The 34 greatest romantic comedies, from Pretty Woman to The Philadelphia Story

Filled with weddings, sardonic best friends and an abundance of Julia Roberts, these are the greatest romantic comedies of all time – ranked by Adam White from 34 to 1

Thursday 17 August 2023 06:58 BST
Beautiful people falling in love: Poster artwork from Pretty Woman, Bridget Jones's Diary, Brown Sugar, The Philadelphia Story, There's Something About Mary and When Harry Met Sally
Beautiful people falling in love: Poster artwork from Pretty Woman, Bridget Jones's Diary, Brown Sugar, The Philadelphia Story, There's Something About Mary and When Harry Met Sally (Disney/Universal/Fox/Columbia)

The metaphorical birthplace of Julia Roberts, Meg Ryan and tubs of ice cream eaten sadly on the sofa, the romantic comedy has survived cliche, shifting cultural mores and Kate Hudson and remains one of the most important and emotionally essential film genres in existence. And that’s despite almost all of them being exactly the same. But we love them anyway, regardless of whether they’re secretly awful or genuinely brilliant.

To compile the genre’s 34 best, it was important to maintain a strict criteria: a romantic comedy must build to a final rush of feeling and close on a kiss; the central romance must be the primary hook for the entire film, and the usual rules of good filmmaking don’t necessarily need to apply when it comes to films designed to make you feel giddy inside. Because, truthfully, we’re just a bunch of lovesick romantics, standing in front of a television set, asking to watch beautiful people fall in love. Did your favourite make the list?

34. Crazy Rich Asians (2018)

Crazy Rich Asians may not have saved the romantic comedy in 2018, as everyone predicted it would, but it remains a breathless celebration of the genre – with a far-too-late-in-the-day but still wholly appreciated diversity at its centre. Constance Wu is the New York economics professor who discovers her apparently average Joe fiancee is in fact Singapore royalty. What follows is a fish-out-of-water comedy that both indulges in its gorgeous opulence while never becoming too in awe of it. Michelle Yeoh is a standout, as a high society matriarch intimidatingly protective of her son.

33. I Like It Like That (1994)

The first US studio movie to be directed by a black American woman, the great Darnell Martin, I Like It Like That sports the colour and sweatiness of a humid day in August. Lauren Velez is a Bronx spitfire forced to raise money fast when her sexually voracious husband is thrown in jail. The film’s energy never lets up as the pair squabble over infidelity and low-key acts of revenge, while Martin captures the Puerto Rican boroughs of New York like a never-ending pop video, full of noise, laughter and steam rising elegantly from manhole covers.

32. Long Shot (2019)

Released a decade after Knocked Up, Seth Rogen’s adorable if occasionally bro-heavy first stab at the romcom, Long Shot bears the fruits of a man who has fixed some of his more regressive tendencies in the interim, producing something smarter, more sensitive and as interested in the feelings, neuroses and dialogue of his female co-star as he is to himself. He is a left-wing journalist recruited as a speechwriter for his former babysitter (Charlize Theron), who is now the US secretary of state, and the pair forge an unshakable bond despite their wildly juxtaposed looks and vocations in life. Against the odds, Theron and Rogen are adorable together, while the film strikes a wonderful balance between sweetness and crudity. Long Shot may have flopped at the box office, but it’s the closest thing we’ve had to a romcom classic in years.

31. I Give It a Year (2013)

I Give It a Year is a perfect example of an anti-romcom that doesn’t lord superiority over its more earnest counterparts. Rafe Spall and Rose Byrne are a Richard Curtis-ian couple who desperately need to break up, while both circling other people (Anna Faris and Simon Baker) they’re better suited for. With Stephen Merchant and Minnie Driver bagging all the best lines as wacky sidekicks to our heroes, the film feels like the last of a dying breed – witty, naughty and incredibly British in its comic sensibility.

30. Pretty Woman (1990)

Pretty Woman certainly isn’t good, with an undercurrent of sleaze so disquieting that it’s no real surprise to learn it was once planned to be a gritty sex work drama that ended in tragedy. But Julia Roberts is pure star-is-born loveliness here, beloved by the camera and endlessly watchable as a result, her joyous pluck overshadowing the rest of the film’s murkier elements. That Disney, the studio behind the film, imagined its aspirational romcom hero as a rich businessman prowling Hollywood Boulevard for an escort is slightly maddening. That Pretty Woman somehow pulls it off... even more so.

