Our problems may not amount to a hill of beans in this world, but at least we can always count on good romantic comedies to keep things light.
So for goodness sake, stop with the doomscrolling and enjoy the ensuing list of various duos making fools of themselves for love, and most important of all, making us laugh in the process.
1. Bringing Up Baby (1938)
Howard Hawks returns for the top entry on this list, proving that sheer silliness can be deeply entertaining, so much so that leads Katharine Hepburn and Cary Grant delayed filming because even they couldn’t resist the laughing fits which constantly overtook them. Grant plays the constantly befuddled paleontologist David Huxley, all set up to enter a loveless marriage and awaiting a final piece of a brontosaurus skeleton for the museum he’s also trying to secure a hefty donation for.
Then Hepburn’s flighty heiress Susan Vance enters his well-ordered world with all the force of a hurricane, quickly disrupting his engagement, losing his bone, and generally disrupting his life, with some help via her pet leopard Baby. Chances are you won’t be able to hold in the laughter either, as Hepburn and Grant prove that a perfect duo can sell every zanily absurdist turn the movie takes.
2. Gentlemen Prefer Blondes (1953)
How iconic is the Howard Hawks masterpiece Gentlemen Prefer Blondes? Let me count the ways. Or perhaps I’ll just let Marilyn Monroe’s supposedly ditzy showgirl take the stage as Lorelei, with her brunette bestie and fellow entertainer Jane Russell providing the sarcastically witty barbs as Dorothy.
The two certainly find plenty to do as they board a ship en route to their next performance in Paris, with the disapproving father of Lorelei’s fiancé hiring a private detective to shadow them as a diamond tiara goes missing. It’s also forever a showcase for Monroe’s exquisite comedic skills, and of course, who could forget her rendition of “Diamonds Are A Girl’s Best Friend,” which became a point of reference in the decades since.
3. The Lady Eve (1941)
Humor doesn’t get much more wicked than in this screwball romp. Roger Ebert himself proclaimed, “If I were asked to name the single scene in all of romantic comedy that was sexiest and funniest at the same time, I would advise beginning at six seconds past the 20-minute mark in Preston Sturges’ The Lady Eve. Barbara Stanwyck is at her wily best as Jean, a card shark who ends up falling for her mark, the naive, hopelessly clumsy brewing heir Charles Pike (Henry Fonda).
As the duo comes together and falls apart on repeat, the constant thread is the movie’s shrewdly funny observations on class, wealth, and status, with Jean effortlessly charming her way into society’s upper crust through sheer daring and charisma. Yes, it’s definitely the same dame.
4. Clueless (1995)
Jane Austen makes a second appearance on this list for the previously mentioned Amy Heckerling’s reworking of Emma, with Alicia Silverstone standing in for the novel’s titular socialite as Cher, a wealthy and popular Beverly Hills teen queen. Cher also sees herself a matchmaker who knows better than peers and teachers alike, only to discover otherwise once she has to face the consequences for her less well thought out choices.
A satire that skillfully and humorously channels the spirit of Austen in a modern setting while respecting its characters, it also features a young Paul Rudd as Mr. Knightley stand-in Josh, and the late great Brittany Murphy in one of her first roles.
5. The Shop Around the Corner (1940)
In a genre that practically owes its existence to the enemies to lovers trope, The Shop Around the Corner stands out. Klara Novak (Margaret Sullavan) and Alfred Kralik (James Stewart) are already in love when the movie kicks off, unbeknownst to themselves, having already formed a connection through a series of sweetly passionate anonymous pen pal letters.
But in the meantime, they’re bickering rivals at the Budapest shop where they’re both employed, exchanging the kind of barbs that would make Nora Ephron proud. Their first date in a cafe (with only one of them aware it is a date) is one of the all-time great movie scenes, with director Ernst Lubitsch bringing his singular, trademark humor in the most well-known example of what came to be known as “The Lubitsch Touch.”
6. Ninotchka (1939)
When you have Billy Wilder as a co-writer and Ernst Lubitsch as a director, the end result is bound to be a laugh riot. The screenplay crackles with wit as it tells the tale of two people on the opposing sides of an ideological war who fall passionately in love.
Greta Garbo playfully sends up her own somber star image as the eponymous Ninotchka, a Soviet official who arrives in Paris to oversee a jewels sale meant to boost the Russian economy, only to succumb to the charms of Leon (Melvyn Douglas), who is attempting to recover them on behalf of their previous owner, a member of the former Russian aristocracy. The oddly tender love story that follows is also a satire of communism, authoritarianism, and a kind of modern fairy tale in which two people find their own happy ending despite the unstoppable forces of history itself.
7. When Harry Met Sally… (1989)
“I’ll have what she’s having.” We all would, wouldn’t we, as Harry and Sally meet, despise each other, meet years later, despise each other again, then finally warm up to each other ten years after their first encounter. They become friends and try to keep it that way, despite the tension and growing evidence that they’re perfect for each other.
