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Paste's The 100 Best Romantic Comedies of All Time

100 films Ranked Updated 3 days ago
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The Philadelphia Story
George Cukor 1940 1h 53m 7.8

The Philadelphia Story is a comedy starring Cary Grant, Katherine Hepburn. Tracy Lord is idolised by everybody and must keep her sinister ex-husband, an alcoholic reporter, and her future clean-record husband happy.

The Princess Bride
Rob Reiner 1987 1h 39m 7.8

Characters come to life from a classic fairy tale book read by a grandfather to his grandson.

When Harry Met Sally...
Rob Reiner 1989 1h 36m 7.8

When Harry Met Sally is a relationship comedy from the early 90’s that became a cult classic. Most famous is the scene in which Sally performs a fake orgasm in a crowded restaurant to prove that girls fake it sometimes.

Annie Hall
Woody Allen 1977 1h 33m 8.1

The neurotic New Yorker Woody Allen tells one of the greatest romantic comedies to be set in the city of New York.

Roman Holiday
William Wyler 1953 1h 59m 7.9

Roman Holiday is a romantic comedy starring Audrey Hepburn and Gregory Peck involving a mix-up game with a young and beautiful princess who spends some days with the charming American reporter in Rome.

It Happened One Night
Frank Capra 1934 1h 45m 8.0

Comic romance between a down-to-earth newspaper reporter and a spoiled runaway heiress.

Le fabuleux destin d'Amélie Poulain
Jean-Pierre Jeunet 2001 2h 2m 8.6

At a tiny Parisian café, the adorable yet painfully shy Amélie accidentally discovers a gift for helping others. Soon Amelie is spending her days as a matchmaker, guardian angel, and all-around do-gooder. But when she bumps into a handsome stranger, will she find the courage to become the star of her very own love story?

His Girl Friday
Howard Hawks 1940 1h 32m 7.9

Walter Burns is an irresistibly conniving newspaper publisher desperate to woo back his paper’s star reporter, who also happens to be his estranged wife. She’s threatening to quit and settle down with a new beau, but, as Walter knows, she has a weakness: she can’t resist a juicy scoop.

Some Like It Hot
Billy Wilder 1959 2h 3m 8.8

PLEASE DELETE, EXISTS ALREADY!

Groundhog Day
Harold Ramis 1993 1h 41m 8.3

A comedy about an egocentric and sinister television weather reporter with a bad case of Deja-Vu. The weather reporter, Bill Murray, is sent to the famous Groundhog Day tradition in the small town of Punxsutawney were he unwillingly has to report on a little more than he expected. Let's just say he had to do a few retakes of the report.

Trouble in Paradise
Ernst Lubitsch 1932 1h 23m 8.0

Trouble in Paradise is one of the most important films of Actor, Producer, and Director Ernst Lubitisch, and his personal favorite of all the films he’s made. A story of two thieves who fall in love and begin doing jobs together under the employment of a beautiful woman who stirs up the relationship.

Eternal Sunshine of the Spotless Mind
Michel Gondry 2004 1h 48m 8.8

What would happen if we could erase the worst experiences and relationships from our memory. Charlie Kaufman and Michel Gondry combined forces to answer this very question.

Bringing Up Baby
Howard Hawks 1938 1h 42m 8.1

Bringing Up Baby is an American screwball comedy starring Cary Grant and Katherine Hepburn.

The Lady Eve
Preston Sturges 1941 1h 37m 7.9

Returning from a year up the Amazon studying snakes, the rich but unsophisticated Charles Pike meets con-artist Jean Harrington on a ship. They fall in love, but a misunderstanding causes them to split on bad terms. To get back at him, Jean disguises herself as an English lady, and comes back to tease and torment him.

Sabrina
15.

Sabrina

Billy Wilder 1954 1h 54m 7.8

After her return from school in Paris, a playboy finally takes notice of his family's chauffeur's daughter, who's long had a crush on him, but he questions his more serious brother's motives when he warns against getting involved with her.

City Lights
Charlie Chaplin 1931 1h 27m 8.5

City Lights is the first silent film that Charlie Chaplin directed after he established himself with sound accompanied films. The film is about a penniless man who falls in love with a flower girl. The film was a great success and today is deemed a cult classic.

