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The top 10 saddest and most depressing movies ever made.

B. Hollendonner "Chiend"
 
Requiem for a Dream (Director's Cut)
Requiem for a Dream (Director's Cut)
"Examination of drug addiction between a mother, her son, and his two friends.  Begins as a heavy comedy until their lives spiral out of control. Just when things couldn't get worse for them, it does."
They Shoot Horses, Don't They?
They Shoot Horses, Don't They?
"Outstanding film depicting the cruelty of the dance marathons during the great depression.  Jane Fonda's performance is truly heart-rending."
I Stand Alone
I Stand Alone
"A man leaves prison feeling he has nothing left to look forward to. One scene has him turned down for a job in a butcher shop because he is unable to smile.  A man truly at the end of his rope."
The Pawnbroker - 30th Anniversary Edition [VHS]
The Pawnbroker - 30th Anniversary Edition [VHS]
"Rod Steiger is Sol Nazerman, a pawnbroker haunted by memories of a Nazi concentration camp and the destruction of his once-happy family. A truly terrifying story."
Eraserhead
Eraserhead
"A grim, nightmarishly surreal oddity that defies description. Definitely one of the most downbeat films ever committed to celuloid."
The Deer Hunter
The Deer Hunter
"A story of three friends from a small Pennsylvania steel town torn apart by the Vietnam war. A heartbreaking film to the end."
Jacknife [VHS]
Jacknife [VHS]
"Robert DeNiro visits army buddy Ed Harris (who is suffering from depression) and tries to help him sort out his past.  I can't watch this film without falling apart emotionally."
The Music Lovers [VHS]
The Music Lovers [VHS]
"A Ken Russell film about Peter Ilich Tchaikovsky and his struggle to deal with his own homosexual guilt and his marriage to the nymphomaniac Nina.  Has an unbelievably miserable ending."
Ikiru (The Criterion Collection)
Ikiru (The Criterion Collection)
"Simple story of a retired public servant dying of cancer and his dream to bring an ounce of meaning to his wasted life by turning a dump into a playground.  The conclusion will infuriate you."
La Strada (The Criterion Collection)
La Strada (The Criterion Collection)
"Circus strongman Anthony Quinn takes in a simple-minded waif to assist him in his roadside shows and treats her with cruelty and indifference.  Guaranteed to ruin your day."