielding’s newspaper-column-turned-bestselling-book about a loveable but perpetually single thirtysomething living in London, Bridget Jones’s Diary is very much a product of its time (hopefully today, we wouldn’t dare consider Bridget overweight or the fact that she’s single in her thirties a problem). That being said, it remains a charming and deeply relatable film, thanks mostly to double-Oscar-winner Renée Zellweger, who injects a lovable charm into her portrayal of the almost perennially unlucky-in-love Bridget. Zellweger’s performance – British accent and all – is just highly believable; her Bridget is one of us (although how an assistant at a publishing house can afford to live alone in a one-bedroom flat in London Bridge requires a little suspension of disbelief). Throw in Hugh Grant as a smarmy love-rat, Colin Firth as a bumbling gentleman and a script co-written by Richard Curtis, and you’ve got romcom royalty.

My Best Friend’s Wedding (1997)
  • Film
  • Comedy

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

Julia Roberts’ career-focused food critic is the perfect foil for bubbly law student Cameron Diaz in this love triangle romance. The real highlight is Rupert Everett, though, who plays Julia’s trouble-making gay best friend with devilish flair.

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Boomerang (1992)
Paramount

68. Boomerang (1992)

‘Hey, you’re not getting serious on me, are you?’

In which Eddie Murphy essentially plays a 1990s version of Don Draper, an ad executive and serial womaniser, who finally meets his match in his new boss, portrayed by Robin Givens. Critics didn’t quite know what to make of sex comedy set in the corporate world and with a primarily Black cast, but it confirmed Murphy as a viable romantic lead, and time has shown that it’s better than the initial reviews - and it’s got a killer soundtrack.

It’s Complicated (2009)
  • Film
  • Comedy

‘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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Muriel’s Wedding (1994)
  • Film
  • Comedy

‘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.

  • Film
  • Comedy

‘All men are islands.’

Plug Hugh Grant into basically any romantic comedy back in the ’90s and early 2000s and you’re going to a get a film that’s watchable at the very least, but this Nick Hornby adaptation pushes the limits of his ‘irresistible cad’ persona… and it still ends up a stone-cold charmer. Grant plays Will Freeman, a layabout playboy who has no compunction lying about being a single dad if it will help him get laid. Then, of course, he gets mixed up with a fatherless tween (Nicholas Hoult) and an actual single mother (Rachel Weisz) who melt his defences and push him – kicking and muttering and awkwardly strumming a guitar at a school talent show – toward maturity.

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Palm Springs (2020)
Photograph: Jessica Perez, Hulu

64. Palm Springs (2020)

‘One time, I smoked a bunch of crystal, and made it all the way to Equatorial Guinea. It was a huge waste of time.’

A new addition to the romcom canon but a worthy one, this
Groundhog Day-ish comedy ticks all the boxes. It’s funny, sharply written, and, by the end, offers a genuinely soulful examination of the mysteries of human connection. Andy Samberg is a wedding guest permanently stuck in a one-day time loop and Cristin Milioti is the fellow he accidentally lures into his own personal Palm Springs purgatory. They hate each other, then they don’t, then they do again, then JK Simmons’s coked-up lunatic turns up with a bow and arrow. 

While You Were Sleeping (1995)
  • Film
  • Comedy

‘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. 

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  • Film
  • Comedy

‘You think that the world revolves around Gary Valentine and whatever stupid shit you come up with’.

Paul Thomas Anderson’s meandering ode to 1970s LA is framed around the connection between a loquacious teenager (Cooper Hoffman) and a floundering woman (Alana Haim) ten years his senior. Some wrung their hands over the age difference, while even those involved tried to argue that their relationship is more of a meaningful friendship than a romance, but there’s no denying the sheer joy the two characters bring to every scene they share, even when they’re trying to hurt each other. 

  • Film
  • Comedy

‘You know, when you grab a woman’s breast… and you feel it, and… it feels like a bag of sand.’

It would have been easy to make a movie called The 40-Year-Old Virgin that outright mocks its protagonist, and that’s probably what would have happened if it was made by, say, the Farrelly brothers. But Judd Apatow mines the humour of middle-age sexual inexperience without being mean about it. Most of the credit, though, goes to Steve Carrell for making unlucky-in-lust electronics salesman sympathetic rather than merely pathetic. When he finally forges a connection with single mum Catherine Keener, it might be predictable, but it’s never cloying or insincere.   

