The Most Challenging Films You Will Ever See

Movies where your stance as an audience member will be tried, worked over and more often than not tired out. Whether it be because of prolonged silence, excessive length, confusing plots that enrage the brain or good old fashioned graphic violence and sex, these movies will surely test you to the limits of your squeamishness... either that or your attention span.

No particular order.
View:
Log in to copy items to your own lists.
1.
Paint Drying (2016 Documentary)
    1 2 3 4 5 6 7 8 9 10 9.4/10 X  
10 hours of paint drying on a wall. (607 mins.)
Director: Charlie Lyne
 
2.
Aaaaaaaah! (2015)
    1 2 3 4 5 6 7 8 9 10 4.6/10 X  
Ever imagined what life would be like if humans were apes in modern life? That is the portrayal in this deeply thought provoking mind boggle. (79 mins.)
Director: Steve Oram
 
3.
Shoah (1985 Documentary)
    1 2 3 4 5 6 7 8 9 10 8.4/10 X  
Claude Lanzmann's epic documentary recounts the story of the Holocaust through interviews with witnesses - perpetrators as well as survivors. (566 mins.)
Director: Claude Lanzmann
 
4.
Happiness (1998)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
The lives of several individuals intertwine as they go about their lives in their own unique ways, engaging in acts society as a whole might find disturbing in a desperate search for human connection. (134 mins.)
Director: Todd Solondz
 
5.
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
 
6.
The Garden (2017)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
After a silent, masked individual encounters a man with a television for an arm; horror, euphoria and madness ensue. (55 mins.)
Director: Finn Callan
 
7.
Salò, or the 120 Days of Sodom (1975)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
In World War II Italy, our fascist libertines round up nine adolescent boys and girls and subject them to one hundred and twenty days of physical, mental and sexual torture. (117 mins.)
 
8.
The Room (2003)
    1 2 3 4 5 6 7 8 9 10 3.6/10 X  
Johnny is a successful banker who lives happily in a San Francisco townhouse with his fiancée, Lisa. One day, inexplicably, she gets bored with him and decides to seduce his best friend, Mark. From there, nothing will be the same again. (99 mins.)
Director: Tommy Wiseau
 
9.
Inland Empire (2006)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
As an actress starts to adopt the persona of her character in a film, her world starts to become nightmarish and surreal. (180 mins.)
Director: David Lynch
 
10.
The Tree of Wooden Clogs (1978)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
The life inside a farm in Italy at the beginning of the century. Many poor country families live there... (186 mins.)
Director: Ermanno Olmi
 
11.
Jeanne Dielman, 23 Commerce Quay, 1080 Brussels (1975)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A lonely widowed housewife does her daily chores, takes care of her apartment where she lives with her teenage son, and turns the occasional trick to make ends meet. However, something happens that changes her safe routine. (201 mins.)
 
12.
Elephant (2003)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Several ordinary high school students go through their daily routine as two others prepare for something more malevolent. (81 mins.)
Director: Gus Van Sant
 
13.
The Mirror (1975)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A dying man in his forties remembers his past. His childhood, his mother, the war, personal moments and things that tell of the recent history of all the Russian nation. (107 mins.)
 
14.
Pink Flamingos (1972)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
Notorious Baltimore criminal and underground figure Divine goes up against a sleazy married couple who make a passionate attempt to humiliate her and seize her tabloid-given title as "The Filthiest Person Alive". (93 mins.)
Director: John Waters
 
15.
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
 
16.
Cannibal Holocaust (1980)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
During a rescue mission into the Amazon rainforest, a professor stumbles across lost film shot by a missing documentary crew. (95 mins.)
Director: Ruggero Deodato
 
17.
Uncle Boonmee Who Can Recall His Past Lives (2010)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
Dying of kidney disease, a man spends his last, somber days with family, including the ghost of his wife and a forest spirit who used to be his son, on a rural northern Thailand farm. (114 mins.)
 