Director Rob Reiner and writer Nora Ephron are a match made in romcom heaven as they give us what would become a beloved classic, including the much missed Carrie Fisher as Sally’s best friend and confidante who has her own romantic troubles, but eventually finds a happily ever after of her own.
8. Ball of Fire (1941)
Billy Wilder makes a second appearance on this list, this time as co-writer of the screwball comedy Ball of Fire, which follows the madcap adventures which ensue after wisecracking nightclub singer Sugarpuss O’Shea (Barbara Stanwyck) is taken in by a group of professors working on an encyclopedia. Unbeknownst to them, she’s actually on the run from the police, who are looking to question her in connection with her mob lover Joe Lilac (Dana Andrews).
Things get complicated when the young Professor Bertram Potts (Gary Cooper) begins to fall for their guest, with the rest of his cohorts also bonding with Sugarpuss as she literally brightens up the stuffy mansion where they conduct their research. The result is the funniest, and cleverest, reworking of Snow White and the Seven Dwarfs ever made.
9. A New Leaf (1971)
Elaine May is known for intelligently interrogating cinematic tropes through character, and A New Leaf is no exception. It’s difficult to imagine a more unlikely romantic hero than Walter Matthau’s Henry Graham, a self-absorbed, wealthy playboy who’s startled to discover that he’s burned through his entire inheritance.
Finding himself broke and sans any actual skills, he decides to marry into money, then do away with his bride so he can continue to live as he pleases. He believes he’s found the perfect victim in Henrietta (Elaine May) who’s rich, socially inept, perfectly clumsy, and without any family. Graham quickly wins her over, only to find himself touched by the sincerity of his wife’s affection for him, and May proves to have a gift for physical comedy that also helps build sympathy for Graham as he very satisfyingly finds himself on the receiving end of her ineptitude. It’s difficult to imagine a couple more oddly well-matched for each other.
10. But I’m A Cheerleader (1999)
How do you make conversion camp not only funny, but deeply romantic? If you’re Jamie Babbit, you cast Natasha Lyonne as Megan, a naive girl who’s shipped off to ‘rehab’ when her straitlaced family and friends conclude, rightly, that Megan is a lesbian.
Once she arrives, she not only acknowledges the truth about herself, she quickly falls for the rebellious Graham (Clea DuVall) whose bad girl exterior can’t help but soften as the two grow closer. Babbit not only hilariously takes aim at heteronormativity, she adorns her picture with dizzying bursts of bright pinks and blues, and a supporting cast that includes RuPaul, Melanie Lynskey, Cathy Moriarty, and Julie Delpy. And Megan’s final romantic gesture that combines her love of cheerleading and Graham is one of the sweetest, satisfying cinematic send-offs ever.
11. It Happened One Night (1934)
Before Roman Holiday, there was another story of a privileged woman gone rogue and the reporter with a secret heart of gold who crosses her path. When spoiled, sheltered heiress Ellie Andrews (Claudette Colbert) literally jumps ship in an effort to rejoin the man she impulsively married, she crosses paths with Peter Warne (Clark Gable), who agrees to assist her in exchange for an exclusive story.
As the two make their way across America by various means in a country in the grip of the Depression, the two unsurprisingly form a connection that is more shocking for remaining as funny and memorable nearly a century later.
12. The Apartment (1960)
Trust Billy Wilder to mine comedic gold out of a premise that involves lowly NYC insurance worker C.C. Baxter (Jack Lemmon) lending his apartment to company executives for their extramarital affairs in the hopes of a quicker rise to the top.
Needless to say, it doesn’t quite work out that way, especially when he discovers that Fran (Shirley MacLaine) the elevator operator he’s interested in himself, is the mistress of his smarmy boss (Fred MacMurray). When complications inevitably occur, what could’ve been a dark depiction of an uncaring world becomes a deeply funny journey of two flawed but ultimately good-hearted people discovering their true worth.
13. Fire Island (2022)
A retelling of Jane Austen’s Pride and Prejudice set in the modern world and centered around a tight-knit found family which mostly consists of queer men of Asian descent? Faster than you can say yes please, the ensemble of Fire Island effortlessly and joyously dance their way into our hearts as the guys gather for a weeklong getaway at the titular location.
Before long our Elizabeth Bennet stand-in Noah (Joel Kim Booster) has found his Mr. Darcy in Will (Conrad Ricamora), and sparks fly as enemies make their way to lovers. Noah’s one-liners, and the movie’s criticism of the classism and racism of our day would likely make Austen proud.
14. Moonstruck (1987)
“I lost my hand! I lost my bride!” It’s one of the more iconic Nicolas Cage moments in a career that’s practically built on them, and you can count on Cage to lean into the deranged romanticism of it all to make us root for Ronny Cammareri to seduce Cher’s Loretta Castorini away from her boorish fiance. Who is also Ronny’s brother.
