The Saddest Movies of All Time

This Gus Van Sant drama centers on the romance between a terminally ill girl (Mia Wasikowska) and death-obsessed boy (Henry Hopper). Coping with tragedy provides for an overarching motif.

This French tear-jerker is about two former musicians and piano teachers, husband and wife, both in their 80s. One morning, the woman has a stroke and ends up partially paralyzed. When she gets out of the hospital, her husband promises she will never go back, and when he can no longer care for her, he tells her a story, then smothers her. He covers her body with flowers and seals the room she’s in, then imagines her washing dishes in the kitchen.

A young girl gets stuck in the middle of a bitter custody battle between two self-absorbed parents in this searing drama. As the saga unfolds, it causes potentially irreversible damage to her psychological development. Onata Aprile gives a knockout performance as Maisie.

Based on an 1853 memoir by a free black man from Saratoga, New York, who was kidnapped and sold into slavery, this film convincingly evokes the cruelty of plantation life, but it also pays tribute to the resilience of the enslaved. Though the story ends with the hero returned to his home and family, he has lost 12 years of his life and missed seeing his children grow into adults.

In the near future, a lonely introvert going through a divorce buys an operating system with artificial intelligence, gives her a female identity, and falls in love with her. She apparently reciprocates. All goes well until she tells him that she interacts with thousands of other people, too, and is in love with 641 of them. She then tells him that she and other similar operating systems have evolved beyond humanity, and leaves for another plane of being.