Everyone likes movies with happy endings, but sometimes filmmakers throw a curveball into the mix and turn moments that seem like they’re headed for a happy conclusion into something much sadder. This often leads to bittersweet endings that may not make you feel warm and fuzzy, but which nevertheless stick in your memory and get you in an existential frame of mind. Whether it’s a heart-wrenching goodbye that you didn’t see coming or a character realizing they’ve outgrown their dreams, these moments conjure complex emotions that go beyond the binary of happy and sad.
Movie moments that should have been happy but turn out to be heartbreaking pop up in every genre, from lighthearted kid’s animation to the MCU to Oscar-winning dramas. Keep reading to see which movies refused to let their characters (and audiences) bask in the uplifting moment they were expecting, and vote up the ones that hurt the most to watch.
Shawshank Prison is a brutal place full of sadistic guards, violent inmates, and a pervasive sense of hopelessness, but not all the inhabitants want to leave. Brooks (James Whitmore) is one of them. He’s been in prison for 50 years and is now an old man with no understanding of the rapidly evolving outside world. For most men in the prison, being granted parole would be the happiest day of their lives, but for him, it’s the beginning of the end.
When Brooks is released from prison, he writes a letter to his friends at Shawshank, remarking that things have changed drastically since he went inside and that the world has “got itself into a big hurry.” He rides the bus, clinging to the seat in front of him with a fearful look in his eye. He packs groceries despite the pain in his hands, wanders the streets looking lost, and is nearly hit by a car when he forgets to look before crossing the road. He takes up lodging at a halfway house, but writes to his friends that he doesn’t like the outside world. He confesses that he thinks about buying a gun and robbing the grocery store where he works so that they’ll “send [him] home,” but decides he’s too old to commit crimes anymore. “I don’t like it here,” he writes, “I’m tired of being afraid all the time. I’ve decided not to stay.” Despite being “free,” he can’t handle his new life and decides to end it, carving “Brooks was here” into the wooden beams in his room before ending his own life. It’s a bleak ending to what should be a new lease on life, and underscores the complicated relationship that the inmates in the movie have with prison.
Chuck Noland (Tom Hanks) is stranded on an isolated island after a plane crash. For four harrowing years, he keeps himself sane with the help of a volleyball named Wilson and a pocket watch with a picture of his girlfriend, Kelly (Helen Hunt). Even though he has little chance of returning home, he maintains the will to live by dreaming of seeing her again. When he is miraculously rescued by a passing ship, his prayers are answered, but his reunion with Kelly is much more complicated than he might have hoped. For one thing, she’s married and has children. For another, the emotional toll of losing Chuck and processing his presumed death has forced her to distance herself from him in a way that proximity can’t heal.
When they finally see each other again, it’s at her home. She gives him the keys to his old Jeep that she’s been holding onto and he begins to drive away. Suddenly, she chases after him, and, like the show-stopping, rain-drenched kisses in The Notebook and Four Weddings and a Funeral, they passionately embrace and confess their undying love for each other. This could be the final scene, implying that the couple ends up together, despite everything. But they pull away, and Chuck tells her that she needs to go home. Their reunion could have been the beginning of a new life together, but instead, it underscores the unfathomable distance that has fallen between them since Chuck’s disappearance. The scene is all the more tragic because Kelly tells him he will always be the love of her life. Cast Away is mostly a one-man movie about isolation and resilience, but the reunion between the couple rivals Titanic and Brokeback Mountain for heartbreaking romantic endings.
Sequels to beloved movies rarely live up to their predecessors, but Pixar managed to land several heartwarming sequels to Toy Story by embracing the passage of time. In Toy Story 3, Andy is college-bound and no longer plays with Buzz, Woody, or any of his other childhood toys. As he packs to move out of the house, he puts the toys into a plastic bag, intending to store them in the attic. By the end of the movie, however, he decides to give them to Bonnie, one of the kids in the neighborhood who he knows will love the toys as much as he did at her age. It’s a heartwarming moment, but it takes a heartbreaking turn.
