55 Most Depressing Movies Ever! (in no particular order)

This is a venture into the cinematic depression. The list, however, was compiled in haste. So please feel free to suggest any edits/additions.

Warning: please avoid watching if you are carrying or are seriously psychologically/mentally ill. Thank you.

Movies listed below are in no particular order.
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1.
Shutter Island (2010)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
In 1954, a U.S. marshal investigates the disappearance of a murderess who escaped from a hospital for the criminally insane. (138 mins.)
Director: Martin Scorsese
“ The darkest tale of love I have ever come across. An extremely disturbing psychological thriller touching upon the mysteries of human mind and heart. ” - CyanideDipped
 
2.
The Machinist (2004)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
An industrial worker who hasn't slept in a year begins to doubt his own sanity. (101 mins.)
Director: Brad Anderson
“ The bleak tale of guilt. Another psychological thriller detailing how the human mind's 'fail-safe' system works. What stands out in this movie is the brilliant imagery shown through expert cinematography which complements the bleakness inherent in the story. ” - CyanideDipped
 
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
“ A complex drama, detailing out the relationship of a young couple living in a Connecticut suburb during the mid-1950s. It is not love that matters, but what comes after it. And this movie is an excellent venture into the chasms of emptiness that are created by passion blinded by lust we wrongly dubbed as love once. "The hopeless emptiness? Now, you've said it. Plenty of people are on to the emptiness, but it takes real guts to see the hopelessness... " says it all. ” - CyanideDipped
 
4.
K-PAX (2001)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
PROT is a patient at a mental hospital who claims to be from a far away planet. His psychiatrist tries to help him, only to begin to doubt his own explanations. (120 mins.)
Director: Iain Softley
“ What a gem of a movie! An excellent example of how well psychological thrillers can be written and directed. ” - CyanideDipped
 
5.
Awakenings (1990)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
The victims of an encephalitis epidemic many years ago have been catatonic ever since, but now a new drug offers the prospect of reviving them. (121 mins.)
Director: Penny Marshall
“ This movie taught me a lesson or two in acting. Watch out for DeNiro! ” - CyanideDipped
 
6.
The Deer Hunter (1978)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
An in-depth examination of the ways in which the U.S. Vietnam War impacts and disrupts the lives of people in a small industrial town in Pennsylvania. (183 mins.)
Director: Michael Cimino
“ Excellently depressing! ” - CyanideDipped
 
7.
The Life of David Gale (2003)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A man against capital punishment is accused of murdering a fellow activist and is sent to death row. (130 mins.)
Director: Alan Parker
“ Darkest venture on capital punishment I have come across yet! ” - CyanideDipped
 
8.
Serpico (1973)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
The true story about an honest New York cop who blew the whistle on rampant corruption in the force only to have his comrades turn against him. (130 mins.)
Director: Sidney Lumet
“ What's depressing about this movie is the fact that Serpico never really did survive the wound! ” - CyanideDipped
 
9.
The Pledge (2001)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A retiring police chief pledges to catch the killer of a young child. (124 mins.)
Director: Sean Penn
“ Often neglected by usual movie-lovers, this is one of the bleakest tales of obsession that you'd ever lay your eyes on. Brilliant story-telling! ” - CyanideDipped
 
10.
Mystic River (2003)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
With a childhood tragedy that overshadowed their lives, three men are reunited by circumstance when one has a family tragedy. (138 mins.)
Director: Clint Eastwood
“ Disturbing tale of friendship, love and betrayal. Very well directed! ” - CyanideDipped
 
11.
You Don't Know Jack (2010 TV Movie)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A look at the life and work of doctor-assisted suicide advocate Jack Kevorkian. (134 mins.)
Director: Barry Levinson
“ Al Pacino at his best! What can be more depressing than suicide... now imagine the idea of aided suicide. There is a reason suicide clinics have never been so popular! ” - CyanideDipped
 
12.
Citizen Kane (1941)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
Following the death of a publishing tycoon, news reporters scramble to discover the meaning of his final utterance. (119 mins.)
Director: Orson Welles
“ An absolute classic. ” - CyanideDipped
 
13.
Antichrist (2009)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
A grieving couple retreat to their cabin in the woods, hoping to repair their broken hearts and troubled marriage. But nature takes its course and things go from bad to worse. (108 mins.)
Director: Lars von Trier
 
14.
The Insider (1999)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
A research chemist comes under personal and professional attack when he decides to appear in a "60 Minutes" expose on Big Tobacco. (157 mins.)
Director: Michael Mann
 
15.
Under Suspicion (2000)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A lawyer is asked to come to the police station to clear up a few loose ends in his witness report of a foul murder... (110 mins.)
Director: Stephen Hopkins
“ Ah... what can I say about this one... an absolute gem of a psychological drama! ” - CyanideDipped
 
16.
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
 
17.
Black Swan (2010)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A committed dancer wins the lead role in a production of Tchaikovsky's "Swan Lake" only to find herself struggling to maintain her sanity. (108 mins.)
 