George Clooney and Michelle Pfeiffer in 'One Fine Day' (Rex)

29. One Fine Day (1996)

Few romantic comedies are more nakedly aspirational about big-city jobs, capitalism and the social power of being busy than One Fine Day, a mid-Nineties comedy about two single parents thrust together when their hectic schedules mean their children miss the class trip. There are far too many big cellphones here, but Michelle Pfeiffer and an ER-era George Clooney, as the squabbling pair at its centre, must surely rank as one of the most beautiful romantic comedy couples in recent memory.

28. The Five-Year Engagement (2012)

This glossy, expensive romcom slipped under the radar slightly in 2012, despite the appealing presence of Emily Blunt and Jason Segel as a chronically engaged couple, and Alison Brie and a pre-Crossfit Chris Pratt as their besties. It’s Blunt’s vehicle, though, the film’s blend of spikiness and warmth mirroring her on-screen appeal. A veritable who’s who of funny Hollywood (including Mindy Kaling, Dakota Johnson, Kevin Hart, Randall Park and Kumail Nanjiani) also star.

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27. There’s Something About Mary (1998)

The gross-out comedy boom of the late 1990s and early 2000s is one of the more fascinating minor genre trends in recent decades. The Farrelly Brothers launched a cottage industry of films driven by cloying sentimentality and bodily functions. Most have aged poorly, but Cameron Diaz’s sunny dream girl radiance in There’s Something About Mary rescues the film from comic oblivion. She gives a daffy, entirely committed performance as the object of affection for a series of men each landing somewhere along a spectrum of depravity. It’s no wonder she became one of Hollywood’s biggest names in the aftermath.

26. Brown Sugar (2002)

As much a ludicrously beautiful romcom as it is a nostalgic snapshot of the New York hip-hop scene at the turn of the 21st century, Brown Sugar casts Taye Diggs as an A&R executive for a record label and Sanaa Lathan, magnetised to so many black romcoms during this time, as the editor for XXL Magazine. Friends since childhood, they’re perfect for one another, but involved with other people (the similarly too-beautiful-for-words real-life couple Boris Kodjoe and Nicole Ari Parker). Queen Latifah and Mos Def are their perfectly cast best friends, just to add to the film’s early-Noughties charm.

Adam Sandler in 'The Wedding Singer' (Rex)

25. The Wedding Singer (1998)

On paper, Adam Sandler and Drew Barrymore shouldn’t work so well together. They’re not quite opposites, with their comic zing not sourced from anything combative. Oddly, it’s their shared sensibilities that make them so transfixing on screen. Both are unabashedly sweet-natured, earnest and goofy movie stars who radiate heart. More than their middling reunion movie 50 First Dates or their woeful third go-around Blended, The Wedding Singer best captures their mutual affability. Soundtracked by an A to Z of 1980s pop classics, this is nostalgic, adorable and endlessly rewatchable.

24. Get Over It (2001)

The secret masterpiece of the teen movie boom birthed in 2001, and truthfully one of the last of that era, Get Over It grabs so many elements from its subgenre predecessors (a Shakespearean undercurrent, sexually excitable animals and cameos from one-hit-wonders of the time) that it’s a wonder it’s so brilliant. Ben Foster is the recently-dumped high school basketball player who signs up for the school play (a musical version of A Midsummer Night’s Dream, naturally) to woo back his ex, only to fall for the adorable younger sister (Kirsten Dunst) of his best friend. Surrounding them are an array of recognisable faces, including Mila Kunis, Martin Short, Zoe Saldana and the literal Sisqo, while it features one of the finest Backstreet Boys-era boyband spoofs this side of Josie and the Pussycats.

23. Gentlemen Prefer Blondes (1953)

Individual scenes from Gentlemen Prefer Blondes exist in cultural memory far more than the film does as a whole. There’s also a reason for that. Marilyn Monroe’s rendition of “Diamonds Are a Girl’s Best Friend” is frothy classic-Hollywood gorgeousness at its most primal, while her double act with Jane Russell is almost unfairly glamorous. But there’s also lovely sparkage to the film itself, its DNA found in many of the female-led comedies of the 21st century. Monroe and Russell are scrappy, ambitious women desperate to marry rich, and the film has a surprisingly sex-positive and self-aware quality to it that feels quietly radical for 1953. Casting dullards as the pair’s respective love interests makes total sense – these are women who could eat stupid men for breakfast, and the film knows it.

