Most Similar Movies to Henry: Portrait of a Serial Killer (1986)
If you are looking for movies like Henry: Portrait of a Serial Killer (1986), you might like movies tagged with keyword : thriller, crime, horror, psychological thriller, serial killer, violence, based on true events, dark, realism, indie film, low budget, chicago, documentary style, disturbing, moral ambiguity, anti-hero, social commentary, gritty, raw, controversial .
Henry: Portrait of a Serial Killer (1986), Surveillance (2008), Rampage (2009), The Golden Glove (2019), Hounds of Love (2016), Man Bites Dog (1992), The Honeymoon Killers (1969) ... Let's take a look at the following list...

Henry: Portrait of a Serial Killer (1986)
Ex-convict Henry (Michael Rooker) gets close to the sister (Tracy Arnold) of the prison buddy (Tom Towles) he teaches how to serial kill.
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Surveillance (2008)
Two FBI agents attempt to clarify the murders occurring in a desolate region. They approach the witnesses of the latest incident with the help of the local police. All of them hide something and all have wildly different stories to tell.
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Rampage (2009)
A man with a thirst for revenge builds a full body armor from Kevlar and goes on a killing spree.
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The Golden Glove (2019)
A serial killer strikes fear in the hearts of residents in 1970s Hamburg.
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Hounds of Love (2016)
Vicki Maloney is randomly abducted from a suburban street by a disturbed couple. As she observes the dynamic between her captors she quickly realises she must drive a wedge between them if she is to survive.
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Man Bites Dog (1992)
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.
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The Honeymoon Killers (1969)
An obese, embittered nurse doesn't mind if her toupee-wearing boyfriend romances and fleeces other women, as long as he takes her along on his con jobs.
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The Snowtown Murders (2011)
Based on true events, 16 year-old Jamie falls in with his mother's new boyfriend and his crowd of self-appointed neighborhood watchmen, a relationship that leads to a spree of torture and murder.
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Extremely Wicked, Shockingly Evil and Vile (2019)
A chronicle of the crimes of Ted Bundy from the perspective of Liz, his longtime girlfriend, who refused to believe the truth about him for years.
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Hobo with a Shotgun (2011)
A homeless vigilante blows away crooked cops, pedophile Santas, and other scumbags with his trusty pump-action shotgun.
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Cuck (2019)
When a frustrated loner gains popularity as an Alt-Right vlogger, the online echo chamber turns his fears into a deadly rage.
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Vengeance Is Mine (1979)
Chronological exploits of Iwao Enokizu, a murderous thief on the run.
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Psycho Raman (2016)
Ramanna, a maniac murderer, finds a soulmate in Raghavan, a policeman, who inspects his murder cases. He tries to make Raghavan realize how they both are similar.
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Department Q: A Conspiracy of Faith (2016)
Two intertwined cases linking the past with the present will require the aid of Department Q to catch an elusive serial killer, while time is running out.
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Tightrope (1984)
New Orleans single dad and cop Wes Block (Clint Eastwood) goes after a serial rapist-killer, but when he gets too close to the target, the hunter suddenly becomes the hunted.
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Cure (1997)
A Tokyo detective (Koji Yakusho) investigates a series of murders committed in exactly the same way by people who seem to have no connection.
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Red Riding: 1983 (2009)
The disappearance of a young girl leads a Yorkshire detective (David Morrissey) to believe that he may have helped convict the wrong man of murder three years earlier.
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