18.
Earthlings (2005 Documentary)
    1 2 3 4 5 6 7 8 9 10 8.7/10 X  
Using hidden cameras and never-before-seen footage, Earthlings chronicles the day-to-day practices of the largest industries in the world, all of which rely entirely on animals for profit. (95 mins.)
Director: Shaun Monson
 
19.
Song to Song (2017)
    1 2 3 4 5 6 7 8 9 10 5.8/10 X  
Two intersecting love triangles. Obsession and betrayal set against the music scene in Austin, Texas. (129 mins.)
Director: Terrence Malick
 
20.
The Cook, the Thief, His Wife & Her Lover (1989)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
The wife of an abusive criminal finds solace in the arms of a kind regular guest in her husband's restaurant. (124 mins.)
Director: Peter Greenaway
 
21.
2001: A Space Odyssey (1968)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
Humanity finds a mysterious, obviously artificial object buried beneath the Lunar surface and, with the intelligent computer H.A.L. 9000, sets off on a quest. (149 mins.)
Director: Stanley Kubrick
 
22.
Raw (2016)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
When a young vegetarian undergoes a carnivorous hazing ritual at vet school, an unbidden taste for meat begins to grow in her. (99 mins.)
Director: Julia Ducournau
 
23.
Only God Forgives (2013)
    1 2 3 4 5 6 7 8 9 10 5.7/10 X  
Julian, a drug-smuggler thriving in Bangkok's criminal underworld, sees his life get even more complicated when his mother compels him to find and kill whoever is responsible for his brother's recent death. (90 mins.)
 
24.
Ichi the Killer (2001)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
As sadomasochistic yakuza enforcer Kakihara searches for his missing boss he comes across Ichi, a repressed and psychotic killer who may be able to inflict levels of pain that Kakihara has only dreamed of. (129 mins.)
Director: Takashi Miike
 
25.
Martyrs (2008)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A young woman's quest for revenge against the people who kidnapped and tormented her as a child leads her and a friend, who is also a victim of child abuse, on a terrifying journey into a living hell of depravity. (99 mins.)
Director: Pascal Laugier
 
26.
Funny Games (2007)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Two psychopathic young men take a family hostage in their cabin. (111 mins.)
Director: Michael Haneke
 
27.
A Clockwork Orange (1971)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
In the future, a sadistic gang leader is imprisoned and volunteers for a conduct-aversion experiment, but it doesn't go as planned. (136 mins.)
Director: Stanley Kubrick
 
28.
Man Bites Dog (1992)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
A film crew follows a ruthless thief and heartless killer as he goes about his daily routine. But complications set in when the film crew lose their objectivity and begin lending a hand. (95 mins.)
 
29.
I Stand Alone (1998)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
A horse meat butcher's life and mind begins to breakdown as he lashes out against various factions of society while attempting to reconnect with his estranged daughter. (93 mins.)
Director: Gaspar Noé
 
30.
The Last House on the Left (1972)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
Two teenage girls head to a rock concert for one's birthday. While trying to score marijuana in the city, they are kidnapped and brutalized by a gang of psychotic convicts. (84 mins.)
Director: Wes Craven
 
31.
Titicut Follies (1967 Documentary)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
Documentary filmmaker Frederick Wiseman takes us inside the Massachusetts Correctional Institution Bridgewater where people stay trapped in their madness. (84 mins.)
 
32.
The Texas Chain Saw Massacre (1974)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
Two siblings visit their grandfather's grave in Texas along with three of their friends and are attacked by a family of cannibalistic psychopaths. (83 mins.)
Director: Tobe Hooper
 
33.
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.)
 
34.
Last Tango in Paris (1972)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
A young Parisian woman meets a middle-aged American businessman who demands their clandestine relationship be based only on sex. (129 mins.)
 
35.
Breathless (1960)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
A small-time thief steals a car and impulsively murders a motorcycle policeman. Wanted by the authorities, he reunites with a hip American journalism student and attempts to persuade her to run away with him to Italy. (90 mins.)
Director: Jean-Luc Godard
 
36.
Under the Skin (2013)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
A mysterious young woman seduces lonely men in the evening hours in Scotland. However, events lead her to begin a process of self-discovery. (108 mins.)
Director: Jonathan Glazer
 
37.
The Tree of Life (2011)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
The story of a family in Waco, Texas in 1956. The eldest son witnesses the loss of innocence and struggles with his parents' conflicting teachings. (139 mins.)
Director: Terrence Malick
 
38.
 
39.
Eraserhead (1977)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Henry Spencer tries to survive his industrial environment, his angry girlfriend, and the unbearable screams of his newly born mutant child. (89 mins.)
Director: David Lynch