Holidays & Seasonal

Valentine's Day Themed Movies

Wishing everyone a Happy Valentine’s Day, and presenting a few Valentine’s themed movie clips that may inspire you to watch with these films with the lights off (or on in a few cases, lol).

valentines day, happy valentines day, valentines heart, tree of hearts, field of red flowers


Best Valentine’s Day Theme Movies

  1. Some Like It Hot (1959) has Tony Curtis and Jack Lemmon disguising themselves in drag, to go on the lam after seeing the Saint Valentine’s Day Massacre first-hand. This Billy Wider comedy is a favorite at any time of the year, but well worth a watch with your honey if you both like classic film comedies.

Marilyn Monroe, Tony Curtis, Jack Lemmon, and George Raft (a perennial gangster in films) are featured in the Some Like It Hot movie trailer, below.

2. Valentine’s Day (2010), in which a star-studded cast of characters deal with their personal and professional couplings and uncouplings:

  • Hector Elizondo and Shirley MacLaine 
  • Jessica Alba and Ashton Kutcher
  • Julia Roberts and Bradley Cooper
  • Jennifer Garner and Patrick Dempsey
  • Eric Dane, Jessica Biel, Queen Latifah, and Jamie Foxx
  • Anne Hathaway and Topher Grace

Critics didn’t love it but Valentine’s Day did well at the box office, helped by great cast performances and a popular soundtrack that included tracks by Stevie Wonder (For Once in My Life), Ben E. King (Amor), Willie Nelson (On The Street Where You Live), Maroon 5 (The Way You Look Tonight), Glenn Miller (In The Mood), Percy Sledge (When a Man Loves a Woman), Foreigner (Feels Like the First Time), as well as Nat King Cole, Jewel, Amy Winehouse, Taylor Swift, and others.

Below, veterans Shirley MacLaine and Hector Elizondo are featured in a clip from Valentine’s Day

3. Blue Valentine (2010), starring Michelle Williams & Ryan Gosling as a married couple – before, during, and at the end of their marriage. The trailer below for Blue Valentine features stars Ryan Gosling and Michelle Williams.

4. My Bloody Valentine 3D (2009) was a remake of another, 1981 Canadian slasher flick. Unlike the earlier movie, My Bloody Valentine 3D did well at the box office, possibly due to the stars Jensen Ackles, Kerr Smith, Jamie King, Betsy Rue, and Kevin Tighe (remember him from Emergency!?).

The Lionsgate trailer for My Bloody Valentine 3D gives you a pretty good idea of what to expect, courtesy of Jamie King, Jensen Ackles, and others. 

5. In The St. Valentine’s Day Massacre (1967) film, you may not be surprised to learn there is no romance. Plenty of mob crime and violence is on the menu in this gangster flick which sticks fairly closely to the real-life murder of 7 North Side Gang members (Bugs Moran’s crew) by Al Capone‘s henchmen, in 1929 Chicago. The film starred Jason Robard as Al Capone, with George Segal, Ralph Meeker, Clint Ritchie, Joseph Campanella, David Canary, and Bruce Dern in the cast.

Below, Director Roger Corman provides the introduction and gives background on his experience filming The St. Valentine’s Day Massacre in the film trailer, which features Jason Robards.

Sending all our love to you this February 14th!

If you wonder why we celebrate Valentine’s Day at all, you  may like this article – When Valentine’s Day Traditions Began

If you’re in the mood for romance (at any time of the year), here’s my list of Best Romance Films With Older Actors

If you’re contemplating being on your own this Valentine’s day, this article may help: Surviving Valentine’s Day: Tips For 50+ Singles.

And if you like the idea of sharing a vintage Valentine’s Day greeting cards check out

Vintage Inspired Valentines 

Vintage Silent Film Stars Valentine’s Day Cards

Vintage 1930s-1940s Film Star Valentines

1950s-1960s Vintage Celebrity Valentines

Have a Happy Valentine’s Day

Anita Hamilton

50+ World editor & baby boomer writer Anita Hamilton has always been interested in the "real people" stories behind the characters that create and inhabit the world of music, books, movies, television shows, current events, history, etc. A lifelong love of research (ok, nosiness) and writing, combined with a loving and supportive family complete with 3 mini-dachshund minions, keeps her busy.

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