22. But I’m a Cheerleader (1999)

This satirical comedy set at a gay conversion camp has, quite clearly, a lot more than romance on its mind. But Jamie Babbit’s pink satin-coloured debut is most memorable for the brewing relationship between Clea DuVall’s Graham and Natasha Lyonne’s Megan. One is more in denial about their sexuality than the other, but they discover a mutual attraction while being held under the thumb of Cathy Moriarty’s conversion camp den mother – who, it should be said, is somehow more of a drag queen than her colleague (played by a de-glammed RuPaul).

Clea DuVall and Natasha Lyonne in 'But I'm a Cheerleader' (Rex)

21. Boomerang (1992)

The first black, mainstream romantic comedy to possess the same aspirational sheen as their white counterparts, Boomerang is a lively battle-of-the-sexes comedy with Eddie Murphy as a powerful, womanising advertising executive spurned by his female doppelganger (Robin Givens). Grace Jones, Eartha Kitt and a young Halle Berry make for wonderful supporting players, but Boomerang’s secret weapon is Givens, who gives a performance with so much spark that it’s enraging her volatile marriage to Mike Tyson overshadowed much of her acting career.

20. Four Weddings and a Funeral (1994)

An underwritten female lead in the form of Andie MacDowell’s Carrie is the only fly in this wry, warm-hearted ointment. Revolving around a group of friends as they attend – you guessed it – four weddings and a funeral, this film marks the first of many collaborations between Hugh Grant and screenwriter Richard Curtis. We can probably all agree that the hopeless, stuttering Charlie should have ended up with his best friend Fiona (Kristin Scott Thomas), but without his devastating indifference towards her, we would never have been blessed with one of the most magnanimous displays of unrequited love ever committed to film. The film’s worth your time, too, for its quietly progressive, heart-wrenching gay subplot.

19. 500 Days of Summer (2009)

Beloved and loathed in equal measure, 500 Days of Summer is notorious among a certain generation of young people who grew up with Joseph Gordon-Levitt and Zooey Deschanel as quirky hipster pin-ups. And it’s likewise already something of a nostalgic masterpiece, beloved in first-year university film studies classes if then loudly rejected come graduation. There’s a lot to say about where its allegiances lie (is Deschanel’s Summer the movie’s villain, or its rational, realistic hero?), but that discussion also swallows up appreciation for what is for the most part a clever and funny comedy, and a movie that sincerely celebrates the conventions of the genre.

Jennifer Garner in the original poster artwork for '13 Going on 30' (Universal)

18. 13 Going on 30 (2004)

If every romantic comedy is a fantasy, then 13 Going on 30 is the ultimate fantasy romcom. As if she has watched too many herself, unhappy tween Jenna Rink wishes she could be 30, flirty and thriving, and wakes up one morning a high-powered magazine editor who looks like Jennifer Garner, and whose dorky neighbour has transformed into Mark Ruffalo. By turns incredibly touching and genuinely funny, 13 Going on 30 is brought to life by Garner, who plays the adult-bodied Jenna as a guileless spark plug of self-doubt, glee and determination. Also features none of the weird child molesting undertones of Big, which we should forever be thankful for.

17. Moonstruck (1987)

Cher won a surprising yet entirely deserved Oscar for her work here, playing a dowdy Brooklyn widow engaged to an incredibly boring man, who decides to transform herself after falling for her soon-to-be brother-in-law (Nicolas Cage). Moonstruck is a love story and a traditional romcom, but it’s also the story of a woman throwing herself into the unknown and abandoning the kind of life she once felt resigned to. It is big, broad and richly romantic, with a touch of magical whimsy thrown in too.

16. Something’s Gotta Give (2003)

With Nora Ephron having slipped off this mortal coil, Nancy Meyers has more or less claimed her spot as Hollywood’s most dependable creator of sensitive and funny love stories set within designer kitchens. She has a largely great filmography, but Something’s Gotta Give remains her masterpiece. Diane Keaton and Jack Nicholson, both twinkling with lived-in Seventies-movie-star ease, play variations on their off-screen personas: her the exasperated neurotic, him the womanising letch. They’re thrown together in the Hamptons, stumble upon an unexpected attraction, and wrestle with what it all means. Keanu Reeves, as Keaton’s doctor and secondary love interest, is additionally a dream.

15. Roman Holiday (1953)

A perfect encapsulation of the Fifties, specifically the allure of the European jet-set, the idealised rat-a-tat-tat magic of big-city journalists, and the otherworldly regality of Audrey Hepburn, Roman Holiday is more of a time machine than most of the films here. But it’s also a true-blue classic, its “famous woman paired with ordinary man” plot inspiring everything from Notting Hill to The Lizzie McGuire Movie, and appropriately beloved as a result. There’s no Hilary Duff, obviously, but we won’t hold that against it.

