Depending on who you ask, Valentine’s Day is either the sole thing that makes February bearable or Hallmark-sponsored hell. Whichever side of the debate you fall on, you can find validation – or solace – in a good rom-com. Below, Vogue rounds up 30 of the best.
Palm Springs (2020)
By no means is Palm Springs a traditional rom-com, but that’s what we love about it. The film features Andy Samberg and Cristin Milioti as a pair of strangers who meet at a wedding and end up stuck in the same... cosmic time loop? Yeah, to be honest, we don’t really get it either, but luckily, the film is as charming as it is weird. (Which is to say, very.) By the way, the chemistry between Samberg and Milioti is off the charts, even as they’re hurtling through time and space.
Crossing Delancey (1988)
In Joan Micklin Silver’s Crossing Delancey, Amy Irving is Isabelle “Izzy” Grossman, a woman who has it all – dear friends, an interesting job, a rent-controlled Manhattan apartment – except, to her grandmother Ida’s chagrin, a husband. While Izzy lusts after Anton (Jeroen Krabbé), a worldly, married author she meets at the bookstore where she works, Ida sets her up with a matchmaker, who in turn introduces Izzy to Sam (Peter Riegert), the owner of a nearby pickle shop. Though Izzy resists his unassuming charms at first, passing Sam off to a girlfriend, eventually, realisations and regrets give way to a happy reconciliation.
Something Wild (1986)
Before Jonathan Demme decided to win an Oscar and scare the pants off an entire generation with The Silence of the Lambs, he was an ’80s funnyman. And this is his best work. It’s the story of a mild-mannered exec (played by Jeff Daniels), whose sedentary life is turned upside down by the wildly adventurous, somewhat grifting Lulu (Melanie Griffith) – whose chequered past includes a criminal ex-boyfriend played by Ray Liotta. The idea of a “crazy” girl coming in and turning a straight man’s existence topsy-turvy is repeated countless times in this genre, from Bringing Up Baby to The Girl Next Door. Demme’s alchemy here is to infuse the trope with unpredictability. The comedy keeps us on the edge of our seats by compounding the will-they-won’t-they question with sudden breaks into violence, threats, or chase. Rom-coms don’t get more exciting than this.
Rushmore (1998)
This is Wes Anderson’s most stylish movie, and perhaps his best. (Like all Anderson’s best work, this was cowritten with Owen Wilson.) Max Fischer (Jason Schwartzman) is a scholarship student at a private school. His academics are dismal, but he’s game for any and all extracurriculars, especially the over-the-top plays he produces and directs. He gets into a contest for the affections of a widowed first-grade teacher with a local industrialist, and his newfound mentor, Herman Blume (Bill Murray). Several phenomenal executions come together in this film, including the ensemble cast, the just-on-this-side-of-believable production design, and an absolutely killer classic-rock soundtrack. But what pushes it above the rest is the utter drive of both Max and Herman, as love and competition gain primacy over every aspect of their lives. They’re both willing to burn the village to save it, which is simultaneously hilarious to watch and cathartic to anyone who’s ever had a crush.
Emma (2020)
There’s really no improving on Jane Austen... but may we be so bold as to say that Autumn de Wilde’s adaptation of the 1815 novel gets pretty darn close? Anya Taylor-Joy shines as the titular character, and her battle of wits with Knightley (Johnny Flynn) imbues the familiar story with endless fun and froth. Side note: do film costumes get any better?
Me And You And Everyone We Know (2005)
One of the quirkier additions to this list – and it would be, coming from the wonderfully wacky mind of Miranda July – Me and You and Everyone We Know is about both our need to connect, and how completely terrifying true intimacy can be. There’s Christine (July) and Richard (John Hawkes), a video artist and a shoe salesman who seem to have something going until Richard cuts it off; Richard’s six-year-old son, Robby (Brandon Ratcliff), and the older woman (Tracy Wright) with whom he begins a flirtation online; two teenage girls (Natasha Slayton and Najarra Townsend) engaged in a troubling back-and-forth with their neighbour (Brad William Henke); and several other strange souls tentatively entering each other’s orbits. “July’s debut feature wasn’t the first movie about the internet,” IndieWire’s David Ehrlich observed of the film in 2020, “but it may have been the first to recognise how we’d express ourselves through it, and how the utopian promise of ‘social media’ would so plainly reveal how scared we are of getting close to each other.”
