David Farnor | On 24, May 2020

The romantic comedy is one of cinema’s most under-appreciated genres, with films dismissed as guilty pleasures or, worse, “chick flicks”. It doesn’t help that the genre can also be highly inconsistent, with movies of all quality levels released over the years. But along with the screwball gems of the 1930s, 1940s and 1950s, there’s an undeniable peak that dates back to the 1980s and 1990s, when the genre was at its most prolific and profound – and its most formative, even though its influence was limited to a perspective that was largely white, heterosexual and middle-class. As the genre continues to widen its perspectives and subvert tropes, we look back at the rom-com’s most definitive era – pre-2000 – to round up the ones to fall in love with all over again.

These, in no particular order, are the best classic romantic comedies:

The Apartment

Billy Wilder gave us one of the all-time great rom-coms in Some Like It Hot, and it’s testament to this other classic’s brilliance that it’s hard to know whether it even counts as a romantic comedy, as it takes us into the world of workplace romance, cruel capitalism, transactional relationships and – whisper it – infidelity.

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Bringing Up Baby

Cary Grant and Katharine Hepburn are a joy to watch in this laugh-out-loud romantic farce.

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The African Queen

After the death of her brother, Rose Sayer must flee German East Africa and finds the only safe conveyance left: a dilapidated river steamboat. The ship is run by the grumpy and usually drunk Charlie, who goes toe to toe with the imperious, straight-laced Rose throughout their perilous journey. Humphrey Bogart and Katherine Hepburn star in John Huston’s odd couple classic.

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His Girl Friday

Howard Hawks delivered one of the best examples of Hollywood’s early screwball capers with this hugely entertaining romp about a newspaper reporter and the editor of the rag – an excuse for lightning-fast banter between Cary Grant and Rosalind Russell.

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Harold and Maude

Hal Ashby’s 1971 romantic comedy telling the twisted story of a suicidal young man and the older woman he meets while attending a funeral – a hobby that they both share. The least likely start to a rom-com ever? Harold and Maude is as dark as it is sentimental, and we wouldn’t have it any other way.

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Charade

“You know what’s wrong with you?” “No, what?” “Nothing.” That’s the sound of Audrey Hepburn and Cary Grant colliding in Charade, and the result is as enjoyably glamorous as cinema gets. The 1963 flick sees Hepburn play Regina Lampert, whose husband, Charles, is murdered in Paris, causing a bunch of sinister men to descend, looking for the thousands of dollars he left behind. Also on the scene is Peter Joshua (Grant), who may or may not be one of the good guys. The result is an iconic screen duo that nail the 60s romantic caper that kept rom-coms bringing in audiences for a decade.

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To Catch a Thief

When a reformed jewel thief is suspected of returning to his former occupation, he must ferret out the real thief in order to prove his innocence. Alfred Hitchcock. Gracy Kelly. Cary Grant. What more could you want?

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Pretty Woman

When millionaire Edward enters into a business contract with Hollywood sex worker Vivian, he loses his heart in the bargain. Cheesy? Yes. Romantic? That too, less because of its dubious update of Pygmalion and more because of the star-powered chemistry between Richard Gere and Julia Roberts.

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Moonstruck

Cher and Nic Cage are together at last in this romantic comedy about Loretta Castorini, a bookkeeper from Brooklyn, New York, who finds herself in a difficult situation when she falls for the brother of the man she has agreed to marry.

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Clueless

Alicia Silverstone is timeless in this witty high school update of Jane Austen’s definitive rom-com, Emma.

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Watch on Netflix UK (£8.99 a month)

Groundhog Day

Harold Ramis’ comedy about a weatherman who finds himself reliving the same day over and over again is funny, sweet, profound and features a superb central turn from Bill Murray. A verifiable classic – and ideal for convincing someone who doesn’t like romantic comedies that, actually, they do.

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The Graduate

Mike Nichols’ seminal coming-of-age tale, starring Dustin Hoffman and Anne Bancroft, still inspires new generations of lost college-leavers today, a sign of just how timeless his knack for entertaining people was – and continues to be. The film dares to explore the notion of a relationship between an older woman and a young man, but – even bolder – questions the very idea of a happy-ever-after, as our naive lead couple begin to understand the weight of commitment that a relationship entails.

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Breakfast At Tiffany’s

A young New York socialite takes interest in a man who moves into her apartment building downstairs in this lovely adaptation of Truman Capote’s novel. Audrey Hepburn is a delight.

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You’ve Got Mail

Nora Ephron’s final definitive rom-com once again brings together Tom Hanks and Meg Ryan to tell the tale of a small bookshop owner who finds herself in competition with the boss of a gigantic chain of stores – all while the two fall in love online. A nice, forward-thinking story of modern technology and offline identity, it paved the way for the rom-com to enter the modern age. It’s testament to how good Hanks and Ryan are on-screen together that you just about forgive him for some gaslighting behaviour in the movie’s final act.

