The 10 best rom-coms of all-time, by decade (May 2023)

The rom-com is one of the most popular genres in all of cinema, so here’s our list of the best romantic comedies from each decade since the 1930s. Including a new entry from this decade!

Who doesn’t love a rom-com? Whether focussing on the com, or the rom, or a combination of both, some make us feel good about love, while others pick us up while we are down.

There are thousands to choose from, so to narrow this list down, we’ve picked our favorite rom-com from each decade since the 1930s, as of May 2023.

We’ve also added additional runners-up, giving us a grand total of 60 of the very best rom-coms.

1930s rom-com: It Happened One Night

Spoilt heiress Ellie elopes with a pilot whom her father believes is only interested in her money. When the pair become separated, Ellie travels cross-country to find him. But along the way she is thrust together with newspaper man Peter, who recognizes Ellie, and persuades her to give him an exclusive in exchange for help reuniting the couple. But then, sparks start flying between Ellie and Peter.

The very definition of a screwball comedy, It Happened One Night also had pretty adult themes, and was released just four months before cinema became watered down by the Motion Picture Production Code. A hit with audiences and critics alike, the film also made history by winning the big five Academy Awards – Picture, Director (Frank Capra), Adapted Screenplay (Robert Riskin), Actor (Clark Gable), and Actress (Claudette Colbert). The only other films to achieve that feat are One Flew Over the Cuckoo’s Nest and The Silence of the Lambs, neither of which made this list, for obvious reasons.

Runner-Up: Bringing Up Baby

Cary Grant, Katherine Hepburn, and a leopard – what’s not to like?

4 more great rom-coms from the 1930s: My Man Godfrey, Bringing Up Baby, Pygmalian, Heaven Can Wait, Platinum Blonde.

1940s rom-com: I Know Where I’m Going!

I Know Where I’m Going is It Happened One Night in reverse, in that heroine Joan is travelling from Manchester to the Island of Kiloran to marry a rich industrialist. But bad weather strands her on the nearby Isle of Mull, and a series of strange ocurrances keep her there. She meets Naval officer Torquil while trying to continue her journey, and while they initially clash, the pair soon start to fall for each other, the drama coming to a head when they finally make it to Mull.

The work of Michael Powell and Emeric Pressburger – perhaps the UK’s greatest ever filmmakers – this one does indeed follow the It Happened One Night playbook. But what sets it apart is the sense of magic that fills every frame, with characters, buildings, and scenery all touched by something otherworldly. As the star-crossed lovers, there’s also magic between Wendy Hiller and Roger Livesey.

Runner-Up: His Girl Friday.

Cary Grant again, this time using his journalism skills to keep his reporter ex from remarrying.

4 more great rom-coms from the 1940s: The Shop Around the Corner, The Philadelphia Story, Blithe Spirit, Adam’s Rib.

1950s rom-com: Some Like It Hot

A pair of Chicago jazz musicians – Joe and Jerry – witness a gangland murder, so disguise themselves as women, and leave town on a train with an all-female band. While working their way towards Miami, Joe – now Josephine – falls for a ukulele player called Sugar Kane. While a millionaire called Osgood Fielding III falls for Jerry, whom he believes to be a woman called Daphne. Much mistaken identity – and a good deal of confusion – ensues.

Some of the films on this list feature more romance than comedy, but Some Like it Hot definitely delivers comedy over romance. Tony Curtis and Jack Lemon are a riot at the cross-dressers in question, while Marilyn Monroe burns up the screen as the object of their affections. The brilliant Billy Wilder script is filled with zingers, while it also features one of the greatest final lines in film history.

Runner-Up: Roman Holiday

Audrey Hepburn plays a bored heiress who falls for an American newsman in romantic Rome.

4 more great rom-coms from the 1950s: Gigi, Sabrina, The Quiet Man, Lady and the Tramp.

1960s rom-com: The Graduate

Benjamin Braddock is a 21-year-old college graduate who feels disconnected from society, and has no idea what to do with his life. Then he meets a 40-something friend of his parents – Mrs. Robinson – and so begins an awkward affair. Ben is soon forced on a date with Elaine – Robinson’s daughter – and while he initially tries to sabotage their time together, Braddock is soon falling for his lover’s daughter.

The 1960s were a more sexually permissive time, and many movies of the period reflected that, most notably The Graduate. Based on a sharp, cynical script by Buck Henry and Calder Willingham, the film won Mike Nichols an Academy Award for directing, and made a global superstar of Dustin Hoffman. While the music – by Simon and Garfunkel – is as memorable as the film.

Runner-Up: The Apartment

This one might be even darker than The Graduate, with Jack Lemmon falling for Shirley MacLaine while work uses his apartment for trysts.

4 more great rom-coms from the 1960s: Breakfast at Tiffany’s, Barefoot in the Park, Funny Girl, My Night at Maud’s.

1970s rom-com: Harold and Maud

Harold is a 19-year-old so obsessed with death that he drives a hearse, stages fake suicides, and attends the funerals of people he doesn’t know. While doing the latter, he meets Maude, a 79-year-old whose lust for life finds her frequently breaking the law, and always having a good time. This odd couple forms an immediate bond, and Maude’s optimism starts to rub off on Harold, just as their friendship turns into an unconventional romance.

Harold and Maud is another dark rom-com, in line with the challenging cinema “New Hollywood” was producing throughout the 1970s. Colin Higgins’ script started out as his film school thesis, and while the film flopped at the time, a cult has steadily built around it ever since, so-much-so that it was selected for preservation by the National Film Registry, and voted 45th funniest film of all-time by the American Film Institute.

