The 100 Best Romantic Comedies of All Time (Part Two)

#61 The Bachelor and the Bobby-Soxer

Year: 1947

Director: Irving Reis

Starring: Cary Grant, Shirley Temple and Myrna Loy

My Take: A screwball romantic comedy about the teenager Susan, who falls in love with the playboy Richard, only for him to fall in love with her sister Margaret who is a Judge (who orders him to pretend to date Susan until she gets over her crush instead of going to prison). If you haven’t seen this film, it is hilarious.

#62 Some Kind of Wonderful

Year: 1987

Director: Howard Deutch (written by John Hughes)

Starring: Eric Stoltz, Lea Thompson and Mary Stuart Masterson

My Take: For all the romantics out there who believe the best kind of love stems from friendship…

#63 Swing Time

Year: 1936

Director: George Stevens

Starring: Ginger Rogers and Fred Astaire

My Take: A Fred and Ginger romantic comedy classic! This film includes some of the best dance sequences of all time.

#64 My Man Godfrey (1936)

Year: 1936

Director: Gregory La Cava

Starring: William Powell and Carole Lombard

My Take: This romantic comedy about a socialite who hires a homeless man (with a mysterious past) to be her family’s butler (who she then falls in love with) is a must see.

#65 My Best Friend’s Wedding

Year: 1997

Director: P.J. Hogan

Starring: Julia Roberts, Dermot Mulroney, Cameron Diaz and Rupert Everett

My Take: While I personally didn’t love the ending, the film as a whole is quite memorable and a wonderful romantic comedy to watch again and again.

#66 How To Marry A Millionaire

Year: 1953

Director: Jean Negulesco

Starring: Marilyn Monroe, Lauren Bacall, Betty Grable

My Take: Three struggling women try to find millionaires to marry, but end up finding real love instead. If you love these three actresses, then this film is a must see.

#67 Pretty in Pink

Year: 1986

Director: Howard Deutch (John Hughes the writer)

Starring: Molly Ringwald, Andrew McCarthy and Jon Cryer

My Take: This star-crossed teen love story about Andie and Blane, two teenagers from opposites sides of the track, is a John Hughes classic with heart and humor.

#68 The Pirate

Year: 1948

Director: Vincente Minnelli

Starring: Judy Garland and Gene Kelly

My Take: This musical, romantic comedy starring Judy Garland and Gene Kelly about a girl who falls in love with the idea of the infamous pirate Macoco is great fun.  The story gets even more fun (and ridiculous) when a singer falls in love with the girl and pretends to be said legendary pirate. This is a lesser known gem worth watching.

#69 Austenland

Year: 2013

Director: Jerusha Hess

Starring: Keri Russell and JJ Feild

My Take: If you take this film too seriously, then you probably won’t enjoy it. However, if you go into this satirical romantic comedy and fully embrace the silliness, you may love it as much as I did. Plus, how perfect was the casting of Keri Russell as Jane who just so happens to be obsessed with an unattainable crush (aka Mr. Darcy)?

#70 Woman of the Year

Year: 1942

Director: George Stevens

Starring: Spencer Tracy and Katharine Hepburn

My Take: This film is Tracy and Hepburn magic. Two reporters, Sam and Tess, fall in love and get married only to have a strained relationship because of how busy Tess is.

By on May 20th, 2015

About Amber Topping

Amber works as a writer and digital publisher full-time and fell in love with stories and imagination at an early age. She has a Humanities and Film Degree from BYU, co-created The Silver Petticoat Review, contributed as a writer to various magazines, and has an MS in Publishing from Pace University, where she received the Publishing Award of Excellence and wrote her thesis on transmedia, Jane Austen, and the romance genre. Her ultimate dreams are publishing books, writing and producing movies, traveling around the world, and forming a creative village of talented storytellers trying to change the world through art.

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1 thought on “The 100 Best Romantic Comedies of All Time (Part Two)”

  1. Lots of favorites here. 13 Going on 30 is charming; love Sweet Home Alabama; Warm Bodies is oddly eccentric, but in a very sweet way; Austenland, just yes; Miss Pettigrew, Legally Blonde and The Proposal (Sandra Bullock is great) are always fab choices. Oh, and I heart Knight and Day. Such a cute flick. It’s been eons since I watched Sabrina or the “Bachelor” Shirley Temple film. Perhaps it’s time to remedy that. 🙂


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