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While You Were Sleeping

The archetypal example of a romantic comedy that hinges on one person doing something highly questionable – only to be forgiven by everyone in the audience because their obsessive feelings for another person are eventually reciprocated. Jon Turteltaub’s 1995 gem sees Sandra Bullock step into a leading role as a Chicago everywoman who is mistaken for being engaged to a guy she fancies on the train (Peter Gallagher). After saving his life, he winds up in a coma – and his family immediately invite her into the fold. Enter the guy’s charming, suave and suspicious older brother (Bill Pullman)…

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Much Ado About Nothing

The will-they-won’t-they, do-they-don’t-they formula of bickering opposites that ultimately attract began, arguably, with Shakespeare’s Much Ado About Nothing, and there’s no better adaptation than Ken Branagh’s 1993 charmer, which has a stellar cast including Emma Thompson, Kate Beckinsale and Keanu Reeves.

Not available on UK VOD.

10 Things I Hate About You

10 Things I Hate About You won over hordes of teenagers with its wry realisation that The Taming of the Shrew’s gender politics and inequality are issues dealt with every day in high school. Not only a memorable Shakespeare adaptation but also a definitive high school movie in its own right, Gil Junger’s knowing update has enough laughs to keep you entertained, even without the original dialogue – and, thanks to a standout sequence involving a marching band, gave the world a chance to fall in love with Heath Ledger’s singing voice. All together now: “I love you, baby, and if it’s quite alright, I need you, baby…”

Watch on Disney+ (£5.99 a month)

Notting Hill

Hot on the heels of Four Weddings and a Funeral, Hugh Grant and Richard Curtis reunite for this second tale of a nervous Brit falling for a wealthy American women – and, while this is an undoubted white, privileged world, there’s an extra note of authenticity to Julia Roberts’ portrayal of a famous movie star, while Rhys Ifans’ scene-stealing best friend would set the template for comic relief sidekicks for many rom-coms to come.

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Watch on Netflix UK (£8.99 a month)

Sleepless in Seattle

Nobody does it quite like Nora Ephron, and this 1993 gem confirms it, as she brings together Tom Hanks and Meg Ryan to play a widower who finds a second change at love through a radio show. It’s an endearingly sensitive rom-com, and one that established a screen partnership that would become one of the most bankable and loveable double-acts in Hollywood history.

Watch on Sky Cinema and NOW (£11.99 a month)

My Best Friend’s Wedding

“Michael’s chasing Kimmy. You’re chasing Michael. Who’s chasing you?” That’s the catty observation made by George (Rupert Everett) partway through My Best Friend’s Wedding, and it’s one that gets right to the heart of what makes this romantic comedy one of the genre’s best: it not only suggests that, just maybe, Julianne (Julia Roberts) might not be destined to marry the man she thinks is The One, but also reminds us that sometimes, the real love in our lives are the friends to help us realise the awkward truths.

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Four Weddings and a Funeral

“Is it still raining? … I hadn’t noticed.” Richard Curtis’ portrait of 30-somethings trying to find their way through love is a wonderfully funny and adorably earnest affair. Hugh Grant gives himself an iconic type as Charles, a good-natured bumbling Brit who tries to connect with elusive American Carrie over several weddings and a funeral. From the swear-filled rush to get ready to the decision to include death as well as (multiple) nuptials, this is an impressively messy ensemble piece that, despite hitting peak Curtis levels, remains a formative experience for anyone who’s seen it.

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It Happened One Night

Frank Capra’s 1934 flick, which sees a spoiled heiress (Claudette Colbert) flee her controlling father, only to wind up stuck with a cynical newspaper reporter (Clark Gable). Their odd couple exchanges were not only laugh-out-loud funny and endearingly sweet, but also went on to define the romantic comedy – leaving the audience longing for the lead couple to get together in an era where on-screen passion was prohibited.

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Some Like It Hot

When two musicians accidentally witness the St. Valentine’s Day Massacre, they get out of town the only way they know how – dressed as women. The result is dated in many ways, but remains the definitive Marilyn Monroe performance, cementing her irresistible screen presence with a clumsy charm and note-perfect comic timing. Never seen Billy Wilder’s comedy classic? Well, nobody’s perfect.

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When Harry Met Sally

Can a man and woman ever be just friends? That’s the age-old question posed by When Harry Met Sally, which has become the definitive romantic comedy – the kind of witty, moving film that other romantic comedies dream of being. That’s partly because of how funny it is, but it’s also because of how honest it is, with Nora Ephron’s remarkable script coming from a place of truth, and Billy Crystal and Meg Ryan (her again) proving a perfect piece of casting that rings with authentic friendship as well as buzzes with romantic tension. In a cute flourish, director Rob Reiner intercuts the movie with vox pops of elderly people recounting their relationships, based on true stories, which only underlines how convincing the whole endeavour is. And, of course, there’s That Sandwich Scene.

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In & Out

Frank Oz’s delightful rom-com is one of the rare attempts by mainstream Hollywood to explore homosexuality within the confines of the romantic comedy – and who better to bring audiences along for the ride than the ever-charming Kevin Kline, who plays a teacher trying to prove he’s straight after a student outs him.

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There’s Something About Mary

Amid the Farrelly Brothers varied back catalogue is this gross-out rom-com that might not be perfect, but undeniably set the template for modern rom-coms to follow in its wake, as Ben Stiller plays a geek trying to track down his high school sweetheart (Cameron Diaz), who seems to win the heart of every man she meets.

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