18.
Pay It Forward (2000)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A young boy attempts to make the world a better place after his teacher gives him that chance. (123 mins.)
Director: Mimi Leder
 
19.
Oldboy (2003)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
After being kidnapped and imprisoned for fifteen years, Oh Dae-Su is released, only to find that he must find his captor in five days. (120 mins.)
Director: Chan-wook Park
 
20.
Collateral (2004)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A cab driver finds himself the hostage of an engaging contract killer as he makes his rounds from hit to hit during one night in Los Angeles. (120 mins.)
Director: Michael Mann
 
21.
Se7en (1995)
    1 2 3 4 5 6 7 8 9 10 8.6/10 X  
Two detectives, a rookie and a veteran, hunt a serial killer who uses the seven deadly sins as his modus operandi. (127 mins.)
Director: David Fincher
 
22.
Apocalypse Now (1979)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
During the Vietnam War, Captain Willard is sent on a dangerous mission into Cambodia to assassinate a renegade colonel who has set himself up as a god among a local tribe. (153 mins.)
Director: Francis Coppola
 
23.
Fallen (1998)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Homicide detective John Hobbes witnesses the execution of serial killer Edgar Reese. Soon after the execution the killings start again, and they are very similar to Reese's style. (124 mins.)
Director: Gregory Hoblit
 
24.
A Streetcar Named Desire (1951)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
Disturbed Blanche DuBois moves in with her sister in New Orleans and is tormented by her brutish brother-in-law while her reality crumbles around her. (122 mins.)
Director: Elia Kazan
“ Best, most intense Vivian Leigh for me! ” - CyanideDipped
 
25.
Blue Valentine (2010)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
The relationship of a contemporary married couple, charting their evolution over a span of years by cross-cutting between time periods. (112 mins.)
 
26.
Awake (2007)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
The story focuses on a man who suffers "anesthetic awareness" and finds himself awake and aware, but paralyzed, during heart surgery. His mother must wrestle with her own demons as a turn of events unfolds around them, while trying to unfold the story hidden behind her son's young wife. (84 mins.)
Director: Joby Harold
 
27.
The Godfather: Part III (1990)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
In the midst of trying to legitimize his business dealings in New York and Italy in 1979, aging Mafia don Michael Corleone seeks to avow for his sins while taking a young protégé under his wing. (162 mins.)
 
28.
Inception (2010)
    1 2 3 4 5 6 7 8 9 10 8.8/10 X  
A thief, who steals corporate secrets through use of dream-sharing technology, is given the inverse task of planting an idea into the mind of a CEO. (148 mins.)
 
29.
Memento (2000)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
A man juggles searching for his wife's murderer and keeping his short-term memory loss from being an obstacle. (113 mins.)
 
30.
Irreversible (2002)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Events over the course of one traumatic night in Paris unfold in reverse-chronological order as the beautiful Alex is brutally raped and beaten by a stranger in the underpass. (97 mins.)
Director: Gaspar Noé
 
31.
Proof (2005)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
The daughter of a brilliant but mentally disturbed mathematician, recently deceased, tries to come to grips with her possible inheritance: his insanity. Complicating matters are one of her father's ex-students, who wants to search through his papers, and her estranged sister, who shows up to help settle his affairs. (100 mins.)
Director: John Madden
 
32.
Dahmer (2002)
    1 2 3 4 5 6 7 8 9 10 5.6/10 X  
Biopic about notorious American serial killer Jeffrey Dahmer, taking place in both the past and the present. (101 mins.)
Director: David Jacobson
 
33.
Sinister (2012)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Washed-up true-crime writer Ellison Oswalt finds a box of super 8 home movies that suggest the murder he is currently researching is the work of a serial killer whose work dates back to the 1960s. (110 mins.)
 