Barefoot In The Park (1967)
Adapted from the play by Neil Simon – a master of the genre on Broadway – Gene Saks’s Barefoot in the Park stars Robert Redford and Jane Fonda as the newlyweds Paul and Corie Bratter; he sort of a stiff, she the more easygoing and optimistic one. Spanning the couple’s first few days in their new apartment – a leaky, creaky walk-up in Greenwich Village – Barefoot is somewhat less about falling in love (although there is a charming subplot concerning Corie’s mother and one of their neighbours, Victor Velasco) than endeavouring to stay in it.
Gentlemen Prefer Blondes (1953)
In this glittering Howard Hawks comedy – the one that gave us Marilyn Monroe’s rendition of “Diamonds Are a Girl’s Best Friend”, God bless it – Monroe and Jane Russell star as Lorelei Lee and Dorothy Shaw, two best friends-slash-showgirls who know exactly what they want: to marry rich (Lorelei) and handsome (Dorothy). But that, it turns out, is not as simple as it sounds – especially when a meddling would-be father-in-law, a private detective, and the elderly owner of a diamond mine get involved.
But I’m A Cheerleader (2000)
Directed by Jamie Babbit, this dark comedy centres around religious high-school cheerleader Megan (Natasha Lyonne) being sent away to “straight camp”, where the staff attempts to turn her and her fellow queer teens towards the Lord. Unfortunately for them, that doesn’t quite work out, as Megan falls hard for her fellow female camper Graham (Clea Duvall). Even two decades later, But I’m a Cheerleader holds up as one of the campiest, sweetest, and – to be frank – only lesbian rom-coms out there.
The Big Sick (2017)
This one isn’t quite a romantic comedy in the traditional sense – the female romantic lead spends most of the film in a coma – but it will give you a new appreciation for what it means to truly love someone. Comedian and actor Kumail Nanjiani shines as the film’s star, and his fingerprints are all over the film; it’s more or less the true story of how he met his wife, writer Emily V Gordon, and the two co-authored the script.
Crazy Rich Asians (2018)
Based on the novel of the same name by Kevin Kwan, this film takes a deep dive into the splashy, sparkling lives of Singapore’s elite, with the story of Rachel (Constance Wu) who falls in love with Nick (Henry Golding) before learning that his family, headed by terrifying matriarch Eleanor (Michelle Yeoh), is among the richest in Singapore. The central question of whether love can conquer money is almost outshone by the film’s dazzling surroundings as well as Rachel’s nouveau riche friends, played perfectly by Awkwafina and Ken Jeong.
Broadcast News (1987)
In the mid to late ’80s, there was nothing bigger than TV news and James L Brooks, and Broadcast News was their meeting ground. After the slap-happy, very silly, and very male comedies of the late ’70s and early ’80s (think Animal House, Porky’s, and Revenge of the Nerds), and alongside epic big-budget projects like Ghostbusters and the original Indiana Jones, Brooks continued to redefine what rom-coms could be with this sprawling, occasionally dramatic, but never overly serious workplace comedy. We root for Albert Brooks’s Aaron Altman, the brainy, nervous, serious journalist who competes for the affections of neurotic producer Jane Craig (Holly Hunter) against the impossibly polished (and intellectually inferior) Tom Grunick (William Hurt). Brooks is the producer behind films like Bottle Rocket, Say Anything, and Big, and TV series like Mary Tyler Moore, Taxi, and The Simpsons. No one knows how to get at our hearts – thoughtfully, gracefully, and with humour – like him.
The Philadelphia Story (1940)
The credits of The Philadelphia Story read like something out of a dream: Cary Grant and Jimmy Stewart vying for the love of Katharine Hepburn. It’s produced by Joseph L Mankiewicz (writer of All About Eve and Cleopatra), and directed by George Cukor (who made 1954’s A Star Is Born, Justine, and My Fair Lady, and once told Marilyn Monroe, “That will be just fine, darling,” when, about to film a skinny-dipping scene for Something’s Got to Give, she expressed her concern that she only knew how to doggy-paddle). The Philadelphia Story relies on some dependable tropes – lovers who’ve fallen out, a will-they-or-won’t-they-get-back-together situation – that have provided romantic tension from A Midsummer Night’s Dream to Crazy, Stupid, Love. But it’s Hepburn, aiming for a comeback following some serious bombs, and her witty repartee with her two love interests, Grant (her yacht-designing reformed bad boy of an ex-husband) and Stewart (a tabloid reporter), that is the movie’s bread and butter. The Main Line has never been so well represented.
