The Saddest Movies of All Time

Source: Courtesy of Twentieth Century Fox

The Ice Storm (1997)
> IMDb rating: 7.4 / 10
> Tomatometer score: 85%
> RT audience score: 82%
> Directed by: Ang Lee
> Starring: Kevin Kline, Joan Allen, Sigourney Weaver, Henry Czerny

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.

Source: Courtesy of New Line Cinema

American History X (1998)
> IMDb rating: 8.5 / 10
> Tomatometer score: 83%
> RT audience score: 96%
> Directed by: Tony Kaye
> Starring: Edward Norton, Edward Furlong, Beverly D’Angelo, Jennifer Lien

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.

Source: Courtesy of Fox Searchlight Pictures

Boys Don’t Cry (1999)
> IMDb rating: 7.5 / 10
> Tomatometer score: 89%
> RT audience score: 87%
> Directed by: Kimberly Peirce
> Starring: Hilary Swank, Chloe Sevigny, Peter Sarsgaard, Brendan Sexton III

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.

Source: Courtesy of Warner Bros.

The Green Mile (1999)
> IMDb rating: 8.6 / 10
> Tomatometer score: 78%
> RT audience score: 94%
> Directed by: Frank Darabont
> Starring: Tom Hanks, Michael Clarke Duncan, David Morse, Bonnie Hunt

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.

Source: Courtesy of Fine Line Features

Dancer in the Dark (2000)
> IMDb rating: 7.9 / 10
> Tomatometer score: 69%
> RT audience score: 91%
> Directed by: Lars von Trier
> Starring: Björk, Catherine Deneuve, David Morse

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.

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