The Top 50 Romantic Comedies of the last 50 years

These are, I believe the top 50 romantic comedies of the last 50 years. Perhaps there are other movies here and there which could make this list and perhaps the order is debatable but certainly every one of them is deserving of a spot on any list of the 50 best of the last half century.
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1.
When Harry Met Sally... (1989)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Harry and Sally have known each other for years, and are very good friends, but they fear sex would ruin the friendship. (96 mins.)
Director: Rob Reiner
 
2.
The Princess Bride (1987)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
While home sick in bed, a young boy's grandfather reads him a story called The Princess Bride. (98 mins.)
Director: Rob Reiner
 
3.
Notting Hill (1999)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
The life of a simple bookshop owner changes when he meets the most famous film star in the world. (124 mins.)
Director: Roger Michell
 
4.
How to Lose a Guy in 10 Days (2003)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days. Andie Anderson covers the "How To" beat for "Composure" magazine and is assigned to write an article on "How to Lose a Guy in 10 days." They meet in a bar shortly after the bet is made. (116 mins.)
Director: Donald Petrie
 
5.
Sleepless in Seattle (1993)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A recently widowed man's son calls a radio talk-show in an attempt to find his father a partner. (105 mins.)
Director: Nora Ephron
 
6.
Love and Death (1975)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
In czarist Russia, a neurotic soldier and his distant cousin formulate a plot to assassinate Napoleon. (85 mins.)
Director: Woody Allen
 
7.
Love Actually (2003)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
Follows the lives of eight very different couples in dealing with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London, England. (135 mins.)
Director: Richard Curtis
 
8.
There's Something About Mary (1998)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A man gets a chance to meet up with his dream girl from high school, even though his date with her back then was a complete disaster. (119 mins.)
 
9.
Hitch (2005)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
While helping his latest client woo the fine lady of his dreams, a professional "date doctor" finds that his game doesn't quite work on the gossip columnist with whom he's smitten. (118 mins.)
Director: Andy Tennant
 
10.
50 First Dates (2004)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Henry Roth is a man afraid of commitment up until he meets the beautiful Lucy. They hit it off and Henry think he's finally found the girl of his dreams, until he discovers she has short-term memory loss and forgets him the very next day. (99 mins.)
Director: Peter Segal
 
11.
Pretty Woman (1990)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A man in a legal but hurtful business needs an escort for some social events, and hires a beautiful prostitute he meets... only to fall in love. (119 mins.)
Director: Garry Marshall
 
12.
Ella Enchanted (2004)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
Ella is under a spell to be constantly obedient, a fact she must hide from her new step-family in order to protect the prince of the land, her friend for whom she's falling. (96 mins.)
Director: Tommy O'Haver
 
13.
You've Got Mail (1998)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Two business rivals who hate each other in the office fall in love over the Internet. (119 mins.)
Director: Nora Ephron
 
14.
Down with Love (2003)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
Aaaah... it's New York City in 1962, and love is blooming between a journalist and a feminist advice author, who's falling head over heels despite her beau's playboy lifestyle. (101 mins.)
Director: Peyton Reed
 
15.
Anything Else (2003)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
Jerry Falk learns a lesson the hard way when he falls head over heels in love with a beautiful but flighty girl, Amanda. (108 mins.)
Director: Woody Allen
 
16.
The Wedding Singer (1998)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Robbie, a singer, and Julia, a waitress, are both engaged, but to the wrong people. Fortune intervenes to help them discover each other. (95 mins.)
Director: Frank Coraci
 
17.
Bridget Jones's Diary (2001)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A British woman is determined to improve herself while she looks for love in a year in which she keeps a personal diary. (97 mins.)
Director: Sharon Maguire
 
18.
He's Just Not That Into You (2009)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
The Baltimore-set movie of interconnecting story arcs deals with the challenges of reading or misreading human behavior. (129 mins.)
Director: Ken Kwapis
 
19.
Music and Lyrics (2007)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A washed up singer is given a couple days to compose a chart-topping hit for an aspiring teen sensation. Though he's never written a decent lyric in his life, he sparks with an offbeat younger woman with a flair for words. (96 mins.)
Director: Marc Lawrence
 
20.
Play It Again, Sam (1972)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A neurotic film critic obsessed with the movie Casablanca attempts to get over his wife leaving him by dating again with the help of a married couple and his illusory idol, Humphrey Bogart. (85 mins.)
Director: Herbert Ross
 
21.
The Prince and Me (2004)
    1 2 3 4 5 6 7 8 9 10 5.9/10 X  
At college Paige meets Eddie, a fellow student from Denmark, whom she first dislikes but later accepts, likes, and loves; he proves to be Crown Prince Edvard. Paige follows him to Copenhagen, and he follows her back to school with a plan. (111 mins.)
Director: Martha Coolidge
 
22.
Coming to America (1988)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
An African prince goes to Queens, New York City to find a wife whom he can respect for her intelligence and will. (116 mins.)
Director: John Landis
 
23.
Me, Myself & Irene (2000)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A nice-guy cop with dissociative identity disorder must protect a woman on the run from a corrupt ex-boyfriend and his associates. (116 mins.)
 