Lost In Translation (2003)
There was never any doubt that Scarlett Johansson was going to be a megastar, but Sofia Coppola’s movie – about the lonely wife of a photographer who befriends an over-the-hill movie star (Bill Murray) while visiting Tokyo – is what made the world stand up and realise we were dealing with a serious actor. Like many of the films on this list, Lost in Translation takes place in a bourgeois universe, where the greatest thing at risk is someone’s heart or future emotional happiness, but few films have so effectively crystalised the alienation of both travel and marriage as well as the difficulties of post-collegiate, and then midlife, malaise. The older man and the younger woman don’t so much meet-cute as crash into each other, picking up each other’s pieces, redeeming each other’s lives as they navigate their surreal setting. It’s a match made in heaven – and, without spoiling anything, their goodbye scene is among the best in Hollywood history.
Silver Linings Playbook (2013)
Ah, Silver Linings Playbook. It will make you laugh, it will make you cry, it will make you relive Jennifer Lawrence falling up the stairs at the Oscars while accepting her Best Actress statuette. Jokes aside, this is a wonderfully empathetic depiction of two characters who – in spite of suffering from mental health problems – are able to learn to be each other’s saving grace. Bradley Cooper is excellent as bipolar teacher Pat – who, to quote Lawrence’s Tiffany, says more inappropriate things than appropriate things – but it’s Robert De Niro as Pat Senior that will absolutely melt your heart.
Moonstruck (1987)
Cher plays a widowed bookkeeper in Brooklyn Heights confronting her parents’ infidelity (and fallibility) who – whoops! – falls for her fiancé’s younger brother (Nicolas Cage), who sports a prosthetic wooden hand after an accident with a bread slicer. Their first night together produces one of the great moments in the annals of rom-coms. When Cage tells Cher he loves her, she slaps him, saying: “Snap out of it!” The film portrays a New York that doesn’t really exist anymore – for one thing, Brooklyn Heights is full of bankers now. It’s a window to another time, when marriage meant something different in male-dominated second-generation immigrant families, and the challenges Cher’s character places to the social order are both important and revelatory (she won an Oscar for her efforts). You end up cheering not just for her romance, but also for an entire insurgency.
Roman Holiday (1953)
There’s a wonderful moment in Roman Holiday – the story of a European princess, played by Audrey Hepburn, who tires of her duties and runs away from her handlers while visiting Rome – when Joe (Gregory Peck), a reporter showing her the city, puts his arm in the Mouth of Truth (a statue that supposedly bites off the hand of liars) and removes it with his hand missing. The princess screams – Hepburn was apparently not acting here – and then recovers. It’s a metaphoric yawp for all that a romantic comedy should be. It’s being taken by surprise, taken by a stranger, the discovery of a new side of oneself while falling for someone else. And that’s just one moment!
Groundhog Day (1993)
One of the few rom-coms that comes with both a stamp of approval from your philosophy professor and the Tony reaches of Broadway. A cynical Pittsburgh weatherman (Bill Murray) is sent to Punxsutawney, Pennsylvania, with his producer, Rita (Andie MacDowell), on a dead-end assignment: to cover Groundhog Day. And boy, is it a dead end. Murray gets stuck there, not just in a snowstorm, mind you, but in a continuous loop, where no matter what he does – including suicide – he wakes up in the same hotel on the same day. At first, the weatherman is predictably bummed, but eventually, he uses all the information he’s picked up living the same day over and over to better himself and the lives of those around him, eventually impressing Rita with his change of personality. Watching Bill Murray is fun, watching Bill Murray struggle is really fun, and watching Bill Murray caught in a space-time logjam, wrestling with moral philosophy while pursuing Andie MacDowell is the most fun.
Bringing Up Baby (1938)
Here’s how cute rom-coms were in the 1930s: the entire plot rests on a dog burying a bone of a brontosaurus. Katharine Hepburn, whom the movie was written for, plays a whimsical, adorable socialite who has become besotted with an otherwise engaged (literally and figuratively) palaeontologist, played by Cary Grant, and is trying to keep him around so he won’t go marry some pill. Her strategy for doing this is to invite him to her house so that he can help her bring a baby leopard to the city. (Later, the dog and the leopard wrestle.) This is what we call a screwball comedy. It’s also priceless, with Hepburn peppering Grant in her sweet, Gatling gun style, and Grant, playing stiff, as if any man, never mind a mild-mannered palaeontologist, could ever resist such wiles.
