20 of the greatest rom-coms for lovesick romantics
Weddings, sardonic best friends and a lot of Julia Roberts... Adam White reveals the 20 greatest romantic comedies
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. 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?
20
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.
19
She’s All That (1999)
There are a few moments in this high school re-telling of George Bernard Shaw’s Pygmalion — in which, due to an elaborate bet, popular jock Zach (Freddie Prinze Jr) attempts to turn artsy nerd Laney Boggs (Rachael Leigh Cook) into the prom queen in six weeks — that pull the rug out from under your feet. Well above your average high-school romcom.
18
27 Dresses (2008)
Partly because she was its last high-profile “queen”, Katherine Heigl has often been positioned as the actor that killed the romantic comedy. Which is unfair for a host of reasons, but specifically because both Knocked Up and 27 Dresses are such pristine examples of how great the romcom can still be. We truly didn’t appreciate her at the time.
17 Playing by Heart (1998)
Not strictly a romantic comedy, buoyed as it is by serious drama involving everything from infidelity to Aids, Playing by Heart is one of those talky, interconnected, Robert Altman-esque indies that dominated so much of American cinema in the Nineties. But the reason it’s here is because two of its many storylines feature lighter pairings that appear unlikely on paper, but somehow become incredibly compelling and tender in execution.
16
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. One of the most beautiful romantic comedy couples in recent memory.
15
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 (Charlize Theron) as he is to himself.
14
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.
13 Forgetting Sarah Marshall (2008)
Of the post-Judd Apatow era of romantic comedies, this the best — nicely balancing genuine sweetness and pathos (Mila Kunis is at the peak of her adorability as the love interest) with A-grade smut. There’s also a puppet musical thrown in for good measure, which is never not welcome.
12
The Break-Up (2006)
Very loudly not fun, but still something quietly extraordinary, The Break-Up is a romcom in reverse, with Jennifer Aniston and Vince Vaughn a couple at the end of their tether, who really shouldn’t be together and break-up before the opening credits roll and then muddle through the following 90 minutes figuring out what to do next.
11 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. One of the most magnanimous displays of unrequited love ever committed to film.
10
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.
It’s a real classic of the form — masterfully structured, endlessly watchable and filled with familiar faces, sweet romances and heartache.
9
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.
8
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.
7
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 heart-warming comedies of the last 20 years. Ledger and Julia Stiles are a pair of “unappealremains ing” high schoolers whose romance is engineered by Stiles’s younger sister, who can only date once she does. Ledger and Stiles burn up the screen.
6
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 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.
5 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 (Cameron Diaz) she has decided is evil.
4
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-notfamous bookshop owner Will (Hugh Grant at perhaps his most charming, foppish and floppy-haired) comes a close second.
3
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 in love with her. The film’s central trio embody an impossible movie-star glamour.
2
Annie Hall (1977)
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.
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. Romantic comedies are only cliched because When Harry Met Sally set such a glorious benchmark.