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The 25 Best Romantic Comedies of All Time According to Vanity Fair

Their ultimate list is an eclectic mix, containing everything from black-and-white classics to, well, How to Lose a Guy in 10 Days. And while every single pick may not contain every element commonly associated with the romantic comedy, they all fit the American Film Institute's broad definition of "a genre in which the development of a romance leads to comic situations." Of course, they're all funny, too.
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1
When Harry Met Sally... (1989)
When Harry Met Sally... (1989)
Rotten Tomatoes®   91%
2
You've Got Mail (1998)
You've Got Mail (1998)
Rotten Tomatoes®   69%
3
Clueless (1995)
Clueless (1995)
Rotten Tomatoes®   81%
4
Bridget Jones's Diary (2001)
Bridget Jones's Diary (2001)
Rotten Tomatoes®   80%
5
10 Things I Hate About You (1999)
10 Things I Hate About You (1999)
Rotten Tomatoes®   70%
6
Groundhog Day (1993)
Groundhog Day (1993)
Rotten Tomatoes®   97%
7
Notting Hill (1999)
Notting Hill (1999)
Rotten Tomatoes®   83%
8
It Happened One Night (1934)
It Happened One Night (1934)
Rotten Tomatoes®   99%
9
Broadcast News (1987)
Broadcast News (1987)
Rotten Tomatoes®   98%
10
Sleepless in Seattle (1993)
Sleepless in Seattle (1993)
Rotten Tomatoes®   75%
11
My Best Friend's Wedding (1997)
My Best Friend's Wedding (1997)
Rotten Tomatoes®   73%
12
His Girl Friday (1940)
His Girl Friday (1940)
Rotten Tomatoes®   99%
13
Down With Love (2003)
Down With Love (2003)
Rotten Tomatoes®   60%
14
The 40 Year Old Virgin (2005)
The 40 Year Old Virgin (2005)
Rotten Tomatoes®   85%
15
Moonstruck (1987)
Moonstruck (1987)
Rotten Tomatoes®   94%
16
Four Weddings and a Funeral (1994)
Four Weddings and a Funeral (1994)
Rotten Tomatoes®   96%
17
The Apartment (1960)
The Apartment (1960)
Rotten Tomatoes®   93%
18
Amélie (2001)
Amélie (2001)
Rotten Tomatoes®   89%
19
Much Ado About Nothing (1993)
Much Ado About Nothing (1993)
Rotten Tomatoes®   90%
20
Annie Hall (1977)
Annie Hall (1977)
Rotten Tomatoes®   96%
21
Some Kind of Wonderful (1987)
Some Kind of Wonderful (1987)
Rotten Tomatoes®   75%
22
How to Lose a Guy in 10 Days (2003)
How to Lose a Guy in 10 Days (2003)
Rotten Tomatoes®   42%
23
Kissing Jessica Stein (2001)
Kissing Jessica Stein (2001)
Rotten Tomatoes®   84%
24
Something's Gotta Give (2003)
Something's Gotta Give (2003)
Rotten Tomatoes®   72%
25
My Big Fat Greek Wedding (2002)
My Big Fat Greek Wedding (2002)
Rotten Tomatoes®   76%
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