Top 20 Saddest Romantic Movies of All Time

Top 20 Saddest Romantic Movies

Welcome to MsMojo, and today we’re counting down our picks for the Top 20 Saddest Romantic Movies.

For this list, we’ll be looking at the movies that have broken millions of viewers' hearts through the tragic circumstances behind the characters' stories. Since this means we'll be discussing the heartbreaking nature of the plots in detail, here's your big Spoiler Alert!

Which romantic movie made you most feel the characters' pain? Let us know in the comments.

#20: “Wuthering Heights” (2011)

The destructive potential that comes with love is the basis for the famous story of "Wuthering Heights,” with the characters never finding peace as a result. In this period drama, a young Heathcliff is taken in as a foster child by the Earnshaw family, where he develops a romantic dynamic with the family's daughter Catherine. The story takes place across their youths and adulthood where Heathcliff and Catherine are unable to make their love official due to a combination of societal pressures and his intense jealousy toward her suitors. Yet, their feelings evolve into toxic levels, as Heathcliff essentially ruins her marriage while never managing to be with her. Love isn't always enough, and the characters' inability to see this hurts everyone involved.

#19: “Love Story” (1970)

Widely known for its melancholic soundtrack and a memorable one-liner about the importance of love, this movie is designed to be the ultimate tragic romance. Coming from different backgrounds, Oliver and Jenny's feelings remain unflinching in the face of frequent challenges, which includes financial instability and the inability to have children. Through it all, "Love Story" stresses the importance of commitment, as Oliver and Jenny's love empowers them to make the best of whatever situation they're in as long as they're together. However, the revelation of her cancer becomes a mountain too great to climb, with the couple's marriage meeting a heartbreaking conclusion. Overall, the movie delivers a painfully short romance, but ensures the couple's love remains preserved.

#18: “Atonement” (2007)

This drama shows how a simple love story turns into a lifetime of sorrow due to a misunderstanding. Set during World War II, Briony mistakes her sister Cecilia's romance with Robbie as the latter forcing himself on her. This eventually results in Briony later accusing Robbie of doing the same to a different relative, which leads to Robbie getting sent to prison and tearing him and Cecilia apart. The movie leads us to believe that the power of their love will prevail when the two are reunited years later, but this turns out to be a fabrication of Briony's guilt. Sadly, Robbie and Cecilia's few moments of romantic bliss are all they can hold onto as the horrors of war deny them from being together.

#17: “Eternal Sunshine of the Spotless Mind” (2004)

This science fiction romance drama comes with the twist of primarily taking place in the protagonist's mind. After realizing his ex-girlfriend Clementine has wiped all memories of him from her mind, an embittered Joel decides to do the same. However, he revisits all the good times before they're deleted, making him realize that he wants to hang onto these memories even if they're painful. The story is ultimately about two people's inability to move on despite knowing they don't work, as they keep hoping not to repeat past mistakes.Although Joel and Clementine find each other once again in the end, it's implied that they might be destined to repeat the cycle of breakups for the rest of their lives.

#16: “Me Before You” (2016)

After an accident leaves him paralyzed below the neck, Will Traynor becomes a cold and cynical person who's unwilling to live. It's after he meets his new caregiver Lou that Will begins to regain his former spirit, as he finds her bubbly and cheerful personality hard to resist. Although the two gradually develop feelings for one another, Lou is unable to change Will's decision. Despite their connection being as pure as it can be, this love story is fated for a tragic ending from the moment they fall for each other. A tearjerker from start to finish, the film does the topic of right place, wrong time full justice, as Lou and Will accept being reunited in death rather than in life.

#15: “Gone with the Wind” (1939)

Considered the first major romantic drama, this legendary epic follows Scarlett O'Hara during and after the American civil war, particularly her turbulent romance with Rhett Butler. Her obsession with Ashley Wilkes causes her to overlook Rhett's affections, while his equally stubborn personality makes him unwilling to devote himself completely to love. The intensity of war leads Scarlett and Rhett back to each other frequently over the years, but not even marriage is enough to salvage their relationship. With numerous issues like Ashley's reappearance and the death of their daughter causing a rift between the couple, the story doles out challenge after challenge. The movie famously ends on Scarlett's late realization of her feelings for Rhett, as he decides their relationship was never meant to last.

