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Reader's Digest 50 Best Romantic Comedies of All Time

Here are Reader's Digest best romantic comedies by Kelly Bryant updated Mar 10,2023. Things taken into account are the movies staying power, box office numbers and award-show buzz when released. Enjoy.
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avg. score: 23 of 50 (47%)
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1
The Princess Bride (1987)
The Princess Bride (1987)
Rotten Tomatoes®   97%
2
Clueless (1995)
Clueless (1995)
Rotten Tomatoes®   81%
3
When Harry Met Sally... (1989)
When Harry Met Sally... (1989)
Rotten Tomatoes®   91%
4
10 Things I Hate About You (1999)
10 Things I Hate About You (1999)
Rotten Tomatoes®   70%
5
Love Actually (2003)
Love Actually (2003)
Rotten Tomatoes®   64%
6
Breakfast at Tiffany's (1961)
Breakfast at Tiffany's (1961)
Rotten Tomatoes®   89%
7
Pretty Woman (1990)
Pretty Woman (1990)
Rotten Tomatoes®   66%
8
Enchanted (2007)
Enchanted (2007)
Rotten Tomatoes®   93%
9
Mamma Mia! (2008)
Mamma Mia! (2008)
Rotten Tomatoes®   55%
10
Bridget Jones's Diary (2001)
Bridget Jones's Diary (2001)
Rotten Tomatoes®   80%
11
Tootsie (1982)
Tootsie (1982)
Rotten Tomatoes®   90%
12
13 Going on 30 (2004)
13 Going on 30 (2004)
Rotten Tomatoes®   65%
13
50 First Dates (2004)
50 First Dates (2004)
Rotten Tomatoes®   45%
14
Sleepless in Seattle (1993)
Sleepless in Seattle (1993)
Rotten Tomatoes®   75%
15
Meet the Parents (2000)
Meet the Parents (2000)
Rotten Tomatoes®   84%
16
Four Weddings and a Funeral (1994)
Four Weddings and a Funeral (1994)
Rotten Tomatoes®   96%
17
Notting Hill (1999)
Notting Hill (1999)
Rotten Tomatoes®   83%
18
The Holiday (2006)
The Holiday (2006)
Rotten Tomatoes®   50%
19
You've Got Mail (1998)
You've Got Mail (1998)
Rotten Tomatoes®   69%
20
Moonstruck (1987)
Moonstruck (1987)
Rotten Tomatoes®   94%
21
The Proposal (2009)
The Proposal (2009)
Rotten Tomatoes®   45%
22
The Wedding Singer (1998)
The Wedding Singer (1998)
Rotten Tomatoes®   69%
23
My Big Fat Greek Wedding (2002)
My Big Fat Greek Wedding (2002)
Rotten Tomatoes®   76%
24
Crazy, Stupid, Love. (2011)
Crazy, Stupid, Love. (2011)
Rotten Tomatoes®   79%
25
How to Lose a Guy in 10 Days (2003)
How to Lose a Guy in 10 Days (2003)
Rotten Tomatoes®   42%
26
Never Been Kissed (1999)
Never Been Kissed (1999)
Rotten Tomatoes®   55%
27
My Best Friend's Wedding (1997)
My Best Friend's Wedding (1997)
Rotten Tomatoes®   73%
28
27 Dresses (2008)
27 Dresses (2008)
Rotten Tomatoes®   41%
29
While You Were Sleeping (1995)
While You Were Sleeping (1995)
Rotten Tomatoes®   81%
30
Splash (1984)
Splash (1984)
Rotten Tomatoes®   92%
31
Crazy Rich Asians (2018)
Crazy Rich Asians (2018)
Rotten Tomatoes®   90%
32
The Big Sick (2017)
The Big Sick (2017)
Rotten Tomatoes®   98%
33
To All the Boys I've Loved Before (2018)
To All the Boys I've Loved Before (2018)
Rotten Tomatoes®   96%
34
Runaway Bride (1999)
Runaway Bride (1999)
Rotten Tomatoes®   46%
35
The Wedding Planner (2001)
The Wedding Planner (2001)
Rotten Tomatoes®   17%
36
Overboard (1987)
Overboard (1987)
Rotten Tomatoes®   44%
37
Serendipity (2001)
Serendipity (2001)
Rotten Tomatoes®   59%
38
Can't Buy Me Love (1987)
Can't Buy Me Love (1987)
Rotten Tomatoes®   50%
39
Can't Hardly Wait (1998)
Can't Hardly Wait (1998)
Rotten Tomatoes®   40%
40
Nick and Norah's Infinite Playlist (2008)
Nick and Norah's Infinite Playlist (2008)
Rotten Tomatoes®   75%
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