As Andy introduces the toys to Bonnie, he lovingly describes each of them one by one. At last, he comes to Woody who he intended to take with him to college. He snatches the toy from Bonnie, unable to part with him, but relents when he sees the confusion in her eyes. He tells her that Woody has been his pal for as long as he can remember and that he’ll be there for her no matter what. As he gets in his car to leave, Andy gives the toys one last look, and whispers, “Thanks, guys.” As he drives away, Woody says, “So long, partner.” It will rip your heart out.
Kathryn Bigelow’s 2008 Oscar-winner The Hurt Locker stars Jeremy Renner as Staff Sgt. William James, the hot-headed leader of an Army explosive ordnance disposal team in Iraq. His reckless approach to the job alienates him from his colleagues and has violent consequences. When their deployment finally ends, his fellow sergeant tells him that he can no longer cope with the dangers and stresses of the job and is ready to go back to civilian life and start a family. For James, however, the return home is more complicated.
During a trip to the grocery store with his wife and infant son, James is visibly detached. Standing in the cereal aisle, he surveys the choices, turning his head in one direction and then the other, the rows of boxes stretching as far as the eye can see. He grabs a box in front of him, throws it into his cart, and strides down the aisle, whacking the shelves as he leaves. Despite being calm when faced with a live bomb in the center of a deadly conflict, his frustration at the overwhelming number of cereal choices demonstrates his inability to reintegrate into normal life or enjoy the safety and stability of home. Not long after his grocery store outing, he chooses to return to Iraq for another deployment, confiding to his infant son that his work is the only thing he really loves.
Meeting your heroes doesn’t always go the way you think it will, and in Pixar’s 2009 movie Up, Carl (Ed Asner) learns this the hard way. Having idolized the legendary explorer Charles Muntz since childhood, Carl finally decides to journey to Muntz’s last known location, Paradise Falls in South America, where his late wife had wanted to live. Condemned to a nursing home, Carl escapes by tying thousands of balloons to his house and floating his way to South America, begrudgingly taking 8-year-old Russell along for the ride. Despite life-threatening conditions, they reach Paradise Falls and encounter an elderly Muntz. He invites the travelers into his elaborately decorated aircraft where he’s spent the past few decades trying to piece together the skeleton of an elusive, possibly non-existent bird. It’s Carl’s dream come true, until it isn’t.
During their visit, Muntz reveals he’s attacked and killed several other travelers over the years, believing they were trying to discover the bird before he could. He shows Carl and Russell a shelf of helmets, ticking off each instance of an unwanted guest who he dealt with. When Russell mentions they saw a bird that looks like the skeleton Muntz has reconstructed, the elderly explorer turns on them and things go downhill from there. He sets his dogs on them, traps the bird, and sets Carl’s house on fire. It’s an exceedingly ugly outcome to an encounter that should have been the happy culmination of Carl’s lifelong dream.
Rick Blaine (Humphrey Bogart) is a world-weary American running a popular nightclub in Vichy-occupied Morocco during World War II. He stays out of politics and “sticks his neck out for no one.” All of that changes, however, when his old flame Ilsa (Ingrid Bergman) arrives in Casablanca with her husband Laszlo, a leader in the French Resistance. Rick and Ilsa still harbor feelings for each other, and he has to decide whether to take a stance on the war by helping Laszlo escape to America or maintain his self-preserving neutrality. He chooses the former, demonstrating a renewed faith in humanity and his willingness to put himself on the line for a higher cause, but his decision has other consequences.
Standing in the swirling fog near the plane that’s set to fly Laszlo to safety, Rick shocks Ilsa by announcing she must accompany her husband instead of staying with him. She protests, but he tells her that “nine chances out ten” they would both end up in a concentration camp if she stayed. By helping Laszlo, he’s risking his life, and because he loves Ilsa, he’s unwilling to let her face similar consequences just to be with him. Instead of the romantic future they had agreed upon the night before, Rick and Ilsa part ways in one of the saddest movie endings of all time.