Meanwhile, Loretta’s parents are having their own issues, and their circle of supporting friends and family are characters in themselves. But it’s Ronny and Loretta who make us swoon and laugh in equal measure in what is now a very vintage portrayal of Brooklyn.
15. Look Who’s Talking (1989)
Adorable talking babies are an easy shortcut to humor, but Amy Heckerling gives us one of the more unique contributions to the genre seven years after Fast Times at Ridgemont High, and a mere six years before Clueless would burst onto the scene (scroll down and you’ll also find it near the top of the list).
Kirstie Alley is a thirtysomething accountant making all the wrong choices in her love life, finding herself pregnant and abandoned by her married lover – and client – Albert. But she finds a new prospect right as she’s about to give birth in the childish but kind-hearted taxi driver James (John Travolta), who rushes her to the hospital just in time to witness her son Mikey being born. Humorously voiced in and out of the womb by Bruce Willis, seeing the world through his eyes is a riot. And then there’s Olympia Dukakis as Alley’s mother, who gives all the good advice with reliably fantastic delivery.
16. Roman Holiday (1953)
How can we count the innumerable ways William Wyler’s film is one of his most winning in a career built upon them? It’s hilarious, it takes place in gorgeous black and white in an equally stunning setting, and it introduced the world to Audrey Hepburn as the European princess Ann, who is infantilized and stifled by her sheltered world and routines.
When she escapes from her guardians, she quickly cuts her hair into what would become Hepburn’s iconic bob, and bonds with Joe Bradley (Gregory Peck), who is secretly a reporter looking to write an exclusive scoop on the princess. Romance soon complicates things, and the humor sparkles with the wit and chemistry of its leads.
17. I Love You Phillip Morris (2009)
This one is based on the true story of Steven Russell (Jim Carrey), who was a cop, a con man, and very much in love with Phillip Morris (Ewan McGregor), who he met in prison. As the movie tells it, it’s difficult to really feel sorry for the men Russell gleefully embezzled from, even as the lies mount up as sure as the laughs.
It’s certainly easy to grin as Carrey runs circles around these guys until he’s caught, and it’s easy to sympathize with him since the only thing that’s really genuine is his love for the sweetly sincere McGregor. There’s also Leslie Mann, who makes the most of her small role as Russell’s ex-wife Debbie.
18. The Holiday (2006)
Another standout from the early 2000s, The Holiday was mostly dismissed as predictable “chick flick” fare at the time of its release, only to later gain appreciation as a modern holiday viewing staple. British writer Iris (Kate Winslet) and LA movie trailer producer Amanda (Cameron Diaz) decide to swap homes for the holidays, each meeting with a love interest that sparks them to change up their lives for the better.
Jude Law packs on so much charm it should be illegal, while Jack Black plays against type as a vulnerable composer. There’s also Hollywood legend Eli Wallach to dispense wisdom and commentary on the state of movies, with writer-director Nancy Meyers ensuring the laughs land in lavishly cozy surroundings.
19. Bridesmaids (2011)
Romcoms were at something of a low point in the early aughts, with the genre disdainfully dismissed as spitting out critically panned movies whose guilty pleasures were reserved for (white) women only. But that changed when Bridesmaids won over audiences and critics, proving that an all-female cast could make money while bringing the laughs.
It was also a pioneer in the way female friendships dominated, with Annie’s (Kristen Wiig) insecurity over her lifelong BFF Lillian (Maya Rudolph) causing much of the mayhem as she struggles with her duties as maid of honor. It may drive Annie to her lowest point yet, but she also bonds with a sweetly winning Chris O’Dowd and helps Melissa McCarthy achieve new career heights on the way to her own happy ending.
20. My Big Fat Greek Wedding (2002)
Nia Vardalos struck comedy gold with this one, writing and starring as Toula, the lovelorn daughter of a large, boisterous Greek family who decides to give herself a makeover inside and out, complete with glow up and college course, just in time for her crush Ian (John Corbett at his most dreamy) to stroll back into her life.
But the real obstacles come in the form of Toula’s loving family, dismayed that she’s fallen not only for a non-Greek, but (gasp!) a WASP. Thankfully, the humor flows from the way the clan opens up to accept Ian, and Toula gets to have it all: the hot guy, the nice wedding, and the loving support of her community. And the third film opens in theaters in the fall.
Honorable mentions: 10 Things I Hate About You, The Big Sick, Always Be My Maybe, Bros, Eternal Sunshine of the Spotless Mind, Isn’t It Romantic, LA Story, Some Like It Hot, His Girl Friday, Down With Love, How to Lose A Guy in 10 Days, D.E.B.S., One Fine Day, The Princess Bride.
Andrea Thompson is a writer, editor, and film critic who is also the founder and director of the Film Girl Film Festival.
She is a member of the Chicago Indie Critics and runs her own site, A Reel Of One’s Own, and has written for RogerEbert.com, The Spool, The Mary Sue, Inverse, and The Chicago Reader. She has no intention of becoming any less obsessed with cinema, comics, or nerdom in general.
