For those with an aversion to anything too sappy, the romantic comedy is the perfect bridge between romance and humor. Romantic comedies often allow people to enjoy love stories that are a little more down to earth and realistic, or at least somewhat more self aware about the ridiculous nature of cinematic romantic gestures. These romantic comedies for beginners are all films that helped establish the conventions of the rom-com as a genre. From classics like When Harry Met Sally to more modern films like The 40-Year-Old Virgin, all the below movies had a major impact when they were released.
While romance films tend to idealize romantic relationships, romantic comedies tend to show us average people navigating average relationships. Characters go through normal ups and downs where nothing is perfect, things are often funny, and people fall in love the same way we all do. These essential rom-coms often feature highly imperfect romantic leads who are just as awkward about romance as the average viewer. This is part of the reason romantic comedies tend to be so popular - people love seeing relatable characters. While most of us will never have the brooding intrigue of Casablanca's Rick Blaine, we may be as klutzy as Bridget Jones or as cynical and surly as Phil Connors of Groundhog Day.
It's highly unlikely you are completely new to the genre, but this list will serve as an intro to romantic comedies just in case you're not well versed. These must-see romantic comedies often made their stars famous and gave us scenes and jokes widely recognized today. These are truly movies everyone should watch, if only to understand the many references to films like Pretty Women and Sleepless in Seattle that dot popular culture.
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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 title characters from the time they meet just before sharing a cross-country drive, through twelve years or so of chance encounters in New York City. The film raises the question "Can men and women ever just be friends?" and advances many ideas about relationships that became household concepts, such as those of the "high-maintenance" girlfriend and the "transitional person". The origins of the film came from Reiner's return to single life after a divorce. An interview Ephron conducted with Reiner ...more on Wikipedia
Actors: Meg Ryan, Billy Crystal, Carrie Fisher, Harley Jane Kozak, Bruno Kirby, + more
Initial Release: 1989
Directed by: Rob Reiner
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 Elizondo, Ralph Bellamy, Laura San Giacomo and Jason Alexander in supporting roles. Its story centers on the down-on-her-luck Hollywood prostitute Vivian Ward who is hired by Edward Lewis, a wealthy businessman, to be his escort for several business and social functions, and their developing relationship over the course of her week-long stay with him. Originally intended to be a dark cautionary tale about class and prostitution in Los Angeles, the film was reconceived as romantic comedy with a large ...more on Wikipedia
Actors: Julia Roberts, Richard Gere, Hank Azaria, Jason Alexander, Amy Yasbeck, + more
Initial Release: 1990
Directed by: Garry Marshall
#71 on The Funniest '90s Movies
#89 on The Most Rewatchable Movies
Notting Hill is a 1999 British romantic comedy film set in Notting Hill, London, released on 21 May 1999. The screenplay was by Richard Curtis and the film was produced by Duncan Kenworthy and directed by Roger Michell. The film stars Hugh Grant, Julia Roberts, Rhys Ifans, Emma Chambers, Tim McInnerny, Gina McKee, and Hugh Bonneville. Notting Hill was well received by critics and became the highest grossing British film released that year. ...more on Wikipedia
Actors: Julia Roberts, Alec Baldwin, Mischa Barton, Hugh Grant, Emily Mortimer, + more
Initial Release: 1999
Directed by: Roger Michell
#22 on The Best Movies of 1999
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 Prejudice. The adaptation stars Renée Zellweger as Bridget, Hugh Grant as the caddish Daniel Cleaver and Colin Firth as Bridget's "true love", Mark Darcy. Production began in May 2000 and ended in August 2000, and took place largely on location in London and the Home Counties. Bridget Jones's Diary premiered on 4 April 2001 in the UK and was released to theaters on 13 April 2001 simultaneously in the UK and in the US. The film received positive reviews and was a commercial success. Zellweger was ...more on Wikipedia
Actors: Renée Zellweger, Hugh Grant, Colin Firth, Honor Blackman, Jim Broadbent, + more
Initial Release: 2001
Directed by: Sharon Maguire
#90 on The Best Rainy Day Movies
#11 on The Best Movies for Women