Special Report

100 Saddest Movies of All Time

Source: Courtesy of Trans Lux

41. La Strada (1954)
> Directed by: Federico Fellini
> Starring: Anthony Quinn, Giulietta Masina, Richard Basehart

In this 1950s Fellini classic, a naive young girl living in poverty is sold by her mother into servitude to a sideshow strongman. The Fool, a circus fiddler and high-wire acrobat, convinces the girl to stay with the strongman, despite his cruelty to her. But the Fool also pokes fun at the brute, and he responds by beating the man to death. He then abandons the girl, leaving her to die in the snow.

Source: Courtesy of TriStar Pictures

42. Legends of the Fall (1994)
> Directed by: Edward Zwick
> Starring: Brad Pitt, Anthony Hopkins, Aidan Quinn

Based on one of the best-known of author Jim Harrison’s works — and considered the film that made Brad Pitt a star — this is the tale of an army colonel raising three sons in rural Montana in the early 1900s. As time goes by, one son goes east to Harvard and returns with a beautiful fiancée. All three brothers go off to fight in World War I and the Harvard graduate is killed. One of his brothers proposes to the woman in his place but is rebuffed, and she and the remaining brother become lovers. He marries another woman, however, driving the abandoned woman to suicide.

Source: Courtesy of Miramax

43. Life Is Beautiful (1997)
> Directed by: Roberto Benigni
> Starring: Roberto Benigni, Nicoletta Braschi, Giorgio Cantarini

When an Italian Jewish poet and his young son are arrested by the Nazis and sent to a concentration camp, the man tells his son that they’re on vacation and tries to turn the whole experience into a game. The youngster survives; his father does not. A critic for Entertainment Weekly called it “the first feel-good Holocaust weepie.”

Source: Courtesy of Newmarket Films

44. Lilya 4-Ever (2002)
> Directed by: Lukas Moodysson
> Starring: Oksana Akinshina, Artyom Bogucharskiy, Pavel Ponomaryov

Abandoned by her mother, a teenage girl in a former Soviet republic turns to prostitution in her hometown. She befriends a young man whose father abuses him, and she buys him a basketball with her earnings. Another man, who becomes her boyfriend, offers her a job in Sweden. There, she is imprisoned by a pimp and raped by him and his customers. Back home, her friend kills himself. Beaten by her pimp and saddened by her friend’s death, she commits suicide too. The film ends with her and her friend as angels, playing basketball on a rooftop.

Source: Courtesy of Paramount Pictures

45. Love Story (1970)
> Directed by: Arthur Hiller
> Starring: Ali MacGraw, Ryan O’Neal, John Marley

Wealthy Harvard student meets working-class Radcliffe girl. Rich kid’s father disinherits him when he takes up with her and they get married. Couple struggles along while Harvard guy finishes law school. He gets a good job in New York and the two try to have a baby. He learns that his wife is fatally ill with cancer (or maybe leukemia). She doesn’t know, but she eventually finds out. She dies. Rich guy’s dad apologizes to him. Rich guy replies with one of the most saccharine slogans of the seventies: “Love means never having to say you’re sorry.”

Source: Courtesy of Roadside Attractions

46. Manchester by the Sea (2016)
> Directed by: Kenneth Lonergan
> Starring: Casey Affleck, Michelle Williams, Kyle Chandler

Actors Matt Damon and John Krasinski were among the producers of this family drama, and came up with the original idea for the story. A troubled Boston apartment handyman learns that his brother has died suddenly in the nearby seaside town where both men grew up, and that he is now the guardian of his brother’s 16-year-old son. The handyman struggles to connect with the boy, and with his own ex-wife.

Source: Courtesy of IFC Films

47. Mary and Max (2009)
> Directed by: Adam Elliot
> Starring: Toni Collette, Philip Seymour Hoffman, Eric Bana

“Mary and Max” is an Australian stop motion animation film that may be equal parts funny and sad. Detailing the relationship between two pen pals – young Australian girl Mary and older American Max – the film illustrates the powers of friendship and forgiveness in such a way that is uncommon to many animated films.

Source: Courtesy of Palm Pictures

48. Memories of Murder (2003)
> Directed by: Joon-ho Bong
> Starring: Kang-ho Song, Sang-kyung Kim, Roe-ha Kim

This dark crime drama is based on the true story of serial murders in South Korea, committed in the countryside in the 1980s. The main character, a police detective sent from Seoul to help solve the case, is a troubled man, held in check by a less experienced local cop. The murders are never solved, but the local man remains haunted by them.

Source: Courtesy of Focus Features

49. Milk (2008)
> Directed by: Gus Van Sant
> Starring: Sean Penn, Josh Brolin, Emile Hirsch

“Milk” is the second film on our list directed by Gus Van Sant, after “Good Will Hunting.” Unlike the latter film, “Milk” is a true story, based on the life of gay rights activist and San Francisco politician Harvey Milk. While the majority of the film covers Milk’s political rise and accomplishments, the tragic conclusion leaves a dark cloud over all that came before.

Source: Courtesy of Warner Bros.

50. Million Dollar Baby (2004)
> Directed by: Clint Eastwood
> Starring: Hilary Swank, Clint Eastwood, Morgan Freeman

An impoverished, cantankerous 31-year-old waitress is determined to become a boxer, and she finds a boxing gym owner to take her on and train her. The two develop a surrogate father-daughter relationship as she hones her pugilistic skills. She’s finally ready for a championship fight against the middleweight women’s champion. Her opponent fights dirty, and finally blindsides her, knocking her into a corner stool and leaving her permanently paralyzed. Bedridden and with a leg amputated for gangrenous bed sores, she simply wants to end her life. Her trainer grants her wish.

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