How Stella Got Her Groove Back (1998)
The movie that inspired 90 per cent of vacation hook-up jokes since 1998 (but seriously, we need to talk about Taye Diggs in a puka shell necklace – the man can make anything look good). Workaholic executive and single mom Stella (Angela Bassett) gets more than she bargains for when her best friend, played by Whoopi Goldberg, convinces her to take a much-deserved Caribbean vacation. Cheeky, subversive, and sexy as hell, this movie turned the tables on so many male-dominated rom-coms (courtesy of one very hot and heavy match-up between Bassett and Diggs, playing some 20 years her junior) – and passes the Bechdel test with flying colours. One of the very few rom-coms to do so.
Say Anything... (1989)
If for no other reason, you need to see this movie so you’ll understand what it means when someone holds a ghetto blaster over his head outside the window of the woman he loves. Say Anything... doesn’t end at the big dance. This movie, from director Cameron Crowe (and produced by James L Brooks), is far too sophisticated for such a middling finale. And it’s too busy diving into the angsty, all-consuming, awkward challenge that is young love, as embodied by consummate underdog Lloyd Dobler (John Cusack) and his attempts to woo the beautiful valedictorian Diane Court (Ione Skye).
Top Five (2014)
Think of it as Before Sunset meets Funny People, with New York taking the place of Paris. If that notion produces a little eye roll, get those peepers back down, and then on the screen before you miss some laughs. Rosario Dawson plays a New York Times journalist tasked with interviewing a hugely famous comedian, played by Chris Rock, who is attempting to take his career in a new direction (courtesy of an ill-advised serious film about a Haitian revolutionary). Like Roman Holiday before it, this is a film rooted in our society’s placement of, and expectations for, certain figures (a celebrity and a princess, respectively). In both cases, the journalist finds the human being inside of their famous subject, falling for them while trying not to fall for their shtick, or what they represent. As the pair make their way through Manhattan – with visits from Jerry Seinfeld, radio hosts Opie and Anthony, Whoopi Goldberg, and a fantastic supporting job from the ageless Gabrielle Union, playing a reality TV starlet – we can’t help but get on board with their journey.
Harold And Maude (1971)
There’s a question that lingers throughout most of Harold and Maude – the story of a death-obsessed young man (he enjoys driving a hearse, attending funerals, and faking his suicide) who falls for a much, much older woman – are these two going to get it on? It sounds sophomoric, but it’s actually essential. Harold and Maude are separated by approximately 60 years; for the movie to hit home, for us to believe that love is truly about what we share, not what we look like or other aesthetic values, we have to believe a genuine attraction has formed. No one prodded existentialism (especially in films deemed “romantic”) like director Hal Ashby, and Harold and Maude is no exception. The darkly funny tale will leave you questioning just what is important to you in your own conception of love – and, moreover, in your life.
Coming To America (1988)
It’s unfair that Eddie Murphy only has one entry on this list. The guy ruled the ’80s and made some of the era’s great comedies – Trading Places, Beverly Hills Cop, 48 Hrs – but this is really the only one where the romance narrative rules supreme. In short: Murphy plays the prince of a fictional African nation who is unsure about his arranged marriage, and so heads to what he suspects will be greener pastures in search of his queen. So where better to start than Queens, New York? Essentially slumming it with his best friend (a terrific Arsenio Hall), Murphy’s character finds work at a McDonald’s-type restaurant where he falls in love with the owner’s daughter, a woman who just might fit the bill. It’s a super simple story that elicits big laughs in every scene, but it’s also a clever send-up of class and race that simultaneously owns itself as perhaps the ultimate Reaganite comedy. If you are rich and follow your heart, you can be even richer!
Juno (2007)
Life’s not perfect, but it can be most endearing – that’s the takeaway, anyway, from Jason Reitman’s nuanced teen comedy Juno. Elliot Page gave their breakout performance as the titular pregnant-by-accident teen who soldiers on through high school while preparing to give her baby up for adoption to a painfully needy rich couple (or “baby-starved wingnuts”, as her father calls them.) Juno’s honesty and her backward love story with the adorably nerdy Paulie (Michael Cera) remind us of the true meaning of being cool and that heartache can resolve itself into a tender, resilient future.
