10 Best Romantic Comedies of All Time

Romantic comedies are some of the best movies that every come out of Hollywood. There is a little bit of something for everyone in the good ones. This is a list of my top ten romantic comedies of all time. I hope you enjoy!

10. Annie Hall

Released: 1977

Directed by: Woody Allen

Written by: Woody Allen & Marshall Brickman

Starring: Woody Allen & Diane Keaton

It’s hard to have any “best of” list without having something by this legendary American filmmaker. Even though I’m not a huge fan (especially of his more recent work including Melinda & Melinda and Vickie Christina Barcelona), you still have to appreciate this classic tale of two lovers who don’t end up together.

9. While You Were Sleeping

Released: 1995

Directed by: Jon Turteltaub

Written by: Daniel G. Sullivan & Fredric LeBow

Starring: Sandra Bullock & Bill Pullman

One of my favorite holiday-time movies, this stars the lovable Sandra Bullock. The director, Jon Turteltaub is also known for his work on the National Treasure movies. It is hilarious and sweet from beginning (saving a man’s life on train tracks) to end (a fairytale proposal).

8. Some Like It Hot

Released: 1959

Directed by: Billy Wilder

Written by: Billy Wilder & I.A.L. Diamond

Starring: Marilyn Monroe & Tony Curtis

Starring the lovely Marilyn Monroe, this is a crazy tale filled with disguises, lies, and laugh out loud sequences that is sure to please any film lover!

7. Pretty Woman

Released: 1990

Directed by: Garry Marshall

Written by: J.F. Lawton

Starring: Julia Roberts & Richard Gere

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You can’t have a romantic comedy list without America’s sweetheart, Julia Roberts. This movie was an instant classic about a prostitute turned fairy tale princess that continues to melt the hearts of every woman who turns it on!

6. City Lights

Released: 1931

Directed by: Charles Chaplin

Written by: Charles Chaplin

Starring: Charles Chaplin & Virginia Cherrill

In my opinion, this is Chaplin’s best work. He pulled triple duty on this film: acting, writing, and directing. It is the tale of a homeless person who tricks a blind woman into thinking he’s a millionaire, but you can’t help but love him for it!

5. Princess Bride

Released: 1987

Directed by: Rob Reiner

Written by: William Goldman

Starring: Cary Elwes & Robin Wright Penn

One of the most often quoted pieces of film in the last quarter of a century, I just love this movie! It is a story within a story of a grandfather reading his sick grandson a book about a couple separated by destiny and brought back together by true love (with a lot of action packed and comedic scenes in between).

4. You’ve Got Mail

Released: 1998

Directed by: Nora Ephron

Written by: Nora Ephron & Delia Ephron

Starring: Tom Hanks & Meg Ryan

It was hard to decide between two different Nora Ephron movies for this list (Sleepless in Seattle, also starring Hanks and Ryan). I arrived at this one because I think it has a tad bit more comedy in it. It’s an updated, online version of the 1940s The Shop Around The Corner. Two fellow e-mailers fall in love through their words while they are both in serious relationships with other people. They eventually discover that they have competing businesses, but that doesn’t matter to them in the end.

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3. An Affair To Remember

Released: 1957

Directed by: Leo McCarey

Written by: Delmer Daves, Donald Ogden Stewart, & Leo McCarey

Starring: Carey Grant & Deborah Kerr

Carey Grant is at his best in this classic movie about a couple that meet and fall in love. They make plans to meet atop the Empire State Building six months later, but something tragic keeps them from it. This movie probably has the least amount of comedy in it, but the highest level of romance!

2. As Good As It Gets

Released: 1997

Directed by: James L. Brooks

Written by: Mark Andrus & James L. Brooks

Starring: Jack Nicholson & Helen Hunt

One of my favorite movies in any genre, this is an unlikely love story that includes two Academy Award winning performances by it’s lead actor and actress. Nicholson plays an Obsessive Compulsive writer who is obsessed with the waitress (Helen Hunt) at his most frequented restaurant. What begins as selfishness, ends up as true, sacrificial love.

1. Notting Hill

Released: 1999

Directed by: Roger Michell

Written by: Richard Curtis

Starring: Julia Roberts & Hugh Grant

This movie is top five on my all-time list of all films. Pitch perfect performances by Grant and Roberts as well as a stellar (mostly British) supporting cast make the film great. The story is of a the whirlwind romance between a famous American actress who bumps into (literally) a travel book shop owner in Notting Hill, England.