Moonrise Kingdom
Wes Anderson 2012 1h 34m 8.0

Set in the 1960s, a pair of young lovers flee their New England island town, prompting a local search party led by the Sheriff (Willis) and the girl's parents (Murray, McDormand) to fan out to find them.

Singin' in the Rain
Stanley Donen, Gene Kelly 1952 1h 43m 8.6

Hollywood's attempts to move from the 'silent' era to the 'Talkies' are not going as planned.

The Apartment
Billy Wilder 1960 2h 6m 8.6

The Apartment came out shortly after the success of ‘Some Like it Hot’ from director Billy Wilder and thus making it the most successful films of the year. Full of trivialities this comedy is a harsh critic of coporate world and the American way of life.

Pretty Woman
Garry Marshall 1990 2h 7.1

A modern day fairy tale of a big city prostitute who becomes a princess after a rich man falls in love with her. The film made Julia Roberts a superstar in the 1990’s.

The Shop Around the Corner
Ernst Lubitsch 1940 1h 39m 7.9

Two employees at a gift shop can barely stand one another, without realising that they are falling in love through the post as each other's anonymous pen pal.

L.A. Story
Mick Jackson 1991 1h 35m 7.2

With the help of a talking freeway billboard, a "wacky weatherman" tries to win the heart of an English newspaper reporter, who is struggling to make sense of the strange world of early-90s Los Angeles.

Harold and Maude
Hal Ashby 1971 1h 32m 8.5

A deadpan young man obsessed with death meets an eccentric septuagenarian who teaches him to live life to the fullest.

The 40 Year Old Virgin
Judd Apatow 2005 1h 56m 6.8

Andy at the age of 40 still hasn't had sex. He lets his secret slip at a poker game with his buds from work. After the revealing all his friends are on a mission to help get him laid. Along the way Andy meets a nice mom: Trish who fall head over heels for each other.

Love & Basketball
Gina Prince-Bythewood 2000 2h 5m 5.0

In 1981 in L.A., Monica moves in next door to Quincy. They're 11, and both want to play in the NBA, just like Quincy's dad. Their love-hate relationship lasts into high school, with Monica's edge and Quincy's top-dog attitude separating them, except when Quincy's parents argue and he climbs through Monica's window to sleep on the floor.

Punch-Drunk Love
Paul Thomas Anderson 2002 1h 36m 7.1

A beleaguered small-business owner gets a harmonium and embarks on a romantic journey with a mysterious woman.

The Goodbye Girl
Herbert Ross 1977 1h 51m 8.0

After being dumped by her live-in boyfriend, an unemployed dancer and her 10-year-old daughter are reluctantly forced to live with a struggling off-Broadway actor.

Knocked Up
Judd Apatow 2007 2h 9m 7.1

For fun loving party animal Ben Stone, the last thing he ever expected was for his one night stand to show up on his doorstep eight weeks later to tell him she's pregnant.

Bridget Jones's Diary
Sharon Maguire 2001 1h 37m 6.9

Bridget Jone’s Diary is a romantic love story comedy from the best selling novel of the same name by Helen Fielding. A chaotic Jones meets a snobbish lawer named Marc and soon he enters into her world of imperfections.

Clueless
30.

Clueless

Amy Heckerling 1995 1h 37m 6.7

Cher, a high school student in Beverly Hills, must survive the ups and downs of adolescent life. Her external demeanor at first seems superficial, but rather it hides her wit, charm, and intelligence which help her to deal with relationships, friends, family, school, and the all-important teenage social life.

Four Weddings and a Funeral
Mike Newell 1994 1h 57m 7.2

Four Weddings And A Funeral is a British comedy about a British Man named Charles and an American Woman named Carrie who go through numerous weddings before they determine if they are right for one another.

She's Gotta Have It
1986 1h 24m

The story of Nola Darling's simultaneous sexual relationships with three different men is told by her and by her partners and other friends. All three men wanted her to commit solely to them; Nola resists being "owned" by a single partner.