14. Roxanne (1987)

One of the more underrated leading men in the romantic comedy genre is Steve Martin, whose CV is littered with sweet love stories as swoon-worthy as they are surreal and fantastical. The Lonely Guy and LA Story have their charms, but Roxanne, his 1980s spin on Cyrano de Bergerac, is his strongest, gentlest romcom work.

13. Love Actually (2003)

Most great romcoms are lucky enough to have one stand-out set piece that becomes embedded in the cultural landscape. Love Actually, the annually inescapable Christmas romcom behemoth from Richard Curtis, has about six or seven. Because it’s as famous as it is, Love Actually oddly has a tendency to be underrated, dismissed as too cutesy or misogynist, too awkwardly Blairite in its politics. And all of that, in fairness, is true. But it’s also a real classic of the form – masterfully structured, endlessly watchable, and filled with familiar faces, sweet romances and heartache. It’s love in all its colours, often cringeworthy, sometimes monstrous, but always compelling to watch unfold.

Andrew Lincoln in ‘Love Actually’ (Re (Rex Features)

12. Serendipity (2001)

There’s a great Arrested Development storyline in which Jason Bateman’s character doesn’t realise his love interest is mentally ill because she’s an eccentric British woman who looks like Charlize Theron. It may or may not have been inspired by Serendipity, the greatest romantic comedy ever made about a deranged and beautiful Englishwoman fixated on fate, chance and the cosmos. Kate Beckinsale and John Cusack meet by chance at Christmas time in New York, share a blissful evening together but then go their separate ways, Beckinsale sure that they must only date if the universe doesn’t otherwise intervene. Some time later, the pair are engaged to other people, but can’t shake their memories of that fateful Christmas Eve. Sweet, cosy and completely irresistible, Serendipity is a rare Christmas movie/romantic comedy twofer and features two lovely performances at its centre. Absolutely bonkers, to be fair, but few films on this list aren’t.

11. Bridget Jones’s Diary (2001)

It is funny in hindsight that there was such a stink over the casting of the Texan Renee Zellweger as the very English Bridget Jones. Because could you now imagine anyone else playing her? Her accent flawless (in that very prim, written-by-Richard-Curtis way), Zellweger similarly nails the spirited, neurotic melancholy that makes Bridget such a likeable character, despite all the reasons we probably wouldn’t be able to stand her in reality. Like most of Curtis’s work, there is a lovely comfort to Bridget Jones, full as it is of slapstick, silly jumpers and new-millennium London, featuring Colin Firth and Hugh Grant as “adorable dork” and “magnificent bastard”, respectively, and a perfect Christmas finale. It’s truly one of the best of the genre.

10. 10 Things I Hate About You (1999)

Gut-wrenching to watch in the wake of Heath Ledger’s death, but still one of the smartest, most convincingly heartwarming comedies of the last 20 years. Ledger and Julia Stiles are a pair of “unappealing” high schoolers whose romance is engineered by Stiles’s younger sister, who can only date once she does. There is much to love here, from the film’s feminist politics (10 Things remains the holy grail of its era, in that regard) to its delightful supporting cast. But it’s Ledger and Stiles that burn the screen. Their chemistry is so authentic, charming and sexy that it’s almost uncomfortable to watch, with only the fact that they’re both ridiculously beautiful encouraging you never to turn away.

9. The Apartment (1960)

Christmas has never been better presented in all its melancholy splendour than in Billy Wilder’s The Apartment, with two lonely souls both left dispirited by the holiday season yet finding each other hopelessly up in one another’s lives. Jack Lemmon is unsurprisingly wonderful as one half of the film’s central twosome, who loans out his apartment to his lecherous bosses so they can conduct their affairs, but it is Shirley MacLaine who provides the film with its heart – she is bruised and brittle but eager for connection, and perfectly embodies the dizzying emotions of the winter season.

Jack Lemmon and Shirley MacLaine in 'The Apartment' (Rex)

8. My Best Friend’s Wedding (1997)

Considering how many people adore My Best Friend’s Wedding, it’s always surprising to re-discover how monstrous its apparent heroine is. Julia Roberts has had better-received roles before and since, but there’s something fascinatingly daring about her work here, playing a single woman in love with her best friend and determined to destroy his wedding to a lovely if naive rich girl she has decided is evil. Cameron Diaz, as the bride-to-be, is an adorable revelation, Rupert Everett a hoot as Roberts’s then-radical “gay best friend”. And the sheer darkness on display here, mixed with that funny and expensive Nineties-romcom sheen, makes it one of the most intriguing romcoms in history, and secretly one of its very best.

