#61 The Bachelor and the Bobby-Soxer
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
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
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)
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
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
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
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
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.
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
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.