#14: “Her” (2013)

Depicting a human-A.I. love story, “Her” follows Theodore, a man crippled by extreme loneliness. After befriending his virtual assistant Samantha, Theodore learns that her growing feelings for him are enabling her to achieve sentience. The emotional depth in Samantha and Theodore's love is driven by the comfort found in companionship, as their dynamic blossoms into romance. At its heart, however, “Her” is about Theodore's inability to overcome depression at losing his ex-wife, as he seeks solace with an A.I. he can never truly be with. This tragically comes to pass when Samantha's evolution doesn't allow her to limit herself to one love. Still, "Her" does leave us on a hopeful note as Theodore learns to move on.

#13: “P.S. I Love You” (2007)

In a change from the norm, this story starts off with the love interests separated, as Holly mourns the death of her husband Gerry. This changes once she starts receiving prearranged messages from Gerry that send her on numerous adventures, as Holly regains her will to live by completing his requests from beyond the grave. Although this sets her on the path to recovery, each message is heart wrenching to see as Holly holds on to whatever semblance she can find of Gerry. The film also flashes back to their marriage, paralleling Holly’s life from back then to where she is now. To its credit, “PS I Love You” does see Holly moving on, although the void of Gerry’s absence always remains.

#12: “Moulin Rouge!” (2001)

An epic musical romance during the end of the 19th century, "Moulin Rouge" deals with the theme of forbidden love. Show writer Christian's love for performer Satine is hindered by the constant interference of the financier, the Duke. Their clandestine love is set in the backdrop of the show's preparation, filled with songs where they confess their love for one another. However, the twist of Satine's terminal illness is a permanent setback for the couple, as their love is cut short without any chance of truly being together. The sad aspect of the movie is bolstered by the musical performances of the lead actors, with Satine and Christian's inner pain fully bared for us to experience.

#11: “The Fault in Our Stars” (2014)

Teen-based romantic dramas rarely have a happy ending and this one follows the same arc. Shailene Woodley and Ansel Elgort play Hazel and Gus, two teenagers suffering from cancer who meet at a support group. Their interests align when they seek out novelist Peter Van Houten to learn the ending of his book, with the two falling in love over the course of their shared experiences. Filled with grand declarations of love and sweet moments, the movie gives us hope for the pair, only for it to end in tragedy. The story is largely about Hazel learning to appreciate the life she has through Gus, whose own impending demise denies them the chance of being together.

#10: “A Walk to Remember” (2002)

This is the first, but certainly not the last film on this list based on a Nicholas Sparks novel. This guy has been creating tearjerkers that make us ugly cry in movie theatres for years. In this coming of age romance, bad boy Landon falls for Jamie, the puritanical reverend's daughter, but he finds out that she has a terminal illness. The relationship between these two was every teenage girl’s dream, especially as Landon helps Jamie cross off every item on her bucket list. If only every high school boyfriend was as kindhearted and adorable as this guy, and every romance was as real as this one.

#9: “The Way We Were” (1973)

Anyone under the age of 30 probably only knows this movie because of the “Sex and the City” episode that references it. But trust us– it’s considered to be a classic for a reason. In this story where total opposites attract, Katie, a radical communist, and Hubbell, a preppy WASP, meet in college and reunite years later. Anyone who’s been in a relationship that is just doomed to fail can relate to this one. Hubbell ends up cheating on Katie while she’s pregnant with his baby– not cool, Hubbell–and in the end, the two go their separate ways. Pretty much every girl aspires to be as cool as Katie was when she runs into Hubbell after they’ve broken up.

#8: “Blue Valentine” (2010)

A word of advice: do NOT watch this movie with your significant other. The trailer might look cute, but this may be one of the most deeply depressing movies ever made, and it’ll make you question whether any relationship can actually work. The story flashes back from past to present, showing both the romantic beginnings of Dean and Cindy’s relationship and the thoroughly heartbreaking state of their marriage five years later. How much could have possibly gone wrong in only five years you ask? You’ll have to watch it to find out.