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Roxanne (1987)
  • Film
  • Comedy

‘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.

Always Be My Maybe (2019)
Photograph: Netflix

59. Always Be My Maybe (2019)

‘Do you have any dishes that play with the concept of time?’

The centerpiece Keanu Reeves cameo made headlines – how could it not? – but Always Be My Maybe is so much more than Neo’s metaphysical restaurant questions. At its heart – and it’s a huge heart – the story of two childhood friends resisting their lifelong chemistry after reuniting as adults is pure romcom gold in the mold of When Harry Met Sally. Keanu may have the wattage, but stars Randall Park and Ali Wong are truly unforgettable as they struggle to break out of the friend zone. 

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  • Film

‘Honey, all you have to be by the time you’re 23 is yourself.’

The ultimate Gen X time capsule, Reality Bites presents Winona Ryder’s aspiring documentarian with an extremely of-its-time romantic dilemma: does she date the uncool yuppie who respects her (Ben Stiller) or the hot, aloof slacker (Ethan Hawke) who treats her like crap? Trust us, in the ’90s, this was a real Sophie’s Choice. Audiences have been debating her decision ever since.

Forgetting Sarah Marshall (2008)
  • Film
  • Comedy

‘When life hands you lemons, just say, “Fuck the lemons,” and bail.’

Judd Apatow got credited with ‘reinventing’ the romcom in the mid-aughts, so it’s a bit ironic that the Apatow-related vehicle that’s aged the best is the most orthodox-feeling. (Apatow produced, while Nicholas Stoller directed.) Jason Segel plays a lovable schlub who blows his improbable relationship with a hot TV star (Kristen Bell), only to half-accidentally woo the hot concierge (Mila Kunis) at the Hawaiian resort he retreats to post-breakup. So it’s not exactly believable, but it succeeds because of the perfect casting - Russell Brand, in particular, is so good as Segel’s dipshit cock-rocker foil he got his own spinoff, the underrated Get Him to the Greek - and because the screenplay, written by Segel, balances warmth and raunch more deftly than any other comedy of the era.

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  • Film
  • Comedy

‘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.

  • Film

‘Is French kissing in France just called kissing?’

This 1995 Lawrence Kasdan caper earns its spot here just by dint of Meg Ryan and Kevin Kline’s spiky-sparky double act. She’s a ditzy teacher with a cheating fiancé; he’s a French thief. The pair of them are… well, you can probably guess. There are enough ideas to see the functional plot through, such as when Ryan’s aereophobic Kate is addressed by the disembodied safety briefing voice on her flight (‘Tell me Kate, what are you thinking about?’). But it’s the culture-clash chemistry between ignorant American and rude Gaul, played delightfully by two actors clearly having a ball, that makes it sing. The glorious Parisian and Riviera locations don’t hurt either.

Something Wild (1986)
  • Film

‘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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Jamón, Jamón (1992)
  • Film

‘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.

Love, Simon (2018)
  • Film
  • Drama

‘I'm straight. I’m sorry, mom, it’s true.’ 

Bearing the heart and wit of classic John Hughes, this modern teen comedy focuses on Simon Spier, a closeted high schooler whose life is thrown into turmoil when a classmate intercepts emails sent to a fellow gay student and blackmails him. It’s the first queer coming-of-age romance released by a major studio, and inspired a spinoff TV series.

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Heartbeats (2010)
  • Film
  • Drama

‘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.

10 Things I Hate About You (1999)
  • Film
  • Comedy

‘Who needs affection when I have blind hatred?’

For some, Heath Ledger’s signature cinematic moment isn’t the ‘pencil trick’ scene from The Dark Knight but the time he serenaded Julia Stiles with ‘Can’t Take My Eyes Off You’ from the bleachers in this teen-movie take on Taming of the Shrew. Indeed, it’s the highlight of this classic ‘90s flick, where Ledger plays the bad-boy high schooler who takes on the job of trying to woo Stiles’s  seemingly unwooable and prickly overachiever. But the whole thing is a delight. 

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Gregory’s Girl (1981)
  • Film

‘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.

  • Film

'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.

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  • Film
  • Animation

‘Eeeeeeee-va.’

Pixar’s grandest artistic triumph is a poignant environmentalist parable, but at its core, it’s basically a love story. Granted, it’s about the love between a sentient trash compactor and a giggly, egg-shaped droid, and their only shared dialogue is repeating each other’s names, but they have more natural chemistry than you’ll find in the entire Hallmark Channel filmography. It’s the greatest silent romance since Chaplin and the flower girl.

