20 BEST Romantic Comedies In The Last 20 Years

These are THE BEST rom-coms from the past 20 years. In no particular order. FIRST doesn't necessarily mean BEST.

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1.
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
 
2.
10 Things I Hate About You (1999)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A pretty, popular teenager can't go out on a date until her ill-tempered older sister does. (97 mins.)
Director: Gil Junger
 
3.
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
 
4.
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
 
5.
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
 
6.
Heartbreakers (2001)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
A mother and daughter con team seduce and scam wealthy men. (123 mins.)
Director: David Mirkin
 
7.
Reality Bites (1994)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
A documentary filmmaker and her fellow Gen X graduates face life after college, looking for work and love in Houston. (99 mins.)
Director: Ben Stiller
 
8.
Serendipity (2001)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
A couple reunite 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
 
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
 
10.
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
 
11.
Excess Baggage (1997)
    1 2 3 4 5 6 7 8 9 10 5.2/10 X  
Emily has always been the rich brat who tries to pull every imaginable stunt to get attention. But one day... (101 mins.)
Director: Marco Brambilla
 
12.
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
 
13.
Watching the Detectives (2007)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
A film noir buff has his life turned on end by a femme fatale with a big adventure in mind. (91 mins.)
Director: Paul Soter
“ Cillian Murphy, Lucy Liu ” - heath_kaos
 
14.
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
 
15.
Overnight Delivery (1998)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
A man suspects his girlfriend of being unfaithful. So he sends her a letter, but than finds out that he was wrong... (87 mins.)
Director: Jason Bloom
“ Paul Rudd, Reese Witherspoon ” - heath_kaos
 
16.
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
 
17.
HouseSitter (1992)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
Con artist Gwen moves into Newton's empty house without his knowledge, and begins setting up house posing as his new wife. (102 mins.)
Director: Frank Oz
 
18.
Groundhog Day (1993)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A weatherman finds himself living the same day over and over again. (101 mins.)
Director: Harold Ramis
 
19.
Just Friends (2005)
    1 2 3 4 5 6 7 8 9 10 6.2/10 X  
While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with -- a woman whose rejection of him turned him into a ferocious womanizer. (96 mins.)
Director: Roger Kumble
 
20.
Mystery Date (1991)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
A teenage boy would like to meet with a very pretty, blonde girl who lives in the next door. His elder... (97 mins.)
Director: Jonathan Wacks