Entertainment The Best R-Rated Romantic Comedies  

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7.5k votes 1k voters 147.5k views 114 items

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List of R-Rated romantic comedies, ranked from best to worst with movie trailers when available. This list takes the best R-Rated romantic comedies and pits them against each other to see once and for all what the greatest R-Rated romantic comedy movie of all time is.

You can also see the best comedies that are currently streaming on both Amazon Prime and Netflix Instant

This list of popular R-Rated romantic comedies includes information like who directed the film, when it was released, and which actors starred in the movie. If you think the top R-Rated romantic comedy movie isn't as high as it should be, then be sure to vote it up so it can take its rightful place among the other great R-Rated romantic comedy films on this list.

If you're trying to find a specific R-Rated romantic comedy film you can search this list and filter to find what you're looking for.List contains movies like The 40-Year-Old Virgin and When Harry Met Sally... If you're trying to find out "What are the best R-Rated romantic comedies?" and "What are the most famous R-Rated romantic comedies?" then this list is the perfect resource for you. Use this list if you're looking for some new romantic comedies that are rated R. Between Netflix, Amazon Prime, and other services, there are thousands of great romantic comedies rated R, so get out there and start watching. Share this list after re-ranking it to fit the order you think it should be in. (114 items)

What kind of directors have worked on Romantic comedy R movies in the past? Woody Allen and Steven Soderbergh both have, as have other great directors.

