Best Romantic Comedy Classics

The best romantic comedy movies are the ones that take a break from the expected storyline and truly deliver a powerful romance with an even more powerful sense of humor. They contain well-rounded characters designed in such a manner that the average man or woman can relate with them, even when those characters are placed in less-than-average situations.

Best Romantic Comedy Classics
Romantic comedies come in three separate styles. There are comedic films that add a little romance, romantic films that add a little comedy and films that weave together both concepts in even portions. The best romantic comedy films take the third approach, weaving both romance and comedy into a perfectly balanced story with some sort of uplifting ending. This creates a powerful romantic comedy that can stand the test of time and become a true classic.

Annie Hall (1977)
The 1977 romantic comedy Annie Hall, is considered a requisite film for any Woody Allen or Diane Keaton fan. The film details the rise and fall of the relationship between two self-involved people living in New York City.

The story in Annie Hall revolves around the neurotic Alvey, played by Allen, and the kooky Annie, played by Keaton. As their relationship slowly falls apart, Allen uses the typical sarcasm and neurotic imagery for which he is legend. From pulling out the director of a movie to tell the loud guy in line he doesn't know anything about the film to subtitles reveling a characters true thoughts, it's all classic Woody Allen humor. 

Harold and Maude (1971)
Harold and Maude is a disturbing, hilarious, sarcastic, moving and thoughtful romantic comedy from 1971. It contains no actual sexual scenes, which audiences tend to prefer, since the story is about a rich 20-year-old boy who falls in love with a poor 79-year-old woman.

The rich boy in Harold and Maude, played by Bud Cort, enjoys faking suicide to torture his mother and scare off dates. The old woman, played by Ruth Gordon, is an anarchist who lives in pure freedom, stealing cars when she needs to drive and greeting each morning with open arms. Through their relationship the old woman teaches the boy how to truly love life and himself. Though the ending is sad, it is also uplifting.

The Philadelphia Story (1940)
The Philadelphia Story was released in 1940 and stars legends Katharine Hepburn, Cary Grant and James Stewart. Known as a comedy of manners, the intensely witty script made the movie a timeless gem.

The Philadelphia Story begins as socialite Tracy, played by Hepburn, is about to get married. Her ex-husband (Grant) and his assistant (Stewart) show up a few days before the wedding, determined to get the inside scoop for a gossip magazine. However, both Grant and Stewart fall for Hepburn and she is forced to choose one of three suitors.

When Harry Met Sally (1989)
When Harry Met Sally, released in 1989, is often listed as one of the best romantic comedies ever created. When Harry (Billy Crystal) first meets Sally (Meg Ryan), things do not go well. Harry believes men and women cannot be friends without sex becoming a problem and Sally disagrees. The question becomes the central point of the story.

The two characters in When Harry Met Sally keep crossing paths in the following years, eventually becoming friends. When the friendship becomes sexual, both characters have hard questions to face. The entire movie weaves together witty views of the tale from male and female perspectives.