My Favorite Romantic Comedies

Only the first 20 are in order. I gave up after that. :P
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1.
Pretty Woman (1990)
    1 2 3 4 5 6 7 8 9 10 7.0/10 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
 
2.
Sweet Home Alabama (2002)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
A young woman who's reinvented herself as a New York socialite must return home to Alabama to obtain a divorce from her husband, after seven years of separation. (108 mins.)
Director: Andy Tennant
 
3.
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
 
4.
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
 
5.
Benny & Joon (1993)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A mentally ill young woman finds her love in an eccentric man who models himself after Buster Keaton. (98 mins.)
 
6.
While You Were Sleeping (1995)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A hopeless romantic Chicago Transit Authority token collector is mistaken for the fiancée of a coma patient. (103 mins.)
Director: Jon Turteltaub
 
7.
Notting Hill (1999)
    1 2 3 4 5 6 7 8 9 10 7.1/10 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
 
8.
Sabrina (1954)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A playboy becomes interested in the daughter of his family's chauffeur, but it's his more serious brother who would be the better man for her. (113 mins.)
Director: Billy Wilder
 
9.
Top Hat (1935)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
An American dancer comes to Britain and falls for a model whom he initially annoyed, but she mistakes him for his goofy producer. (101 mins.)
Director: Mark Sandrich
 
10.
French Kiss (1995)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
A woman flies to France to confront her straying fiancé, but gets into trouble when the charming crook seated next to her uses her for smuggling. (111 mins.)
Director: Lawrence Kasdan
 
11.
It Could Happen to You (1994)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
A police officer promises to share his lottery ticket with a waitress in lieu of a tip. (101 mins.)
Director: Andrew Bergman
 
12.
My Best Friend's Wedding (1997)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
When a woman's long-time friend reveals he's engaged, she realizes she loves him herself and sets out to get him, with only days before the wedding. (105 mins.)
Director: P.J. Hogan
 
13.
The Holiday (2006)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
Two women troubled with guy-problems swap homes in each other's countries, where they each meet a local guy and fall in love. (138 mins.)
Director: Nancy Meyers
 
14.
Pillow Talk (1959)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
A man and a woman who share a party line cannot stand each other, but he has fun romancing her with his voice disguised. (102 mins.)
Director: Michael Gordon
 
15.
Down with Love (2003)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author. (101 mins.)
Director: Peyton Reed
 
16.
(500) Days of Summer (2009)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
An offbeat romantic comedy about a woman who doesn't believe true love exists, and the young man who falls for her. (95 mins.)
Director: Marc Webb
 
17.
Two Weeks Notice (2002)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
A lawyer decides that she's used too much like a nanny by her boss, so she walks out on him. (101 mins.)
Director: Marc Lawrence
 
18.
Prelude to a Kiss (1992)
    1 2 3 4 5 6 7 8 9 10 5.6/10 X  
A couple fall in love despite the girl's pessimistic outlook. As they struggle to come to terms with their relationship... (105 mins.)
Director: Norman René
 
19.
The American President (1995)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Comedy-drama about a widowed U.S. President and a lobbyist who fall in love. It's all above-board, but "politics is perception", and sparks fly anyway. (114 mins.)
Director: Rob Reiner
 
20.
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
 
21.
Serendipity (2001)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A couple search for each other years after the night they first met, fell in love, and separated, convinced that one day they'd end up together. (90 mins.)
Director: Peter Chelsom
 
22.
Bringing Up Baby (1938)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
While trying to secure a $1 million donation for his museum, a befuddled paleontologist is pursued by a flighty and often irritating heiress and her pet leopard, Baby. (102 mins.)
Director: Howard Hawks
 
23.
The Apartment (1960)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
A man tries to rise in his company by letting its executives use his apartment for trysts, but complications and a romance of his own ensue. (125 mins.)
Director: Billy Wilder
 
24.
The Goodbye Girl (1977)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
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. (111 mins.)
Director: Herbert Ross
 
25.
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 agent with the only athlete who stays with him and his former secretary. (139 mins.)
Director: Cameron Crowe
 
26.
Cactus Flower (1969)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A dentist pretends to be married to avoid commitment, but when he falls for his girlfriend and proposes, he must recruit his lovelorn nurse to pose as his wife. (103 mins.)
Director: Gene Saks
 
27.
Just Like Heaven (2005)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A lonely landscape architect falls for the spirit of the beautiful woman who used to live in his new apartment. (95 mins.)
Director: Mark Waters
 
28.
Charade (1963)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
Romance and suspense ensue in Paris as a woman is pursued by several men who want a fortune her murdered husband had stolen. Who can she trust? (113 mins.)
Director: Stanley Donen
 
29.
The Proposal (2009)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A pushy boss forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation to Canada. (108 mins.)
Director: Anne Fletcher
 
30.
What's Up, Doc? (1972)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
The accidental mix-up of four identical plaid overnight bags leads to a series of increasingly wild and wacky situations. (94 mins.)
 