  • Film
  • Comedy

‘Honestly, this has been like the best few weeks of my entire life.’

The optics of a driven female politician needing to become more likeable to make it to the White House feel a little 2016. But don’t let that put you off this unlikely but sparky pairing of Charlize Theron as the wannabe Potus and Seth Rogen as the schlebby, liberal-minded journo she hires to make her speeches more relatable and finds herself falling for. There’s even a faint screwball edge to their courtship, as the pair take in overseas revolutions, political rallies and one majorly funny MDMA binge.

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  • Film
  • Comedy

‘I had to go to Greek school, where I learned valuable lessons such as, "If Nick has one goat and Maria has nine, how soon will they marry”’?

It’s hard to believe this humble indie comedy is still the highest grossing romcom of all-time – that is, until you actually watch it, and see what an easy pleasure it is. Written by and starring then-complete-unknown Nia Vardalos, its story is familiar: a modest Greek-American woman wants to marry the non-Greek man of her dreams (John Corbett), upsetting her traditionalist father. But the movie is full of such wonderfully observed details about first generation immigrant families – and all families, really – that it’s easy to understand how word-of-mouth gradually blew it up into a massive hit. 

  • Film
  • Family and kids

As you wish...

Fairy tales have never, ever been funnier than this swashbuckling romance. It boasts an undercard packed with so much god-level comic talent (cameo honours are a toss-up between Peter Cook as the Impressive Clergyman and Billy Crystal as Miracle Max) that it can even afford to have Christopher Guest playing the mirthless baddie. Headliners Cary Elwes and Robin Wright provide the magic as lovebirds for the ages, Westley and Buttercup.

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Top Hat (1935)
  • Film
  • Drama

‘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.

Eternal Sunshine of the Spotless Mind (2004)
  • Film

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

It’s rare to find a film that traverses the comedy, psychological thriller, romance and sci-fi genres as easily as Eternal Sunshine. Jim Carrey and Kate Winslet play exes who ask scientists to erase their memories of each other.

The Wedding Singer (1998)
  • Film

‘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.’

It wasn’t until Punch Drunk Love that critics started taking Adam Sandler seriously as an actor, but The Wedding Singer proved he could at least play something other than a screeching man-child – in this case, a bemulleted ’80s rock frontman hopelessly in love with an already betrothed Drew Barrymore. It’s a simple premise executed with a genuine sweetness few at the time thought Sandler had in him.

  • Film

‘If basketball is all you care about, why you bonin' me? Why don't you bone Dick Vital?’

Love & Basketball is slotted as a ‘romantic drama’ more often than a comedy, but that’s mostly because the movie’s humour doesn’t feel the least bit contrived. Instead, it’s funny in the way real life is, and how real people are when they’ve known each other forever. Sanaa Lathan and Omar Epps play childhood friends and on-again, off-again romantic partners united by a love of basketball, whose individual hoop dreams keep them weaving in and out of each other’s lives. Writer-director Gina Prince-Bythewood has said her goal was to write ‘a Black When Harry Met Sally’, and she didn’t land too far off.

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  • Film

‘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 RuPaul. 

Gold Diggers of 1933 (1933)
  • Film
  • Drama

‘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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  • Film
  • Fantasy

‘It’s better to help people than a garden gnome’.

A truly magical film, Jean-Pierre Jeunet’s visionary, if sometimes overly cutesy romantic fantasy made the world fall in love with Audrey Tautou. She plays the titular whimsical Parisian waitress who endeavours to improve the lives of those around her, while putting her own happiness on the backburner – that is, until an eccentric artist named Nino enters her life.

Say Anything (1989)
  • Film

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

Every great 1980s teen movie not made by John Hughes is inevitably going to get compared to John Hughes. But Say Anything… is much closer to more ‘adult’ romcoms like Annie Hall and The Graduate than it is to Sixteen Candles. It’s a testament to how much respect freshman writer-director Cameron Crowe shows the seemingly mismatched couple at the film’s centre, mega-charming slacker Lloyd Dobler (John Cusack) and underconfident overachiever Diane Court (Ione Skye). Neither is a straightforward archetype, and by the end, their relationship makes complete sense. Make no mistake, though: this is still a teen movie. After all, standing on someone’s lawn with a boombox blasting Peter Gabriel is exactly the kind of embarrassingly romantic gesture only a teenager could come up with.

