100 Saddest Movies of All Time

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Source: Courtesy of Fox Searchlight Pictures

11. Boys Don’t Cry (1999)
> Directed by: Kimberly Peirce
> Starring: Hilary Swank, Chloë Sevigny, Peter Sarsgaard

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 Columbia Pictures Corporation

12. Boyz n the Hood (1991)
> Directed by: John Singleton
> Starring: Cuba Gooding Jr., Laurence Fishburne, Hudhail Al-Amir

Three young black men take different paths out of South Central Los Angeles in this gritty evocation of West Coast ghetto life. When one of them, about to go to USC on an athletic scholarship, is killed by Crips gang members, the other two and another friend set out to avenge his death. One bows out of the mission, but the other two follow through. One is killed two weeks later, raising the question of whether there is a way out of South Central’s cycle of violence.

Source: Courtesy of October Films

13. Breaking the Waves (1996)
> Directed by: Lars von Trier
> Starring: Emily Watson, Stellan Skarsgård, Katrin Cartlidge

The life of a couple in a rural Scottish village in the 1970s is shattered when the husband is paralyzed in an oil rig accident. Unable to perform sexually, he asks his wife to take lovers and tell him about her experiences. At first she refuses, but then becomes convinced that her actions will somehow cure her mate. As her indiscretions become known in the village, she is ostracized and eventually killed. Her husband miraculously recovers, and when she is refused a Christian burial, he steals the body and buries her at sea.

Source: Courtesy of Miramax

14. Cinema Paradiso (1988)
> Directed by: Giuseppe Tornatore
> Starring: Philippe Noiret, Enzo Cannavale, Antonella Attili

Told mostly in flashback, this is the story of a young boy in a Sicilian village who loves movies and spends hours watching them from the projection booth of the local theatre with the kindly projectionist. When a fire leaves the man blind, the boy takes over his duties. The boy grows up and falls in love with a local girl, but after the girl’s father intervenes on the budding relationship, the boy joins the army and leaves town for good. Years later, having become a famous director himself, he returns for his mentor’s funeral.

Source: Courtesy of Focus Features

15. Dallas Buyers Club (2013)
> Directed by: Jean-Marc Vallée
> Starring: Matthew McConaughey, Jennifer Garner, Jared Leto

“Dallas Buyers Club” is a biographical film based on the life of Ron Woodroof, an AIDS patient who smuggled unapproved experimental drugs into Texas during the 1980s. While Woodroof’s actions begin primarily as a means of making money, his compassion for other patients grows even as his own health deteriorates.

Source: Courtesy of Fine Line Features

16. Dancer in the Dark (2000)
> 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.

Source: Courtesy of Paramount Pictures

17. Days of Heaven (1978)
> Directed by: Terrence Malick
> Starring: Richard Gere, Brooke Adams, Sam Shepard

Set in the Texas Panhandle before World War I, this beautifully photographed movie is about a fugitive man, his girlfriend, and his kid sister who find work on a farm and hatch a plot of inherit the wealthy farmer’s money. The farmer and the fugitive die at the end and the sisters go their separate ways.

Source: Courtesy of Gramercy Pictures

18. Dead Man Walking (1995)
> Directed by: Tim Robbins
> Starring: Susan Sarandon, Sean Penn, Robert Prosky

A nun befriends a convicted murderer on Death Row shortly before his execution, even as she empathizes with the families of the victims. Attempts to win the killer a stay of execution fail, but she helps him accept responsibility for his crimes, and rests her hand on his shoulder as he walks his last mile.

Source: Courtesy of Buena Vista Pictures Distribution

19. Dead Poets Society (1989)
> Directed by: Peter Weir
> Starring: Robin Williams, Robert Sean Leonard, Ethan Hawke

Social and educational dynamics at a private boys’ school in New England in the 1950s provide the setting for this elegiac and inspiring Robin Williams vehicle. An unorthodox teacher (Williams), a resurrected secret society, a martinet father, and a school play lead up to a tragic suicide and the teacher’s dismissal.

Source: Courtesy of Focus Features

20. Eternal Sunshine of the Spotless Mind (2004)
> Directed by: Michel Gondry
> Starring: Jim Carrey, Kate Winslet, Tom Wilkinson

“Eternal Sunshine of the Spotless Mind” stands out from other films thanks to its relentless creativity, driven by the film’s director Michel Gondry and co-writer Charlie Kaufman. The clever direction and original screenwriting help highlight a story of heartbreak, in which two former lovers attempt to remove all memories of their failed relationship.