Working Girl (1988)
First, consider the cast: Melanie Griffith, Harrison Ford – who owned the ’80s in Hollywood and made this his only rom-com – Sigourney Weaver, Joan Cusack, Oliver Platt, and Alec Baldwin (at his douchiest). Next, look at the director: Mike Nichols – if there is a pantheon for romantic films, he probably has Zeus’s seat. Finally, the shoulder pads; my God, the shoulder pads. Were doorways made wider in the 1980s? Adventures in Babysitting aside, this movie is really as feminist as mainstream movies got in the ’80s. Melanie Griffith plays Tess McGill, a wily business school graduate working as a secretary at an investment bank with such memorable one-liners as “I have a head for business and a bod for sin.” When her boss (Weaver) steals her idea for a merger and then ends up out of commission (temporarily bedridden after a ski accident), Tess rises to the occasion: scheming with the support of her friends and maybe-lover (Ford), conniving, flirting, and using some good old-fashioned elbow grease to outwit her superiors, beat the boys, and claim the position she’s rightfully earned. Griffith is miraculous (one critic compared her to Marilyn Monroe; younger viewers might see a mould for Alicia Silverstone’s Cher), taking a role that could have just been “cute” and elevating it to nuanced and beguiling. That’s what this film is – so much so, we’ll forgive you if, after watching it, you suddenly have a soft spot for shoulder pads.
Jerry Maguire (1996)
Cameron Crowe has a couple of films on this list (Almost Famous was close, but ultimately more coming-of-age than comedy) with good reason: he understands people and how they tick. Despite its memorably demonstrative, over-the-top lines, like, “You complete me” and, “Show me the money”, this is ultimately a movie about how people really fall in love. Sure, Renée Zellweger loves Tom Cruise from the beginning – it’s a movie, after all, and he is Tom Cruise – but what Jerry Maguire gets to is what happens after that first kiss, after the honeymoon period, when we have to learn about the other person as a person and not just see them and their adorable puppy (or in this case, an adorable son, played by Jonathan Lipnicki) as an escape or alternative from our own lives.
Two Days In Paris (2007)
For sheer hilarious, messy, complicated realism, Two Days in Paris takes the prize. The brilliant and surprising Julie Delpy writes, directs, and stars as Marion, a young Frenchwoman who has brought her American boyfriend Jack (Adam Goldberg) to her hometown en route from a trip to Venice. They struggle through misunderstandings, language barriers, cultural clashes, encounters with Marion’s many ex-boyfriends, and her unruly parents (played by Delpy's real-life mother and father, actors Marie Pillet and Albert Delpy), and barely come out the other side. The moral, as Marion paraphrases to Jack: “It’s not easy being in a relationship, much less to truly know the other one and accept them as they are with all their flaws and baggage.” It may not be easy, but it’s highly entertaining to watch them try.
Reality Bites (1994)
In what was then a cult hit and is now a piece of ’90s nostalgia catnip, a post-Edward Scissorhands Winona Ryder plays Lelaina, an aspiring documentarian assisting an obnoxious TV host in Houston. She and grungy, Generation X friends – played by Steve Zahn, Janeane Garofolo, and a simmering Ethan Hawke (who may be more than just a friend) – are just trying to figure out who they are, and what they want in life. In Ben Stiller’s feature directorial debut, he also plays a TV executive whose budding romance with Lelaina and interest in her work brings the real world crashing into their post-collegiate hipster existence. Aside from the nonstop ’90s fashion buffet that is Winona’s wardrobe (mom jeans, crop tops, babydoll dresses, cardigans, men’s shirts, blazers), there’s also love and heartbreak, sex, betrayal, Lisa Loeb, Dickies, pizza, and lines like, “He’s so cheesy, I can’t watch him without crackers.” What else do we want, really?
Muriel’s Wedding (1994)
Muriel (Toni Collette), a daydreamer and the target of the bitchy girls she considers her friends, wants nothing more than to get out of her small town and away from her awful father, move to Sydney, and get married. When she makes off with her parents’ savings, reunites with a fellow outcast from her town, and is offered the chance to marry a gorgeous South African swimmer who needs a visa, she can make her dreams come true. As much a coming-of-age story as a rom-com (Muriel may be in her twenties, but she has much growing up to do), this film does a brilliant job of cutting the legs out from underneath our expectations by giving us exactly what we’ve always wanted and tying us up in the strings attached.
