Most Heartbreaking Films Ever

Saddest films I've ever seen. Don't get me wrong; they're all superb, well made, and well acted, but tragic beyond belief. Be ready to be crushed. No particular order, just the order in which I thought of them.
View:
Log in to copy items to your own lists.
1.
The Green Mile (1999)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
The lives of guards on Death Row are affected by one of their charges: a black man accused of child murder and rape, yet who has a mysterious gift. (189 mins.)
Director: Frank Darabont
 
2.
The Road (2009)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
In a dangerous post-apocalyptic world, an ailing father defends his son as they slowly travel to the sea. (111 mins.)
Director: John Hillcoat
 
3.
Revolutionary Road (2008)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A young couple living in a Connecticut suburb during the mid-1950s struggle to come to terms with their personal problems while trying to raise their two children. (119 mins.)
Director: Sam Mendes
 
4.
Terms of Endearment (1983)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Follows hard-to-please Aurora looking for love and her daughter's family problems. (132 mins.)
Director: James L. Brooks
 
5.
Schindler's List (1993)
    1 2 3 4 5 6 7 8 9 10 8.9/10 X  
In German-occupied Poland during World War II, Oskar Schindler gradually becomes concerned for his Jewish workforce after witnessing their persecution by the Nazi Germans. (195 mins.)
 
6.
Chinatown (1974)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A private detective hired to expose an adulterer finds himself caught up in a web of deceit, corruption and murder. (130 mins.)
Director: Roman Polanski
 
7.
Leaving Las Vegas (1995)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Ben Sanderson, an alcoholic Hollywood screenwriter who lost everything because of his drinking, arrives in Las Vegas to drink himself to death. There, he meets and forms an uneasy friendship and non-interference pact with prostitute Sera. (111 mins.)
Director: Mike Figgis
 
8.
The Boy in the Striped Pajamas (2008)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Set during WWII, a story seen through the innocent eyes of Bruno, the eight-year-old son of the commandant at a German concentration camp, whose forbidden friendship with a Jewish boy on the other side of the camp fence has startling and unexpected consequences. (94 mins.)
Director: Mark Herman
 
9.
About Schmidt (2002)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A man upon retirement embarks on a journey to his estranged daughter's wedding only to discover more about himself and life than he ever expected. (125 mins.)
Director: Alexander Payne
 
10.
Million Dollar Baby (2004)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A determined woman works with a hardened boxing trainer to become a professional. (132 mins.)
Director: Clint Eastwood
 
11.
The Descendants (2011)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A land baron tries to reconnect with his two daughters after his wife is seriously injured in a boating accident. (115 mins.)
Director: Alexander Payne
 
12.
Ordinary People (1980)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
The accidental death of the older son of an affluent family deeply strains the relationships among the bitter mother, the good-natured father, and the guilt-ridden younger son. (124 mins.)
Director: Robert Redford
 
13.
Titanic (1997)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A seventeen-year-old aristocrat falls in love with a kind but poor artist aboard the luxurious, ill-fated R.M.S. Titanic. (194 mins.)
Director: James Cameron
 
14.
In the Bedroom (2001)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
A New England couple's college-aged son dates an older woman who has two small children and an unwelcome ex-husband. (130 mins.)
Director: Todd Field
 
15.
Sophie's Choice (1982)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
After spending time with his new neighbors, an aspiring writer realizes they are harboring deep secrets that will forever change him. (150 mins.)
Director: Alan J. Pakula
 
16.
Atonement (2007)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Fledgling writer Briony Tallis, as a thirteen-year-old, irrevocably changes the course of several lives when she accuses her older sister's lover of a crime he did not commit. (123 mins.)
Director: Joe Wright
 
17.
Shame (2011)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
In New York City, Brandon's carefully cultivated private life - which allows him to indulge his sexual addiction - is disrupted when his sister arrives unannounced for an indefinite stay. (101 mins.)
Director: Steve McQueen
 
18.
Last Tango in Paris (1972)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A young Parisian woman meets a middle-aged American businessman who demands their clandestine relationship be based only on sex. (129 mins.)
 
19.
Requiem for a Dream (2000)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
The drug-induced utopias of four Coney Island people are shattered when their addictions run deep. (102 mins.)
 
20.
Meet Joe Black (1998)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
Death, who takes the form of a young man, asks a media mogul to act as a guide to teach him about life on Earth and in the process he falls in love with his guide's daughter. (178 mins.)
Director: Martin Brest
 
21.
Grave of the Fireflies (1988)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
A young boy and his little sister struggle to survive in Japan during World War II. (89 mins.)
Director: Isao Takahata
 
22.
Dancer in the Dark (2000)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
An east European girl goes to America with her young son, expecting it to be like a Hollywood film. (140 mins.)
Director: Lars Von Trier
 
23.
The Wrestler (2008)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
A faded professional wrestler must retire, but finds his quest for a new life outside the ring a dispiriting struggle. (109 mins.)
 
24.
12 Years a Slave (2013)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
In the antebellum United States, Solomon Northup, a free black man from upstate New York, is abducted and sold into slavery. (134 mins.)
Director: Steve McQueen
 
25.
Fruitvale Station (2013)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
The story of Oscar Grant III, a 22-year-old Bay Area resident, who crosses paths with friends, enemies, family, and strangers on the last day of 2008. (85 mins.)
Director: Ryan Coogler
 
26.
Lost and Delirious (2001)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A newcomer to a posh girls boarding school discovers that her two senior roommates are lovers. (103 mins.)
Director: Léa Pool
 
27.
The Fault in Our Stars (2014)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Two teenage cancer patients begin a life-affirming journey to visit a reclusive author in Amsterdam. (126 mins.)
Director: Josh Boone
 
28.
Brian's Song (1971 TV Movie)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Based on the real-life relationship between teammates Brian Piccolo and Gale Sayers and the bond established when Piccolo discovers that he is dying. (73 mins.)
Director: Buzz Kulik