#7: “Ghost” (1990)

Featuring what is hands down the sexiest pottery scene in film, “Ghost” is undeniably a classic. In this romantic fantasy, Patrick Swayze plays a banker who is very much in love with artist Molly, played by Demi Moore. After Swayze’s character is murdered, he finds himself trapped as a ghost and realizes that his murder was part of a larger plot– and that Molly is in danger. When it comes to romance between a ghost and non-ghost character, the title of “saddest moment” is probably the final scene of the film. That dance was definitely a heartbreaker, but watching Sam walk into the light gets us every time.

#6: “The Bridges of Madison County” (1995)

In what is possibly everyone’s mom’s favorite movie, an Iowa housewife’s life is turned upside-down by a brief, but passionate, affair. Francesca’s family is away for the week when National Geographic photographer Robert Kincaid happens upon her home to ask for directions. They end up spending four blissful days together, but in the end, she makes the responsible choice to stay with her husband. As her children are going through her possessions after her death, they realize that the relationship stayed with her until her dying days. Watching Francesca almost change her mind and get into the car with Robert is especially excruciating to witness.

#5: “Romeo + Juliet” (1996)

The classic tale of star-crossed lovers is adapted for a modern audience by Baz Luhrmann in this film starring Leonardo DiCaprio and Claire Danes. Shakespeare’s original dialogue remains, but the setting changes to the fantastical modern city of Verona Beach. Even if you didn’t really get it when you read the play in high school, this movie is undeniably romantic. To make the tragic ending even more tragic, in this version of the well-known story, rather than waking to find an already dead Romeo, Juliet opens her eyes just in time to see him take his own life. There are plenty of film adaptations of “Romeo + Juliet” out there, but no one does doomed love affairs quite like Baz.

#4: “Casablanca” (1942)

Here’s lookin’ at you, kids. This Academy Award-winning film is widely considered one of the greatest movies ever made and one of Hollywood’s best love stories. Humphrey Bogart and Ingrid Bergman star in this time-honored wartime drama, playing Rick and Ilsa, former lovers reunited in Morocco. Even though Ilsa has since gotten married, the two plan to run off together. Casablanca was released in the midst of World War II when audiences were looking for something uplifting to see at the theater, but unfortunately, there’s no happy ending here as the lovers go their separate ways in the well-known final scene.

#3: “Brokeback Mountain” (2005)

We just can’t quit these two. This poignant movie tells the story of two men who meet when both are hired to herd sheep in Wyoming during the early 1960s. Things get complicated when they develop a romantic relationship, which–considering the time period– is completely taboo. There are a lot of sad moments here, as we see both Jack and Ennis marry women, have children, and try to continue on with their lives. They meet every few years, but know that it would be impossible for them to ever truly be together. We wish they could’ve gotten the happily ever after they deserved, but no such luck. We’ll just sit here rewatching that final scene, quietly sobbing.

#2: “The Notebook” (2004)

Nicholas Sparks strikes again in what is probably the most well-known of the films based on his books. Although “Dear John” is another tragic, memorable adaptation, “The Notebook” has got it all - a timeless plot, a passionate romance, and the Ryan Gosling factor. Love it or hate it, you can’t deny that this is a pretty adorable love story. As much as we relish in watching the scenes featuring young Noah and Allie, the part that moves us most is when they’re in the retirement home, and Allie suddenly remembers that the story Noah has been telling is actually about them. If you don’t cry when old Noah cries, then you’re most likely some sort of heartless monster.

#1: “Titanic” (1997)

As if it could have been any other movie! “Titanic” is the spectacular, epic romance that all other love stories will be measured up against for years to come. It’s got everything a great tragic romance movie needs: lovers from different social classes, period costumes, life threatening situations, steamy car scenes, and a whole lot more. We really would have loved to see Rose and Jack’s relationship progress post-sinking, but alas, it wasn’t meant to be. We’re pretty sure that two people could have fit on that floating door, but regardless, when Rose finally sees Jack again in her dreams we can’t help but shed a tear. We’ll never let go either, Jack.