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His Girl Friday (1940)
  • Film
  • Comedy

‘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?

Four Weddings and a Funeral (1994)
  • Film
  • Comedy

'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.

 

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Barefoot in the Park (1967)
Photograph: British Film Institute

33. Barefoot in the Park (1967)

Marital discord is the theme of this screen adaptation of the Neil Simon play, but this ain’t The War of the Roses. Instead, it’s a romantic farce so light it seems to float on air. Jane Fonda and Robert Redford are a newlywed couple who, other than being outrageously attractive, seem to be a bit mismatched: he’s buttoned-up and career obsessed, she’s carefree enough to run through Washington Square Park without shoes on. Moving into a fifth-floor apartment in Greenwich Village exacerbates issues they’d previously covered up with passionate lovemaking. At no point does it feel like their relationship is in true jeopardy, but that hardly dilutes the movie’s bubbly charm, nor the chemistry of its two leads.   

The Apartment (1960)
  • Film
  • Comedy

‘Shut up and deal.’

Sad, cynical and fairly dark for its day, Billy Wilder’s tinted-black comedy is nonetheless timelessly funny and ultimately endearing, qualities owing to the respective strengths of its two leads. Jack Lemmon is CC Baxter, a white-collar pushover lending out his flat to the higher-ups at his office so they can carry out their extramarital trysts in exchange for a promotion kept just out of his reach. Then the cute office elevator girl (Shirley MacLaine) shows up there with his slimebag boss (Fred MacMurray) and the whole arrangement begins to crumble – cookie-wise. 

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Guys and Dolls (1955)
  • Film
  • Drama

‘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. 

  • Film

‘See me, I’m kinda into ugly. But only if it’s sexy ugly’.

This small-time indie comedy turned heads in the early 2000s by suggesting that sexual fluidity might just be totally normal. Two straight strangers (Jennifer Westfeldt and Heather Juergensen) bond over their dissatisfying experiences dating men, and figure the obvious solution would be to date each other. If made today, the story’s ultimate resolution would likely play out a bit differently, but romcoms with queer themes are still rare two decades later, so Kissing Jessica Stein deserves commendation for tackling the subject at all.

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  • Film
  • Comedy

‘Tomorrow the birds will sing’.

Maybe Charlie Chaplin’s most enduring film, City Lights finds the comedy legend assuming the role of the Little Tramp once more, falling in love with a blind flower girl who, through a series of misunderstandings, comes to believe that he’s a millionaire. Released as a silent picture three years into the talkie era, it continues to enrapture cinema lovers generations later.  

  • Film
  • Comedy

‘Your heart attack could be the best thing that ever happened to me’.

Nancy Meyers, master of the populist romcom, brings her light, frothy touch to this romp about a senior playboy (Jack Nicholson) slowly falling for – gasp! – a woman his own age (Diane Keaton). In typical Meyers fashion, it swerves toward corniness at times, but always gets pulled back from the brink by the smart script and delightful performances at its centre.

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There’s Something About Mary (1998)
  • Film
  • Comedy

‘I’m fucking with you, Ted!’

If it was just a movie about a woman unwittingly putting splooge in her hair, well, we’d probably still laugh uproariously despite our better judgment, but it certainly wouldn’t make this list. What makes the Farrelly brothers’ third feature a classic romcom is that it manages to balance the duo’s signature gross-out gags with true heart, to a degree few ‘dumb’ comedies ever achieve. Indeed, there’s just something about the combination of Cameron Diaz – the mega It Girl of the era – and Ben Stiller as her hapless high school paramour that makes it work, frank-and-beans jokes and all. 

  • Film
  • Comedy

‘There is a very fine line between love and nausea.’

Coming to America is best remembered for Eddie Murphy’s showstopping multi-character performance. Too bad it’s not also lauded as the perfect romcom that it is. If it were, perhaps Eddie’s ‘90s output would have had fewer Klumps and more turns like his charming African prince seeking his future queen in, of course, Queens. Murphy is at his charming best as the smiling paragon of innocence, and his chemistry with Shari Headley is as touching as the fish-out-of-water comedy is hilarious.

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Scott Pilgrim vs the World (2010)
  • Film
  • Action and adventure

‘I kind of feel like I'm on drugs when I'm with you. Not that I do drugs. Unless you do drugs. Then I do drugs all the time, every drug’.