34.
Cube (1997)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Six complete strangers of widely varying personality characteristics are involuntarily placed in an endless kafkaesque maze containing deadly traps. (90 mins.)
Director: Vincenzo Natali
 
35.
The Elephant Man (1980)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A Victorian surgeon rescues a heavily disfigured man who is mistreated while scraping a living as a side-show freak. Behind his monstrous facade, there is revealed a person of intelligence and sensitivity. (124 mins.)
Director: David Lynch
 
36.
The Human Stain (2003)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
When a disgraced former college dean has a romance with a mysterious younger woman haunted by her dark, twisted past, he is forced to confront a shocking fact about his own life that he has kept secret for 50 years. (106 mins.)
Director: Robert Benton
 
37.
Being Flynn (2012)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
Working in a Boston homeless shelter, Nick Flynn re-encounters his father, a con man and self-proclaimed poet. Sensing trouble in his own life, Nick wrestles with the notion of reaching out yet again to his dad. (102 mins.)
Director: Paul Weitz
 
38.
Ruby Sparks (2012)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A novelist struggling with writer's block finds romance in a most unusual way: by creating a female character he thinks will love him, then willing her into existence. (104 mins.)
 
39.
21 Grams (2003)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
A freak accident brings together a critically ill mathematician, a grieving mother, and a born-again ex-con. (124 mins.)
 
40.
May (2002)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A lonely young woman traumatized by a difficult childhood and her increasingly desperate attempts to connect with the people around her is sent into a murderous tailspin. (93 mins.)
Director: Lucky McKee
 
41.
We Need to Talk About Kevin (2011)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
Kevin's mother struggles to love her strange child, despite the increasingly vicious things he says and does as he grows up. But Kevin is just getting started, and his final act will be beyond anything anyone imagined. (112 mins.)
Director: Lynne Ramsay
 
42.
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.)
 
43.
Everybody's Fine (2009)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A widower who realized his only connection to his family was through his wife sets off on an impromptu road trip to reunite with each of his grown children. (99 mins.)
Director: Kirk Jones
 
44.
The Remains of the Day (1993)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
A butler who sacrificed body and soul to service in the years leading up to World War II realizes too late how misguided his loyalty was to his lordly employer. (134 mins.)
Director: James Ivory
 
45.
Othello (1981 TV Movie)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A general becomes convinced that his wife is having an affair, even though there is no evidence. (195 mins.)
Director: Jonathan Miller
 
46.
Half Nelson (2006)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
An inner-city junior high school teacher with a drug habit forms an unlikely friendship with one of his students after she discovers his secret. (106 mins.)
Director: Ryan Fleck
 
47.
One Flew Over the Cuckoo's Nest (1975)
    1 2 3 4 5 6 7 8 9 10 8.7/10 X  
A criminal pleads insanity after getting into trouble again and once in the mental institution rebels against the oppressive nurse and rallies up the scared patients. (133 mins.)
Director: Milos Forman
 
48.
A Serbian Film (2010)
    1 2 3 4 5 6 7 8 9 10 5.2/10 X  
An aging porn star agrees to participate in an "art film" in order to make a clean break from the business, only to discover that he has been drafted into making a pedophilia and necrophilia themed snuff film. (104 mins.)
 
49.
A Clockwork Orange (1971)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
In future Britain, Alex DeLarge, a charismatic and psycopath delinquent, who likes to practice crimes and ultra-violence with his gang, is jailed and volunteers for an experimental aversion therapy developed by the government in an effort to solve society's crime problem - but not all goes according to plan. (136 mins.)
Director: Stanley Kubrick
 
50.
The Flock (2007)
    1 2 3 4 5 6 7 8 9 10 5.7/10 X  
This film is about a hyper-vigilant employee of the department of public safety who, while training his young female replacement, has to track down a missing girl who he is convinced is connected to a paroled sex offender he is investigating. (105 mins.)
Director: Andrew Lau
 
51.
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
 
52.
Jack Goes Boating (2010)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
A limo driver's blind date sparks a tale of love, betrayal, friendship, and grace centered around two working-class New York City couples. (91 mins.)
 
53.
The Master (2012)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A Naval veteran arrives home from war unsettled and uncertain of his future - until he is tantalized by The Cause and its charismatic leader. (144 mins.)
 
54.
One Hour Photo (2002)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A mentally unstable photo developer begins to attack a middle-class family after his obsession with them becomes more sick and disturbing than any of them could imagine. (96 mins.)
Director: Mark Romanek
 
55.
The Place Beyond the Pines (2012)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A motorcycle stunt rider turns to robbing banks as a way to provide for his lover and their newborn child, a decision that puts him on a collision course with an ambitious rookie cop navigating a department ruled by a corrupt detective. (140 mins.)