10 Sad Romantic Movies

Grab your tissue for this list of 10 sad romantic movies. Even when a romance ends happily ever-after, it can still be sad. Some of these films are tragic love stories that tug on your heart strings.

  1. "Gone With the Wind" (1939) This movie is an adaptation of the 1939 novel by Margaret Mitchell. It’s the rocky love story of Scarlett O’Hara (Vivien Leigh) and Rhett Butler (Clark Gable). Known for it’s historical reference, it is set in the south during the civil war.  The most popular quote from this movie is in the last scene when Scarlett asks Rhett what she will do without him. His answer: “Frankly, my dear, I don’t give a damn.”
  2. "West Side Story" (1961) One of the saddest romantic stories, this film is an adaptation of the Broadway musical, which was inspired by Shakespeare’s “Romeo and Juliet”. It’s a tragic love story between Tony (Richard Beymer) and Maria (Natalie Wood) set against the backdrop of rival gangs.
  3. "The Notebook" (2004) This is one of the most beautifully sad movies ever made. It’s based on the novel by Nicholas Sparks. It’s really two love stories that tie together towards the end. The first love story is that of Allie (Rachel McAdams) and Noah (Ryan Gosling), two kids on different sides of the social spectrum in the 1940s. It’s also the story of two elderly people in a nursing home who's love is threatened by age and illness.
  4. "Love Story" (1970) Young love in movies seems to be doomed. This movie's sad romantic plot is timeless. Oliver Barrett IV (Ryan O’Neal) falls in love with Jennifer Cavelleri (Ali MacGraw) while at college. They marry after graduation and Oliver’s disapproving father cuts him off, leaving the couple to struggle to pay for him going to law school. Things seem to be going good, until the couple tries to have a child and learns that their love will be ripped apart by illness.
  5. "City of Angels" (1998) This movie is a remake of the 1987 German film “Wings of Desire”. It’s about an angel, Seth (Nicolas Cage), and the human he falls for, Maggie Rice (Meg Ryan). Seth becomes human and stays with Maggie. But their love comes to a sad end and Seth learns that it is better to love for an instant than live an eternity without knowing love.
  6. "Pearl Harbor" (2001) This is a sad romance and it is also a period piece that is set against the sadness of war. This movie tells the story of a love triangle. It stars Ben Affleck, Josh Hartnett and Kate Backingsale.
  7. "Tristan and Isolde" (2006) This is a sad. romantic movie straight from legend. The ill-fated love of Tristan and Isolde has been compared to that of Romeo and Juliet. In fact that was even used in the advertising for the movie. It stared James Franco and Sophia Myles.
  8. "Elizabethtown" (2005) Things aren’t going too good for Drew Baylor (Orlando Bloom) as he has to deal with a failed project at work that cost him his job and then deal with the death of his father. He’s in a bad place when he travels to his father’s hometown and meets grieving widow, Claire (Kristan Dunst). Through their pain they both find love. The ending of this one is a perfectly written tear jerker
  9. "Sweet November" (1968) This is the love story of Charlie (Anthony Newley), a workaholic that has lost touch with the world around him, and Sara (Sandy Dennis), an out-of-the-box-thinker that is on a mission to do as much good as she can. Sara convinces Charlie to stay with her for a month, claiming she will change his out look on life. Romance takes hold but comes to a sad end when Sara reveals why they can only have the month of November to spend together. The film was remade in 2001 but it was labeled a poor imitation.
  10. "P.S. I Love You" (2007) This is the story of Holly (Hilary Swank) and Gerry (Gerard Butler) and how their love lives on even after Gerry dies. Before his death he planned a serious of messages to be delivered to Holly, all ending in “P.S. I Love You.” It’s beautiful and tragic, if not a little stalker-ish.
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