100 Saddest Movies of All Time

Source: Courtesy of Fox Searchlight Pictures

91. Three Billboards Outside Ebbing, Missouri (2017)
> Directed by: Martin McDonagh
> Starring: Frances McDormand, Woody Harrelson, Sam Rockwell

Frustrated by the inability of local authorities to solve the rape and murder of her daughter, a Missouri mother puts up three billboards asking the police chief — who happens to be dying of cancer — why he has made no arrests. Violence, arson, and suicide ensue.

Source: Courtesy of Paramount Pictures

92. Titanic (1997)
> Directed by: James Cameron
> Starring: Leonardo DiCaprio, Kate Winslet, Billy Zane

James Cameron’s “Titanic” was a cultural landmark, winning 11 Academy Awards and becoming the second-highest grossing movie of all time, worldwide — second only to the same director’s “Avatar.” The film was also highly successful at evoking tears from the audience’s eyes, with both the tragic demise of the Titanic itself and the doomed romance between the film’s main characters, Jack and Rose.

Source: Courtesy of Buena Vista Pictures

93. Tuck Everlasting (2002)
> Directed by: Jay Russell
> Starring: Alexis Bledel, Jonathan Jackson, Sissy Spacek

In 1914, a wealthy, well-bred young girl meets and falls in love with a boy from a family of immortals living in the woods near her mansion. A mysterious man in a yellow suit seeks to interrupt the idyll and is killed. The girl has a chance to join her swain in eternal life, but chooses not to, and goes on to lead a normal life, dying at the age of 100.

Source: Courtesy of Janus Films

94. Umberto D. (1952)
> Directed by: Vittorio De Sica
> Starring: Carlo Battisti, Maria Pia Casilio, Lina Gennari

In this film, one of the classics of post-War War II Italian neorealism, an impoverished retired civil servant, whose only friends are his dog and a kitchen maid in his rooming house, is evicted after he falls ill and is unable to raise the money to pay his back rent. Finally, despondent, he takes his dog in his arms and stands in front of an oncoming train.

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Source: Courtesy of New Yorker Films

95. Underground (1995)
> Directed by: Emir Kusturica
> Starring: Predrag ‘Miki’ Manojlovic, Lazar Ristovski, Mirjana Jokovic

From the early days of World War II through the Cold War and into the Yugoslav Wars of the 1990s, two Serbian friends carouse, spy, fight, murder, fall in love, disappear, and reappear. In the surrealistic conclusion, all the characters, living and dead, are reunited for a wedding feast.

Source: Courtesy of Universal Pictures

96. United 93 (2006)
> Directed by: Paul Greengrass
> Starring: David Alan Basche, Olivia Thirlby, Liza Colón-Zayas

This is a fact-based reimagining of the events aboard one of the airliners hijacked by terrorists on 9/11. In this case, heroic passengers attempt to overpower the hijackers, who plan to crash the plane into the U.S. Capitol building in Washington, D.C., and nearly succeed — but the plane goes down anyway in a Pennsylvania field, killing all on board.

Source: Courtesy of Walt Disney Studios Motion Pictures

97. Up (2009)
> Directed by: Pete Docter, Bob Peterson
> Starring: Edward Asner, Jordan Nagai, John Ratzenberger

Pixar – the Disney-owned animation studio behind “Toy Story,” “The Incredibles,” and “Finding Nemo” – is better known for its family-friendly feel-good movies than for anything sad. Nonetheless, with “Up” they produced one of the most moving animated movies of all time, as we watch protagonist Carl Fredricksen falling in love, living life, and finally losing his wife, Ellie. Keeping his promise to her, he turns his house into an airship, hooks up with an eccentric explorer, and ends up where the couple had always dreamed of being.

Source: Courtesy of Sony Pictures Classics

98. Waltz with Bashir (2008)
> Directed by: Ari Folman
> Starring: Ari Folman, Ron Ben-Yishai, Ronny Dayag

In this animated documentary, an Israeli film director, realizing that he remembers nothing about his role in Israel’s 1982 invasion of Lebanon, sets out to interview old friends and colleagues about that period in his life. He comes to realize that he played a role, albeit a peripheral one, in the massacre of Palestinians in the refugee camps of Sabra and Shatila.

Source: Courtesy of Janus Films

99. Wild Strawberries (1957)
> Directed by: Ingmar Bergman
> Starring: Victor Sjöström, Bibi Andersson, Ingrid Thulin

Nostalgia, regret, and guilt are among the strongest emotions known to man. All three are approached without restraint in Ingmar Bergman’s 1957 film “Wild Strawberries.” The movie tells the story of a man nearing the end of his time on earth, looking back on his life in contemplation. According to a review in The Guardian, “what makes the film great is its nearness to each of us.”

Source: Courtesy of Adopt Films

100. Winter Sleep (2014)
> Directed by: Nuri Bilge Ceylan
> Starring: Haluk Bilginer, Melisa Sözen, Demet Akbag

Being based on works by Anton Chekhov and Fyodor Dostoevsky, it’s perhaps not surprising that this Turkish drama wades deep into emotional misery. The film centers around a hotel owner, Aydin, and his relationships with his wife, sister, and others. Slow-paced but engrossing, the film does an excellent job of exploring the emotional core of the human condition.