Born Yesterday
George Cukor 1950 1h 43m 7.0

Uncouth, loud-mouth junkyard tycoon Harry Brock descends upon Washington D.C. to buy himself a congressman or two, bringing with him his mistress, ex-showgirl Billie Dawn.

A Matter of Life and Death
Michael Powell, Emeric Pressburger 1946 1h 44m 8.7

When a young airman miraculously survives bailing out of his aeroplane without a parachute, he falls in love with an American radio operator. But the officials in the other world realise their mistake, and despatch an angel to collect him.

Coming to America
John Landis 1988 1h 57m 6.8

An African prince goes to Queens, New York City to find a wife whom he can respect for her intelligence and will.

Adam's Rib
George Cukor 1949 1h 41m 8.6

Spencer Tracy and Katharine Hepburn play Adam and Amanda Bonner, a husband-and-wife attorney team, both drawn to a case of attempted murder.

The Big Sick
Michael Showalter 2017 2h 8.0

Pakistan-born comedian Kumail Nanjiani and grad student Emily Gardner fall in love but struggle as their cultures clash. When Emily contracts a mysterious illness, Kumail finds himself forced to face her feisty parents, his family's expectations, and his true feelings.

Ninotchka
38.

Ninotchka

Ernst Lubitsch 1939 1h 50m 8.4

A stern Russian woman sent to Paris on official business finds herself attracted to a man who represents everything she is supposed to detest.

Sleeping with Other People
Leslye Headland 2015 1h 40m 5.5

A good-natured womanizer and a serial cheater form a platonic relationship that helps reform them in ways, while a mutual attraction sets in.

Sing Street
John Carney 2016 1h 45m 7.5

A boy growing up in Dublin during the 1980s escapes his strained family life by starting a band to impress the mysterious girl he likes.

The Prizefighter and the Lady
1933 1h 42m

An ex-sailor turned boxer finds romance and gets a shot at the heavyweight title.

A Room with a View
James Ivory 1985 1h 57m 8.2
WALL•E
43.

WALL•E

Andrew Stanton 2008 1h 38m 8.6

After hundreds of years doing what he was built for, WALL•E— a robot designed to clean up the earth—discovers a new purpose in life when he meets a sleek search robot named EVE. EVE comes to realize that WALL•E has inadvertently stumbled upon the key to the planet's future, and races back to space to report to the humans. Meanwhile, WALL•E chase...

How to Marry a Millionaire
Jean Negulesco 1953 1h 36m 7.0

Three women set out to find eligible millionaires to marry, but find true love in the process.

There's Something About Mary
Peter Farrelly, Bobby Farrelly 1998 2h 7.3

Having never fully recovered from a prom date that became a total disaster, a man finally gets a chance to reunite with his old prom date, only to run up against other suitors including the sleazy detective he hired to find her.

Enchanted
46.

Enchanted

Kevin Lima 2007 1h 47m 7.1

Giselle is forced from her 2D-animated world of Andalasia into real-life New York City by an evil witch.

Silver Linings Playbook
David O. Russell 2012 2h 2m 7.4

After losing his job and wife, and spending time in an institution, a former teacher winds up living with his parents. He wants to rebuild his life and reconcile with his wife, but his father would be happy if he shared his obsession with the Philadelphia Eagles. Things get complicated when he meets Tiffany Maxwell who offers to help him reconne...

The Purple Rose of Cairo
Woody Allen 1985 1h 22m 8.2

Cecilia is a waitress in New Jersey, living a dreary life during the Great Depression. Her only escape from her mudane reality is the movie theatre. After losing her job, Cecilia goes to see 'The Purple Rose of Cairo' in hopes of raising her spirits, where she watches dashing archaeologist Tom Baxter time and again.

Juno
49.

Juno

Jason Reitman 2007 1h 36m 7.9

A young girl named Juno gets herself pregnant and tries to stand on her own. She soon learns a few lessons about being grown up.

Sleepless in Seattle
Nora Ephron 1993 1h 45m 6.8

A young boy who tries to set his dad up on a date after the death of his mother. He calls into a radio station to talk about his dad’s loneliness which soon leads the dad into meeting a Journalist Annie who flies to Seattle to write a story about the boy and his dad. Yet Annie ends up with more than just a story in this popular romantic comedy.

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