list ordered by
1
189 74
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Mila Kunis, Kristen Bell, Russell Brand
Forgetting Sarah Marshall is a 2008 American romantic comedy-drama film directed by Nicholas Stoller and starring Jason Segel, Kristen Bell, Mila Kunis and Russell Brand. The film, which was ...more
2
238 104
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Julia Roberts, Richard Gere, Hank Azaria
Pretty Woman is a 1990 American romantic comedy film set in Los Angeles. Written by J. F. Lawton and directed by Garry Marshall, it stars Richard Gere and Julia Roberts, and features Hector ...more
3
196 88
Wedding Crashers is listed (or ranked) 3 on the list The Best R-Rated Romantic Comedies
Rachel McAdams, Bradley Cooper, Isla Fisher
Wedding Crashers is a 2005 American romantic comedy film directed by David Dobkin. It stars Owen Wilson, Vince Vaughn, and Christopher Walken. Will Ferrell also has a notable cameo appearance. ...more
4
170 72
When Harry Met Sally... is listed (or ranked) 4 on the list The Best R-Rated Romantic Comedies
Meg Ryan, Billy Crystal, Carrie Fisher
When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and directed by Rob Reiner. It stars Billy Crystal as Harry and Meg Ryan as Sally. The story follows the ...more
5
186 82
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ChadArndt added Alyson Hannigan, Tara Reid, Shannon Elizabeth
American Pie is a 1999 teen comedy film written by Adam Herz and directed by brothers Paul and Chris Weitz, in their directorial film debut. It is the first film in the American Pie theatrical ...more
6
189 85
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Keira Knightley, Elisha Cuthbert, Liam Neeson
Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by Richard Curtis. The screenplay delves into different aspects of love as shown through ten separate ...more
7
179 86
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Elizabeth Banks, Kat Dennings, Steve Carell
The 40-Year-Old Virgin is a 2005 American romantic comedy film written, produced and directed by Judd Apatow, about a middle-aged man's journey to finally lose their virginity. It was co-written ...more
8
141 62
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Cameron Diaz, Sarah Silverman, Ben Stiller
There's Something About Mary is a 1998 comedy film, directed by the Farrelly brothers, Bobby and Peter. It stars Cameron Diaz, Matt Dillon and Ben Stiller, and it is a combination of romantic ...more
9
157 79
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Natalie Portman, Ashton Kutcher, Kevin Kline
A guy and girl try to keep their relationship strictly physical, but it's not long before they learn that they want something more.
10
130 65
What Men Want is listed (or ranked) 10 on the list The Best R-Rated Romantic Comedies
Taraji P. Henson, Wendi McLendon-Covey, Max Greenfield
What Men Want is a 2019 romantic fantasy-comedy film directed by Adam Shankman. A woman (Taraji P. Henson) is boxed out by the male sports agents in her profession, but gains an unexpected edge ...more
11
128 65
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Renée Zellweger, Hugh Grant, Colin Firth
Bridget Jones's Diary is a 2001 British romantic comedy film directed by Sharon Maguire. It is based on Helen Fielding's novel of the same name which is a reinterpretation of Austen's Pride and ...more
12
127 67
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Katherine Heigl, Gerard Butler, Craig Ferguson
The Ugly Truth is a 2009 American romantic comedy film starring Katherine Heigl and Gerard Butler. The film was released in North America on July 24, 2009 by Columbia Pictures.
13
112 58
Jerry Maguire is listed (or ranked) 13 on the list The Best R-Rated Romantic Comedies
Tom Cruise, Lucy Liu, Renée Zellweger
Jerry Maguire is a 1996 American romantic comedy-drama sports film written, produced and directed by Cameron Crowe, and stars Tom Cruise, Cuba Gooding Jr. and Renée Zellweger. It was ...more
14
100 50
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Scarlett Johansson, Bill Murray, Anna Faris
Lost in Translation is a 2003 American comedy-drama film written and directed by Sofia Coppola. It stars Bill Murray, Scarlett Johansson, Giovanni Ribisi, Anna Faris, and Fumihiro Hayashi. The ...more
15
92 47
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Hugh Grant, Andie MacDowell, Rowan Atkinson
This film is a 1994 British romantic comedy film directed by Mike Newell. It was the first of several films by screenwriter Richard Curtis to feature Hugh Grant. It was made in six weeks and ...more
16
101 58
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Jackie Evancho, Alice Eve, Krysten Ritter
She's Out of My League is a 2010 American romantic comedy film directed by Jim Field Smith and written by Sean Anders and John Morris. The film stars Jay Baruchel and Alice Eve, and was produced ...more
17
63 33
Grosse Pointe Blank is listed (or ranked) 17 on the list The Best R-Rated Romantic Comedies
Dan Aykroyd, John Cusack, Hank Azaria
Grosse Pointe Blank is a 1997 American comedy film directed by George Armitage, and starring John Cusack, Minnie Driver, Alan Arkin and Dan Aykroyd. The film received positive reviews from ...more
18
24 3
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C. Mitchell George added Emma Stone, Mila Kunis, Justin Timberlake
Friends with Benefits is a 2011 American romantic comedy film directed by Will Gluck and starring Justin Timberlake and Mila Kunis. The film features a supporting cast that includes Patricia ...more
19
58 32
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ChadArndt added Kevin Costner, Susan Sarandon, Tim Robbins
Bull Durham is a 1988 American romantic comedy sports film. It is partly based upon the minor league experiences of writer/director Ron Shelton and depicts the players and fans of the Durham ...more
20
63 40
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Kevin Costner, Rene Russo, Don Johnson
Tin Cup is a 1996 romantic comedy film co-written and directed by Ron Shelton, and starring Kevin Costner and Rene Russo with Cheech Marin and Don Johnson in major supporting roles.
21
65 53
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Elizabeth Banks, Seth Rogen, Traci Lords
This film is a 2008 romantic comedy film written and directed by Kevin Smith, distributed by The Weinstein Company, and starring Seth Rogen and Elizabeth Banks. It is Smith's second film not to ...more
22
61 54
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Sandra Oh, Virginia Madsen, Thomas Haden Church
Sideways is a 2004 American comedy-drama film written by Jim Taylor and Alexander Payne and directed by Payne. A film adaptation from Rex Pickett's novel of the same name, Sideways follows two ...more
23
49 41
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Julia Roberts, Matt Damon, Vincent D'Onofrio
Mystic Pizza is a 1988 American coming-of-age film directed by Donald Petrie. It stars Annabeth Gish, Julia Roberts, and Lili Taylor. The film also stars Vincent D'Onofrio, William R. Moses, ...more
24
43 35
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Meryl Streep, Oprah Winfrey, Alec Baldwin
It's Complicated is a 2009 American romantic comedy film written and directed by Nancy Meyers. It stars Meryl Streep as a successful bakery owner and single mother of three who starts a secret ...more
25
43 36
The Good Girl is listed (or ranked) 25 on the list The Best R-Rated Romantic Comedies
Jennifer Aniston, Zooey Deschanel, Jake Gyllenhaal
The Good Girl is a 2002 comedy-drama film directed by Miguel Arteta from a script by Mike White, and stars Jennifer Aniston, Jake Gyllenhaal and John C. Reilly.