7. Notting Hill (1999)

You could argue that June and Joseph – the dead, park bench couple – have the most poignant love story in this film, but the one between world-famous movie star Anna (Julia Roberts) and very-much-not-famous bookshop owner Will (Hugh Grant at perhaps his most charming, foppish and floppy-haired) comes a close second.

6. Groundhog Day (1993)

It’s easy to forget that Groundhog Day is unashamedly romantic. At its heart is that incredible concept: Bill Murray’s obnoxious weatherman is stuck in a time loop, so takes the time to better himself. Surrounding it is a love story between Murray’s character and the TV producer who initially can’t stand him (Andie MacDowell), and how personal betterment makes every trial and tribulation somehow worthwhile.

John Cusack in 'Say Anything...' (Fox)

5. Say Anything… (1989)

Sometimes all it takes to forgive a romcom of its creepy undercurrent is a pair of beautiful movie stars with impeccable chemistry. In fairness, that occurs throughout the romantic comedy genre, but it’s especially noticeable in Cameron Crowe’s Say Anything... This is a story about fixation and co-dependency and poor Ione Skye stuck in the middle of two incredibly needy men, but Crowe somehow makes Say Anything... strikingly romantic anyway. It feels truthful, with love depicted as messy and ludicrous and sometimes unfortunate, but worth it for how good it feels otherwise. Skye and John Cusack are wonderful together; the film takes its time allowing us to fall in love with them just as they’re falling in love with each other. And that boombox scene is iconic for a reason.

4. The Philadelphia Story (1940)

A fizzy treasure of a comedy that set the tone for much of what came after it, The Philadelphia Story casts a never-haughtier Katharine Hepburn as a feisty heiress stuck between three men: her dull fiance (John Howard), a prickly journalist (James Stewart) and the ex (Cary Grant) still hopelessly in love with her. Everyone speaks incredibly fast, romantic tribulations occur in elegant mansion estates and the film’s central trio embody an impossible movie-star glamour you can’t help but begin to miss as soon as they appear on screen.

3. Annie Hall (1977)

We know. Where you stand on Woody Allen’s work, particularly the stuff not revolving around the apparent inability of young women to resist the allure of a scrawny, bespectacled middle-aged neurotic, is one of those endless pop culture questions we’ve all asked ourselves in recent years. If anything, though, watch Annie Hall for Diane Keaton at her most Diane Keatonish – daffy, stylish and impossibly cool, she becomes so much more than an idealised fantasy figure through sheer force of will. Annie Hall, admittedly, is a masterpiece, if you can look past the obvious.

2. You’ve Got Mail (1998)

While Tom Hanks and Meg Ryan’s most famous prior romcom collaboration, 1993’s Sleepless in Seattle, has a dark melancholy that makes it less immediately pleasurable to watch, their 1998 reunion in You’ve Got Mail is the kind of movie built for comforting rewatches beneath a blanket. Or at least once every year at Christmas. The pair play sworn enemies waged in a war over the future of Ryan’s ludicrously serene independent book shop, but find love when interacting anonymously online. Despite the dial-up modems and archaic dialogue (“What’s email?” everyone seems on the verge of asking), You’ve Got Mail hasn’t aged poorly, proving how timeless chemistry-driven love stories between beautiful movie stars can be. And considering how brilliant Ryan is here, oscillating between tough strength and soft vulnerability, it is no surprise that she is still regarded as the star most associated with the genre.

1. When Harry Met Sally (1989)

Truthfully, it couldn’t be anything else. Not only did When Harry Met Sally kickstart the romcom boom that dominated the Nineties, it also invented much of what we recognise today as cliches: from the sardonic best friend (played to perfection by Carrie Fisher), to the late-night phone calls while watching old movies, the Christmas/New Year’s climax, the “neurotic Jewish man”/“shiksa goddess woman” pairing at its centre, and the hilarious honesty when it comes to sex, never bettered than in the film’s iconic diner-orgasm scene. Romantic comedies are only cliched because When Harry Met Sally set such a glorious benchmark for why these films work in the modern era, assisted by Billy Crystal and Meg Ryan at their most golden, and a gorgeously structured script that leaps through time, written by the queen of the genre herself, Nora Ephron. Nothing will ever better this.

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