There are comic-book movies and then there are movies that truly feel like live-action comic books. Edgar Wright’s fluorescent, hyperactive adaptation of the Scott Pilgrim graphic novel series is maybe the best-ever example of the latter. In most scenarios, Michael Cera might not be the first choice to portray a superhero, but he’s the perfect choice to play the titular protagonist here, a nerdy Canadian indie rocker forced to go to war with the villainous ex-boyfriends of his neon-haired paramour (Mary Elizabeth Winstead). Romance doesn’t get more kinetic.

The Lady Eve (1941)
  • Film
  • Comedy

‘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.

She's Gotta Have It (1986)
  • Film
  • Comedy

‘Nola’s about as dependable as a ripped diaphragm’.

Spike Lee’s breakthrough feature was a watershed moment for independent film, the onscreen portrayal of African-Americans and the presentation of female sexuality in film. In a reversal of most onscreen romantic entanglements, it’s the woman – a young Brooklyn graphic artist named Nola Darling (Tracy Camilla Johns) – enjoying a series of casual sexual relationships, and her three male suitors are the ones desperate to convince her to commit.   

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  • Film
  • Comedy

‘Snap out of it!’

Cher gives an Oscar-winning performance in Norman Jewison’s film about a 37-year-old widow who falls in love with her fiancé’s young hot-headed brother, played by a wounded and grunting Nicolas Cage. Not only does the film never mention the age gap between the two romantic leads, but Jewison is loose-handed with genre, adding sprinkles of magical realism to what is otherwise a kitchen-sink comedy about two New Yorkers who fall in love. It’s wickedly funny and romantic as hell.

Bull Durham (1988)
  • Film
  • Comedy

‘The world is made for people who aren’t cursed with self-awareness.’

Former minor leaguer turned director and screenwriter Ron Shelton hit a home run with this sports dramedy about a love triangle – or should that be triple play? – involving two members of a low-level baseball club named Crash Davis (Kevin Costner) and Nuke LaLoosh (Tim Robbins) competing for the affections of team groupie Annie Savoy (Susan Sarandon). It earned Shelton an Oscar nomination for Best Original Screenplay, which it should have won simply for the character names alone. Seriously, there’s also a player named Meat.

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I Know Where I’m Going! (1947)
  • Film

‘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 (1955)
  • Film
  • Comedy

‘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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The Shop Around the Corner (1940)
  • Film

‘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.

Bringing Up Baby (1938)
  • Film

‘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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  • Film
  • Comedy

Melanie Griffith’s breakout in Mike Nichols’ fizzy corporate comedy is still the role she’s most associated with, and with good reason. She’s an all-time charmer as Tess McGill, a secretary at a brokerage firm who, using her cunning, her deceptively bubbly demeanour and a bit of deception, works her way up the corporate ladder - and into the arms of Harrison Ford, her boyishly handsome coworker.

Pretty Woman (1990)
  • Film
  • Comedy

‘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.

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Ninotchka (1939)
  • Film
  • Comedy

‘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.

The Big Sick (2017)
  • Film
  • Comedy

'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.

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Clueless (1995)
  • Film
  • Comedy

‘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.

It Happened One Night (1934)
  • Film
  • Comedy

‘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…

Roman Holiday (1953)
  • Film
  • Romance

‘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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Show Me Love (1998)
  • Film

‘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.

  • Film

‘What can you do with your life if all you can do is look good?’

Among the smartest and most ‘adult’ of all romcoms, writer-director James L Brooks satirises the Me Decade and the TV news biz while also telling a deeply relatable story about love and careerism. Albert Brooks is a talented – if not precisely telegenic – journalist competing for the affections of his work-obsessed colleague (Holly Hunter) with a newly hired himbo, played by William Hurt. Jack Nicholson also shows up in an unbilled role as the national anchor whose job Brooks covets.  

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The Philadelphia Story (1940)
  • Film
  • Comedy

‘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.

Punch-Drunk Love (2002)
  • Film
  • Comedy

‘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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Groundhog Day (1993)
  • Film

‘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.

  • Film

‘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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Harold and Maude (1971)
  • Film
  • Comedy

‘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.

Annie Hall (1977)
  • Film
  • Comedy

‘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 45 years old.

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When Harry Met Sally… (1989)
  • Film

‘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?

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