The Saddest Movies of All Time

From director Ang Lee comes this acclaimed drama, which captures an ensemble cast at the top of its game. The story follows two upper-middle-class families as they explore taboo behavior in early 1970s Connecticut. It “captures this place, this season, this garish and confused moment in history, with surgical precision,” wrote critic David Ansen for Newsweek.

A high school student is assigned to write a paper about his older brother, a former neo-Nazi leader, and becomes involved with white supremacists himself. Both eventually repent, but after he turns in his paper, the younger brother is killed by a black student, leaving his older sibling to mourn.

A young transgender man falls in love with a woman who is unconcerned with his sexual identity. The woman’s unenlightened male friends beat and rape the man. Later, they get drunk and decide to kill him, which they do despite his lover’s pleas.

Set in the 1930s, this sprawling drama centers on the lives of Death Row guards at a Southern penitentiary. With the introduction of convicted murderer John Coffey (Michael Clarke Duncan) comes a story of injustice, tragedy, magic, and redemption. It’s all based on Stephen King’s serialized novel of the same name.

This heart-tugging tale, set in Washington state in 1964, stars the Icelandic pop star Björk as a musical-loving Czech immigrant who is slowly going blind from a genetic condition. As she desperately tries to save money for an operation that will prevent her young son from suffering the same fate, she periodically breaks into song and dance. Her cop neighbor, himself in need of funds, steals from her, leading to a deadly confrontation.