Top 40 Best Romantic Comedies of All Time

This is a list of the 40 must see romantic comedies of all time. The order is certainly debatable, but encompasses several decades of film making.
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1.
An Affair to Remember (1957)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A couple falls in love and agrees to meet in six months at the Empire State Building - but will it happen? (115 mins.)
Director: Leo McCarey
 
2.
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
 
3.
Pride and Prejudice (1995 Mini-Series)
    1 2 3 4 5 6 7 8 9 10 9.0/10 X  
Jane Austen's classic novel about the prejudice that occurred between the 19th century classes and the pride which would keep lovers apart. (327 mins.)
“ By far, the best version of Jane Austen's Pride and Prejudice. Elizabeth Bennett and Mr. Darcy meet and decide that both are horribly suited for one another and take a particular disliking. As time goes on, they come to realize that both were completely wrong about the other. ” - Janet Conway
 
4.
Sense and Sensibility (1995)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
Rich Mr. Dashwood dies, leaving his second wife and her three daughters poor by the rules of inheritance. The two eldest daughters are the titular opposites. (136 mins.)
Director: Ang Lee
“ Rich Mr. Dashwood dies, leaving his second wife and her three daughters poor by the rules of inheritance. The two eldest daughters are the titular opposites. ” - Janet Conway
 
5.
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
 
6.
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
 
7.
The Notebook (2004)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
A poor yet passionate young man falls in love with a rich young woman, giving her a sense of freedom, but they are soon separated because of their social differences. (123 mins.)
Director: Nick Cassavetes
 
8.
Breakfast at Tiffany's (1961)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A young New York socialite becomes interested in a young man who has moved into her apartment building. (115 mins.)
Director: Blake Edwards
“ A kept man becomes friends with a New York party girl in New York City. ” - Janet Conway
 
9.
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
“ A consumate London bachelor only has eyes for one woman, an American he only sees as weddings and funerals. ” - Janet Conway
 
10.
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
“ Jane Austen's Pride and Prejudice gets a Bollywood treatment. ” - Janet Conway
 
11.
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
“ An actress and travel book store owner find romance, but her celebrity situation keeps the romance from ever reaching the next level. ” - Janet Conway
 
12.
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
 
13.
Emma (1996)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
In rural 1800s England things go bad for a young matchmaker after she finds a man for another woman. (120 mins.)
Director: Douglas McGrath
“ A high-brow, yet charming young lady from rural 1800s England, spends her days finding a suitable gentleman for her new friend, only to find her skills as a matchmaker are not as good as she thinks. ” - Janet Conway
 
14.
August Rush (2007)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
A drama with fairy tale elements, where an orphaned musical prodigy uses his gift as a clue to finding his birth parents. (114 mins.)
 
15.
Something New (2006)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Kenya McQueen, an accountant finds love in the most unexpected place when she agrees to go on a blind date with Brian Kelly, a sexy and free-spirited landscaper. (99 mins.)
Director: Sanaa Hamri
 
16.
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
“ The countdown to Christmas and following the love lives of Londoners somehow connected with one another. ” - Janet Conway
 
17.
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
“ A lonely Chicago woman saves the life a man she sees and dreams of every day at the L train, then one day saves his life. His family comes to believe that she's his fiance while he's in a coma. ” - Janet Conway
 
18.
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
“ A New York man tires of complications in relationships, but needs some companionship while working on a big deal in Los Angeles. He finds what he's looking for with a local prostitute with a "heart of gold". ” - Janet Conway
 
19.
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
“ Virginal decorator Doris Day shares a party line with a womanizing songwriter. While she has never met the songwriter, she knows all his moves via the party line. He meanwhile sees her and tries to woo her without her knowing that he's the guy on the other end of the line. ” - Janet Conway
 
20.
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
“ A London singleton has a crush on her cad of a boss. A Modern day version of Pride and Prejudice. ” - Janet Conway
 
21.
The Lake House (2006)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A lonely doctor who once occupied an unusual lakeside home begins exchanging love letters with its former resident, a frustrated architect. They must try to unravel the mystery behind their extraordinary romance before it's too late. (99 mins.)
 