Runner-Up: The Goodbye Girl

Neil Simon writes and Richard Dreyfuss stars in this touching tale of a struggling actor falling for a single mother.

4 more great rom-coms from the 1970s: Annie Hall, Grease, The Heartbreak Kid, What’s Up, Doc?.

1980s rom-com: When Harry Met Sally…

“Can two friends sleep together and love each other in the morning?” That’s the tagline on the When Harry Met Sally… poster, and the question at the heart of the movie. Harry meets Sally in 1977 when the pair drive from Chicago to New York, and they argue most of the way. They meet again – by chance – on a plane in 1982, and it goes just as badly. Then again in a bookstore 1987, but this time a friendship blossoms. Then Harry and Sally have sex, resulting in the audience – maybe – getting an answer to that question.

Nora Ephron’s brilliant script for When Harry Met Sally… defies convention and cliche at every turn, so-much-so that come the climax, you really aren’t sure how the central love-hate relationship will end. Harry is obnoxious and annoying for most of the movie, but as played by Billy Crystal, you can’t help but love him, while Meg Ryan is simply adorable as Sally. Though just as important to the movie working is Bruno Kirby and Carrie Fisher as their hilarious best friends.

Runner-Up: Bull Durham

Bull Durham appears on sports movie lists, but baseball is pretty much forgotten in the film’s second half, which is all about Kevin Costner and Susan Sarandon falling in love.

4 more great rom-coms from the 1980s: Gregory’s Girl, Say Anything, Broadcast News, Moonstruck.

1990s rom-com: Groundhog Day

Cantankerous TV weatherman Phil Connors heads to Punxsutawney in Pennsylvania to broadcast from the annual Groundhog Day celebrations. He has a miserable time, goes to bed, then wakes up on exactly the same day. Phil is stuck in a time-loop, with no obvious means of escape. He uses the opportunity to have fun, break laws, and sleep with lots of women. Along the way, he falls for producer Rita, though try as he might, he can’t convince Rita to love him back.

Groundhog Day is not without problems – Phil using his powers to manipulate women into bed being the main one – but the lesson at the heart of the film softens that blow, with Phil unable to trick Rita into love. Bill Murray has never been better, and his performance makes this maybe the funniest rom-com on this list.

Runner-Up: Jerry Maguire

Jerry Maguire seems to be about a sports agent suffering an early mid-life crisis, but it’s really about him finding love.

4 more great rom-coms from the 1990s: Four Weddings and a Funeral, Clueless, The Wedding Singer, 10 Things I Hate About You.

2000s rom-com: Shaun of the Dead

Shaun of the Dead takes the rom-com and adds zom to the equation. That’s because it’s a romantic-comedy that just happens to play out during the zombie apocalypse. The title character gets dumped by girlfriend Liz for being a slacker, so goes and gets drunk with his mate Ed. Next morning, an army of the undead rise, and Shaun springs into action, endeavouring to save Liz’s life, while at the same time trying to win her back.

Shaun of the Dead is pretty much a perfect film, with Edgar Wright directing the hell out of the script he wrote with Simon Pegg, and Pegg’s onscreen partnership with Nick Frost proving to be one of cinema’s greatest double acts. The jokes are funny and the horror gory, but what really elevates this one is the love story between Shaun and Liz, and the equally affecting bromance between Shaun and Ed.

Runner-Up: The 40-Year-Old Virgin

This isn’t the most romantic film on our list, but thanks to Steve Carell’s hilarious central performance, it might be the funniest.

4 more great rom-coms from the 2000s: Bridget Jones’s Diary, My Big Fat Greek Wedding, Amélie, Forgetting Sarah Marshall.

2010s rom-com: Sing Street

Set in Dublin in 1985, Sing Street revolves around Conor, whose Dad moves him from his posh school to the Christian Brothers in order to save money. The change doesn’t go well for Conor, as he finds himself bullied by both the boys, and the principal. Then he meets the beautiful Raphina, and Conor suddenly has a purpose in life – to win her heart, by forming a band to impress the aspiring model. After a few false starts, the group find their look and sound and get pretty good, even if the course of love does not run smooth between artist and muse.

A modest hit when released in 2016, Sing Street deserves to be seen by more people. That’s because while it might be about kids, the themes in writer-director John Carney’s script are universal. The songs – by former Danny Wilson frontman Gary Clark – are spectacular. And the ending is as glorious and uplifting as rom-coms get.

Runner- Up: The Big Sick

There’s some tragedy mixed with the comedy and romance in this one, a largely autobiographical film about Kumail Nanjani and Emily V. Gordon’s real-life relationship.

4 more great rom-coms from the 2010s: Crazy Stupid Love, Crazy Rich Asians, Long Shot, Love Simon.

2020s rom-com: Rye Lane

Rye Lane came seemingly out of nowhere to charm the pants off audiences all over in 2023. Set in Peckham, the film plays like a South London version of Before Sunrise, as boy and girl meet by chance, then spend the rest of the day together.

Featuring star-making turns from David Jonnson and Vivian Oparah as the potential couple in question, Rye Lane follows typical rom-com conventions. But the jokes are laugh-out-loud funny, and the performances charming across the board. While it’s nice to see romance play out in a colorful location rarely seen onscreen.

Runner-Up: Palm Springs

Groundhog Day with a sci-fi twist, Palm Springs sees Andy Samberg stuck in a time-loop in the titular location, and Cristin Milioti as the woman he slowly falls in love with.

4 more great rom-comes from the 2020s: Emma, The Photograph, Happiest Season, Spontaneous.

So those are our picks for the the best rom-coms of all time. And if you like a list, check out our feature on the top-grossing movies of all-time, including rom (but definitely not com) Titanic.