The 20 Funniest Romantic Comedies of All Time

His Girl Friday
The story involves something about a second marriage and a subplot in which an escaped prisoner hiding in a desk, but it doesn’t matter – the real focus of ‘His Girl Friday’ is the wonderful, charming, fast-talking chemistry between Rosalind Russell and Cary Grant.
The Philadelphia Story
One of the best rom coms ever written, 'The Philadephia Story' sees Jimmy Stewart and Cary Grant competing for the affections of Katherine Hepburn, and the mayhem that ensues. But really, who could blame them?
Bringing Up Baby
In this screwball comedy, Katherine Hepburn proves that she can be just as charming as a flaky heiress as she can a fast-talking dame, while Cary Grant proves that he has electric chemistry with everyone... even a jungle cat.
It Happened One Night
The first classic of the genre, ‘It Happened One Night’ is a hilarious adventure between socialite Ellie and newspaper man Peter, who care for each other as much as they drive each other crazy. Yes, he loves her, but don’t hold it against him.
The Apartment
'The Apartment' might be best known for its closing lines, but everything that comes before is just as funny and bittersweet thanks to the incredible chemistry and iconic performances of Jack Lemmon and Shirley MacLaine.
Harold and Maude
The nontraditional, darkly funny love story centers on an elderly woman determined to live life to the fullest and a young man obsessed with death, who happen to meet at a funeral they’re both crashing. The ‘70s were weird.
Annie Hall
Though Woody Allen's made a great deal of great films since, he'll probably never beat his 1977 classic. Funny, bittersweet, and anchored by a star-making performance from Diane Keaton.
Moonstruck
There was a time and place when Nicolas Cage was a genuine rom com hero, and it was 1987, opposite Cher's Oscar-winning performance. Although, not even he could outshine the wailing, constantly about-to-die Sicilian mother.
The Princess Bride
A gorgeous, epic fairy tale about love, revenge, sword fights, giants, pirates, magic and some of the best one-liners ever put on screen. By the end, you might not even mind the kissing so much.
When Harry Met Sally...
Arguably one of the greatest rom coms ever made, 'When Harry Met Sally' has everything: a witty leading lady, a charming guy-next-door type, a smart, funny script and fake orgasms in a diner. What more could you want from a movie?
Bridget Jones's Diary
Forget the other Mr. Darcy; Colin Firth was never dreamier than he was in 'Bridget Jones' Diary.' Come on, "I like you very much, just as you are?" Rom com gold.
Clueless
This reworking of Jane Austen’s ‘Emma’ gave us so many gifts: Alicia Silverstone’s hair, styling tips for plaid skirts, Paul Rudd as a romantic hero, and the best insult of all time, “You’re a virgin who can’t drive.” Way harsh.
The Wedding Singer
Before he started making the same three films over and over, Adam Sandler wrote this charming, heartwarming, hilarious rom com that proves that true love, airplane serenades and meatballs can overcome anything.
The Best Man
Once upon a time, Taye Diggs and Morris Chestnut were kings of the rom com, and this was their magnum opus, a hilarious, touching, realistic film about best friends coming together for a wedding. And thanks to the sequel, those glory days might be making a comeback.
Roman Holiday
Audrey Hepburn’s breakthrough film is remarkable not just for its refreshingly realistic and moving ending, but also for being the reason that every tourist who arrives in Rome pretends to have their hand bitten off by la Bocca della Verita. Thanks, Gregory Peck.
Pretty in Pink
He might not have ended up with the girl, but Jon Cryer’s Ducky did manage to steal the film with his hilarious, awkward and impassioned performance of Otis Redding’s “Try a Little Tenderness.” Blake who?
Boomerang
Don’t let the phrase “Eddie Murphy rom com” scare you away; ‘Boomerang’ is a hilarious, witty film about a man who learns to treat women properly featuring an A-List cast (Eartha Kitt! Grace Jones!) and some seriously intense chemistry between Murphy and Robin Givens.
The Proposal
Sandra Bullock at her most hilariously uptight and Ryan Reynolds at his most charming couldn't hold a candle to the hysterical, outrageous, scene stealing performance given by Betty White.
Forgetting Sarah Marshall
Buried beneath the puppet shows, full-frontal nudity and Russell Brand, 'Forgetting Sarah Marshall' is a funny, sweet film about learning to move on after a breakup. When people posit Jason Segel as the rom com hero of our time, this is why.
Sleepless in Seattle
Meg Ryan and Tom Hanks are great, sure, but the film’s real triumph is that it has become more closely associated with meeting on top of the Empire State Building than the iconic film that did it first, ‘An Affair to Remember.’

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