24.
What Women Want (2000)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
After an accident, a chauvinistic executive gains the ability to hear what women are really thinking. (127 mins.)
Director: Nancy Meyers
 
25.
Kate & Leopold (2001)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
Kate and her actor brother live in N.Y. in the 21st Century. Her ex-boyfriend, Stuart, lives above her apartment... (118 mins.)
Director: James Mangold
 
26.
Annie Hall (1977)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
Neurotic New York comedian Alvy Singer falls in love with the ditzy Annie Hall. (93 mins.)
Director: Woody Allen
 
27.
Ghost (1990)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
After a young man is murdered, his spirit stays behind to warn his lover of impending danger, with the help of a reluctant psychic. (127 mins.)
Director: Jerry Zucker
 
28.
Four Weddings and a Funeral (1994)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
Over the course of five social occasions, a committed bachelor must consider the notion that he may have discovered love. (117 mins.)
Director: Mike Newell
 
29.
Forget Paris (1995)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
Mickey Gordon is a basketball referee who travels to France to bury his father. Ellen Andrews, an American living in Paris... (101 mins.)
Director: Billy Crystal
 
30.
Intolerable Cruelty (2003)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
A beautiful gold digger matches wits with a shrewd Beverly Hills divorce lawyer who is increasingly attracted to her. (100 mins.)
Director: Joel Coen
 
31.
Never Been Kissed (1999)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
A journalist enrolls in her old highschool as part of her research for a story. (107 mins.)
Director: Raja Gosnell
 
32.
13 Going on 30 (2004)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
A girl makes a wish on her 13th birthday and wakes up the next day as a 30-year-old woman. (98 mins.)
Director: Gary Winick
 
33.
Bride & Prejudice (2004)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Jane Austen's Pride and Prejudice gets a Bollywood treatment. (122 mins.)
Director: Gurinder Chadha
 
34.
Runaway Bride (1999)
    1 2 3 4 5 6 7 8 9 10 5.5/10 X  
A reporter is assigned to write a story about a woman who has left a string of fiances at the altar. (116 mins.)
Director: Garry Marshall
 
35.
Moulin Rouge! (2001)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A poet falls for a beautiful courtesan whom a jealous duke covets in this stylish musical, with music drawn from familiar 20th century sources. (127 mins.)
Director: Baz Luhrmann
 
36.
Big (1988)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
When a boy wishes to be big at a magic wish machine, he wakes up the next morning and finds himself in an adult body. (104 mins.)
Director: Penny Marshall
 
37.
Bull Durham (1988)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A fan who has an affair with one minor-league baseball player each season meets an up-and-coming pitcher and the experienced catcher assigned to him. (108 mins.)
Director: Ron Shelton
 
38.
Bridget Jones: The Edge of Reason (2004)
    1 2 3 4 5 6 7 8 9 10 5.9/10 X  
After finding love, Bridget Jones questions if she really has everything she's dreamed of having. (108 mins.)
Director: Beeban Kidron
 
39.
The Music Man (1962)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
Harold Hill poses as a boys' band leader to con naive Iowa townsfolk. (151 mins.)
Director: Morton DaCosta
 
40.
Wimbledon (2004)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
A pro tennis player has lost his ambition and has fallen in rank to 119. Fortunately for him, he meets a young player on the women's circuit who helps him recapture his focus for Wimbledon. (98 mins.)
 
41.
Shallow Hal (2001)
    1 2 3 4 5 6 7 8 9 10 5.9/10 X  
A shallow man falls in love with a 300 pound woman because of her "inner beauty". (114 mins.)
 
42.
Jerry Maguire (1996)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
When a sports agent has a moral epiphany and is fired for expressing it, he decides to put his new philosophy to the test as an independent with the only athlete who stays with him. (139 mins.)
Director: Cameron Crowe
 
43.
Dave (1993)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
To avoid a potentially explosive scandal when the U.S. President goes into a coma, an affable temp agency owner with an uncanny resemblance, is put in his place. (110 mins.)
Director: Ivan Reitman
 
44.
Singin' in the Rain (1952)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
A silent film production company and cast make a difficult transition to sound. (103 mins.)
 
45.
Enchanted (2007)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A princess, who is prepared to be wed, is sent away to New York by an evil queen, where she falls in love with a lawyer. (107 mins.)
Director: Kevin Lima
 
46.
Sex and the City (2008)
    1 2 3 4 5 6 7 8 9 10 5.5/10 X  
A New York writer on sex and love is finally getting married to her Mr. Big. But her three best girlfriends must console her after one of them inadvertently leads Mr. Big to jilt her. (145 mins.)
 
47.
A Funny Thing Happened on the Way to the Forum (1966)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A wily slave must unite a virgin courtesan and his young smitten master to earn his freedom. (99 mins.)
Director: Richard Lester
 
48.
Maid in Manhattan (2002)
    1 2 3 4 5 6 7 8 9 10 5.1/10 X  
A senatorial candidate falls for a hotel maid, thinking she is a socialite when he sees her trying on a wealthy woman's dress. (105 mins.)
Director: Wayne Wang
 
49.
The Bachelor (1999)
    1 2 3 4 5 6 7 8 9 10 5.0/10 X  
A committment-phobic man goes in search of a bride including his fed up girlfriend, to inherit his grandfather's $100 million inheritance. (101 mins.)
Director: Gary Sinyor
 
50.
Bruce Almighty (2003)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A guy who complains about God too often is given almighty powers to teach him how difficult it is to run the world. (101 mins.)
Director: Tom Shadyac