#21 Annie Hall

Year: 1977

Director: Woody Allen

Starring: Woody Allen and Diane Keaton

My Take: This Oscar winning romantic comedy is one of Woody Allen’s finest films with Diane Keaton at her neurotic best. A classic for sure with witty fast talking dialogue and memorable characters.

#22 City Lights

Year: 1931

Director: Charlie Chaplin

Starring: Charlie Chaplin and Virginia Cherrill

My Take: I loved this beautiful silent film about the Tramp who falls in love with a blind girl. It’s charming, funny and beautifully made.

#23 The Princess Bride

https://www.youtube.com/watch?v=VYgcrny2hRs

Year: 1987

Director: Rob Reiner

Starring: Cary Elwes and Robin Wright

My Take: Also a fantasy and a fairy tale, this romantic comedy is sure to always be a fan favorite. Besides the many memorable quotes, the romance is one for the story books…literally.

#24 Kate and Leopold

Year: 2001

Director: James Mangold

Starring: Meg Ryan and Hugh Jackman

My Take: Kate and Leopold is pure romantic fun! Hugh Jackman plays the epitome of the perfect man we love to fantasize about. Not only is he handsome, charming, intelligent, chivalrous and kind, but he’s also from a different time period. So it’s fun to watch our “Mr. Darcy” fantasy unfold in the modern world. In all, Leopold makes the ideal leading man in one of the most entertaining traditional romantic comedies.

#25 The Holiday

Year: 2006

Director: Nancy Meyers

Starring: Kate Winslet, Jack Black, Cameron Diaz and Jude Law

My Take: Perhaps because I relate quite a bit to the two female characters, or maybe because I absolutely adore Jude Law, this is one of my favorites. There’s something charming about this tale about two different women who go on vacation from their lives only to find love.

#26 Romancing the Stone

Year: 1984

Director: Robert Zemeckis

Starring: Michael Douglas and Kathleen Turner

My Take: This romantic comedy blends itself into a real life romance novel type adventure when a shy romance novelist goes to Colombia to rescue her kidnapped sister and finds herself stuck on an adventure with an adventurous bad boy. It’s a lot of fun with many laugh out loud moments.

#27 Much Ado About Nothing

https://www.youtube.com/watch?v=bYj-2vFLbtc

Year: 1993

Director: Kenneth Branagh

Starring: Emma Thompson, Kenneth Branagh, Kate Beckinsale and Robert Sean Leonard

My Take: The first time I watched this particular Shakespeare adaptation from Branagh, I laughed so hard I had tears rolling down my face. It’s hard to top the romantic and comedic chemistry between Emma Thompson and Kenneth Branagh as the notorious Beatrice and Benedick. They perfected Shakespeare’s (who really was ahead of his time) romantic comedy for the silver screen.

#28 His Girl Friday

Year: 1940

Director: Howard Hawks

Starring: Cary Grant and Rosalind Russell

My Take: This fast talking romantic comedy classic is certainly one of the greatest of all time with Cary Grant and Rosalind Russell at the top of their game. Hawks certainly knows how to do romantic comedy well in this story of two reporters in the midst of a divorce.

#29 Penelope

Year: 2006

Director: Mark Palansky

Starring: Christina Ricci and James McAvoy

My Take: This wonderful film (though it’s even better with the longer, full European release) doesn’t get as much love as it deserves. The story about a young woman with a pig nose who can only break her family’s curse when a blue blood loves her for who she is, perfectly blends the Beauty and the Beast fairy tale with a romantic comedy. It’s funny and delightful with James McAvoy as the perfect leading man.

#30 Singin’ in the Rain

Year: 1952

Directors: Stanley Donen and Gene Kelly

Starring: Gene Kelly and Debbie Reynolds

My Take: Both romantic comedy and classic musical, this is one of the best films of all time with an unforgettable soundtrack, iconic dance moves and a memorable romance with a lot of humor thrown into the mix.

#31 Populaire

Year: 2012

Director: Régis Roinsard

Starring: Déborah François and Romain Duris

My Take: This lesser known French period gem tells the story of Rose, a young secretary who’s horrible at her job but is also a master typist. Her handsome boss trains her to become the best and enters her into competitions. Of course, a romance develops between the two. I can’g gush about how cute this film is!

#32 The Philadelphia Story

Year: 1940

Director: George Cukor

Starring: Cary Grant, Katharine Hepburn and Jimmy Stewart

My Take: A romantic triangle done well…When Tracy’s ex-husband as well as a reporter show up before her wedding all kinds of craziness ensues! This is a must watch film including fantastic performances from some of the greatest actors of all time.

#33 Something’s Gotta Give

Year: 2003

Director: Nancy Meyers

Starring: Diane Keaton and Jack Nicholson

My Take: Nicholson and Keaton shine on screen together in a film that’s funny from start to finish. The story of an aging playboy who finally falls in love with a woman his own age is both endearing as well as hilarious.

#34 The Awful Truth

Year: 1937

Director: Leo McCarey

Starring: Irene Dunne and Cary Grant

My Take: Part screwball, this romantic comedy about a couple on the verge of divorce had me in stitches for the entire duration. The two try to sabotage each other’s attempt at new romances before their divorce becomes final and it is a lot of fun to watch.

#35 Groundhog Day

Year: 1993

Director: Harold Ramis

Starring: Andie MacDowell and Bill Murray

My Take: A wonderful film about a weatherman who keeps experiencing the same day on repeat. Thankfully, in the process he’s able to fall in love.

#36 I Know where I’m Going!

Year: 1945

Directors: Michael Powell and Emeric Pressburger

Starring: Wendy Hiller and Roger Livesey

My Take: A lesser known romantic comedy that takes place in the Scottish Highlands and is steeped in Scottish folklore. It’s a beautiful film everyone should check out.

#37 10 Things I Hate About You

Year: 1999

Director: Gil Junger

Starring: Heath Ledger, Julia Styles, Joseph Gordon-Levitt and Larisa Oleynik

My Take: This modern retelling of The Taming of the Shrew is one of the best teen romantic comedies ever. Plus, it has a young Heath Ledger singing and dancing so as to woo the “shrew” Kat, which is always great on a re-watch!

#38 Shakespeare Retold: The Taming of the Shrew

Year: 2005

Director: David Richards

Starring: Rufus Sewell and Shirley Henderson

My Take: Also a modern retelling of Taming of the Shrew, this adaptation is HILARIOUS. The chemistry between the two sizzles while the laughs never stop. It’s one funny scene after another, while also being completely romantic. If you haven’t seen it, check the film out right away.

#39 Roman Holiday

Year: 1953

Director: William Wyler

Starring: Gregory Peck and Audrey Hepburn

My Take: The story of a princess who runs away from home to experience the real world is an unforgettable one. Soon, she falls for an American newspaper man, but can they really have their happy ending? I loved this little fairy tale of a film for all it’s charm and humor.

#40 My Big Fat Greek Wedding

Year: 2002

Director: Joel Zwick

Starring: Nia Vardalos and John Corbett

My Take: This breakout hit has become one of the most popular romantic comedies ever and was even nominated for Best Original Screenplay at the Academy Awards. The script (also from star Vardalos) is clever, witty, funny and memorable.