22.
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. (120 mins.)
Director: Billy Wilder
 
23.
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
 
24.
The Truth About Cats & Dogs (1996)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
A successful veternarian & radio show host with low self-esteem asks her model friend to impersonate her when a handsome man wants to see her. (97 mins.)
Director: Michael Lehmann
“ An intelligent radio veterinarian and a sexy model play a modern day Cyrano de Bergerac in a tale to decide what attracts men more: Sexy or Smart. ” - Janet Conway
 
25.
Ever After: A Cinderella Story (1998)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
The "real" story of Cinderella. A refreshing new take on the classic fairy tale. (121 mins.)
Director: Andy Tennant
“ A French girl loses her beloved father and is raised by her wicked, new stepmother. He tries to save a servant at the castle and meets a lost and souless Prince Henry. While he is unaware of her status, he falls in love. ” - Janet Conway
 
26.
Sixteen Candles (1984)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A girl's "sweet" sixteenth birthday becomes anything but special as she suffers from every embarrassment possible. (93 mins.)
Director: John Hughes
“ Everyone forgets Andie's sweet sixteen, while her family prepares for her sister's wedding. Meanwhile, Andie has angst for the most popular boy in school. ” - Janet Conway
 
27.
Chocolat (2000)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A woman and her daughter open a chocolate shop in a small French village that shakes up the rigid morality of the community. (121 mins.)
 
28.
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
“ A couple find they have some unfinished business after 10 years of divorce. ” - Janet Conway
 
29.
Much Ado About Nothing (1993)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Young lovers Hero and Claudio, soon to wed, conspire to get verbal sparring partners and confirmed singles Benedick and Beatrice to wed as well. (111 mins.)
Director: Kenneth Branagh
 
30.
Fever Pitch (2005)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
Lindsay is stuck in the middle of her relationship with Ben and his passion for the Boston Red Sox. (104 mins.)
“ An obsessed Red Sox fan falls for a busy professional. She has no idea how obsessed he is until the season starts. ” - Janet Conway
 
31.
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
“ Charming man tries to get to the bottom of why thugs are trying to persue a woman on the run. She falls in love with him, while he keeps lying about who he is. ” - Janet Conway
 
32.
Under the Tuscan Sun (2003)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A writer impulsively buys a villa in Tuscany in order to change her life. (113 mins.)
Director: Audrey Wells
 
33.
Gentlemen Prefer Blondes (1953)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Showgirls Lorelei Lee and Dorothy Shaw travel to Paris, pursued by a private detective hired by the suspicious father of Lorelei's fiancé, as well as a rich, enamored old man and many other doting admirers. (91 mins.)
Director: Howard Hawks
“ Two beautiful women meet men on a cruise to France. One wants a steamy romance, one wants a rich man. ” - Janet Conway
 
34.
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
“ Two best friends agree to marry, if neither is married by 28. He calls on her 28th birthday to inform her that he's engaged to someone else. ” - Janet Conway
 
35.
Definitely, Maybe (2008)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A political consultant tries to explain his impending divorce and past relationships to his 11-year-old daughter. (112 mins.)
Director: Adam Brooks
“ A little girl wants to know how her divorcing parents met. Her father recounts the three loves of his life, while she tries to figure out which one is her mother. ” - Janet Conway
 
36.
Something's Gotta Give (2003)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A swinger on the cusp of being a senior citizen with a taste for young women falls in love with an accomplished woman closer to his age. (128 mins.)
Director: Nancy Meyers
 
37.
Working Girl (1988)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
When a secretary's idea is stolen by her boss, she seizes an opportunity to steal it back by pretending she has her boss' job. (113 mins.)
Director: Mike Nichols
“ A secretary plays by all the rules to earn a big job on Wall Street, only to find that the rules a played a different way. After her big idea is stolen by her boss and mentor, she poses temporarily with her job and finds bigger success...until she is discovered. ” - Janet Conway
 
38.
Romancing the Stone (1984)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A romance writer sets off to Colombia to ransom her kidnapped sister, and soon finds herself in the middle of a dangerous adventure. (106 mins.)
Director: Robert Zemeckis
“ A lonely New York romance book author finds out that her sister has been kidnapped in Columbia. He goes to Columbia to give them whatever the kidnappers want, but gets derailed on the way. A expatriot exotic bird collector rescues her and helps her to return to the city, while being chased by corrupt law men and drug dealers. ” - Janet Conway
 
39.
The Last of the Mohicans (1992)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Three trappers protect a British Colonel's daughters in the midst of the French and Indian War. (112 mins.)
Director: Michael Mann
 
40.
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