31.
Tootsie (1982)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Michael Dorsey, an unsuccessful actor, disguises himself as a woman in order to get a role on a trashy hospital soap. (116 mins.)
Director: Sydney Pollack
 
32.
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
 
33.
It's Complicated (2009)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
When attending their son's college graduation, a couple reignite the spark in their relationship. But the complicated fact is they're divorced and he's remarried. (120 mins.)
Director: Nancy Meyers
 
34.
Roman Holiday (1953)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A bored and sheltered princess escapes her guardians and falls in love with an American newsman in Rome. (118 mins.)
Director: William Wyler
 
35.
27 Dresses (2008)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
After serving as a bridesmaid 27 times, a young woman wrestles with the idea of standing by her sister's side as her sibling marries the man she's secretly in love with. (111 mins.)
Director: Anne Fletcher
 
36.
Some Like It Hot (1959)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
When two male musicians witness a mob hit, they flee the state in an all-female band disguised as women, but further complications set in. (121 mins.)
Director: Billy Wilder
 
37.
My Big Fat Greek Wedding (2002)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
A young Greek woman falls in love with a non-Greek and struggles to get her family to accept him while she comes to terms with her heritage and cultural identity. (95 mins.)
Director: Joel Zwick
 
38.
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
 
39.
Waitress (2007)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Jenna is a pregnant, unhappily married waitress in the deep south. She meets a newcomer to her town and falls into an unlikely relationship as a last attempt at happiness. (108 mins.)
Director: Adrienne Shelly
 
40.
City Lights (1931)
    1 2 3 4 5 6 7 8 9 10 8.6/10 X  
With the aid of a wealthy erratic tippler, a dewy-eyed tramp who has fallen in love with a sightless flower girl accumulates money to be able to help her medically. (87 mins.)
Director: Charles Chaplin
 
41.
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
 
42.
Mrs. Winterbourne (1996)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Connie Doyle is eighteen and pregnant when her boyfriend kicks her out. She accidentally ends up on... (105 mins.)
“ It's a ripoff of While You Were Sleeping, but I still loved it. ” - ElaineofAstolat
 
43.
America's Sweethearts (2001)
    1 2 3 4 5 6 7 8 9 10 5.7/10 X  
A movie publicist deals with the messy public split of his movie's co-stars while keeping reporters at bay while a reclusive director holds the film's print hostage. (102 mins.)
Director: Joe Roth
 
44.
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
 
45.
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
 
46.
P.S. I Love You (2007)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A young widow discovers that her late husband has left her 10 messages intended to help ease her pain and start a new life. (126 mins.)
 
47.
My Life in Ruins (2009)
    1 2 3 4 5 6 7 8 9 10 5.9/10 X  
A travel guide rediscovers her romantic side on a trip around Greece. (95 mins.)
Director: Donald Petrie
 
48.
New in Town (2009)
    1 2 3 4 5 6 7 8 9 10 5.6/10 X  
A Miami businesswoman adjusts to her new life in a tiny Minnesota town. (97 mins.)
Director: Jonas Elmer
 
49.
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
 
50.
The Wedding Planner (2001)
    1 2 3 4 5 6 7 8 9 10 5.2/10 X  
Mary Fiore is San Francisco's most successful supplier of romance and glamor. She knows all the tricks. She knows all the rules. But then she breaks the most important rule of all: she falls in love with the groom. (103 mins.)
Director: Adam Shankman
 
51.
His Girl Friday (1940)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A newspaper editor uses every trick in the book to keep his ace reporter ex-wife from remarrying. (92 mins.)
Director: Howard Hawks
 
52.
Father Goose (1964)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
During World War II, a man persuaded to live on an isolated island and spot aircraft finds himself responsible for a teacher and several students, all female. (118 mins.)
Director: Ralph Nelson
 
53.
It Happened One Night (1934)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A spoiled heiress running away from her family is helped by a man who is actually a reporter in need of a story. (105 mins.)
Director: Frank Capra
 
54.
Simply Irresistible (1999)
    1 2 3 4 5 6 7 8 9 10 5.3/10 X  
A magical crab works wonders for a terrible chef's culinary skills, leading her towards the man of her dreams. (96 mins.)
Director: Mark Tarlov
 
55.
Blast from the Past (1999)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
A naive man comes out into the world after spending 35 years in a nuclear fallout shelter. (112 mins.)
Director: Hugh Wilson
 
56.
Moonstruck (1987)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
Loretta Castorini, a book keeper from Brooklyn, New York, finds herself in a difficult situation when she falls for the brother of the man she has agreed to marry. (102 mins.)
Director: Norman Jewison
 
57.
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
 
58.
I Married a Witch (1942)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A beautiful 17th-century witch returns to life to plague politician Wallace Wooley, descendant of her persecutor. (77 mins.)
Director: Rene Clair
 
59.
Funny Face (1957)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
An impromptu fashion shoot at a book store brings about a new fashion model discovery in the shop clerk. (103 mins.)
Director: Stanley Donen
 
60.
The Importance of Being Earnest (2002)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
In 1890s London, two friends use the same pseudonym ("Ernest") for their on-the-sly activities. Hilarity ensues. (97 mins.)
Director: Oliver Parker
 
61.
Kate & Leopold (2001)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
An English Duke from 1876 is inadvertedly dragged to modern day New York where he falls for a plucky advertising executive. (118 mins.)
Director: James Mangold
 
62.
Letters to Juliet (2010)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
Sophie dreams of becoming a writer and travels to Verona, Italy where she meets the "Secretaries of Juliet". (105 mins.)
Director: Gary Winick
 
63.
Never Been Kissed (1999)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
A newspaper reporter enrolls in high school as part of research for a story. (107 mins.)
Director: Raja Gosnell
 
64.
Love in the Afternoon (1957)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A middle-aged playboy becomes fascinated by the daughter of a private detective who has been hired to entrap him with the wife of a client. (130 mins.)
Director: Billy Wilder