The Top 5 Most Disturbing Documentaries Streaming On HBO Max

HBO Max has become something of a hub for true crime enthusiasts. The streamer has begun to rival Netflix as the most prolific purveyor of true crime content. HBO’s streaming arm has a varied selection of documentaries and docu-series chronicling a number of fascinating cases. So, with that in mind, we have put together a streaming guide that shines the spotlight on five noteworthy offerings you can watch right now. That’s right, armchair detectives, we’ve got five compelling recommendations for you to choose from. You truly can’t go wrong with any of the intriguing offerings showcased below!

The Cheshire Murders

The Cheshire Murders profiles the tragic home invasion and arson perpetrated by Linda Hayes (who was assigned male at birth and went by Steven Hayes at the time of the murders) and Joshua Komisarjevsky. The duo broke into a Cheshire, Connecticut home and murdered Jennifer Hawke-Petit and her daughters Hayley Petit and Michaela Petit. The perpetrators sexually assaulted two family members and burned their home to the ground to cover their tracks. The only family member to make it out of the ordeal alive was Dr. William Petit. 

The true crime case at the heart of this 2013 HBO documentary is profoundly tragic. The senseless loss of three lives is heartbreaking. And the suggestion that all three deaths might have been prevented if the police had intervened sooner is sickening. The aftermath of the tragedy is also rather disconcerting. Through audio footage of the interrogations, we get a harrowing view of the perpetrators’ lack of regard for human life. And it’s stomach-churning. The idea that anyone could commit such heinous acts and lack the empathy to understand the impact of their actions adds insult to injury. Nonetheless, The Cheshire Murders is a well-done documentary that provides some fascinating insight into the darkest corners of the human condition.    

Beware the Slenderman 

Beware the Slenderman chronicles the 2014 attempted murder of Payton “Bella” Leutner by Morgan Geyser and Anissa Weier. Geyser and Weier lured Leutner into the woods and stabbed her 19 times, narrowly missing a major artery. The young women believed they were committing the act of violence to appease the fictional character, Slenderman. Both of the perpetrators were severely detached from reality and wholeheartedly believed the Creepypasta character to be very real. 

The attempted murder profiled in this HBO documentary is horrifying. Almost as horrifying as the inciting act of violence is the notion that 12-year-old children are capable of such a brutal and senseless act. When I was in sixth grade, my life revolved around what the cafeteria was serving for lunch and whether recess was indoors or outdoors on any given day. So, to think that two children were busy planning to murder a classmate at the tender age of 12 is nothing short of mind-boggling. 

There’s Something Wrong with Aunt Diane 

This true crime doc depicts the fateful events leading up to the Taconic State Parkway crash in 2009, which saw Diane Schuler driving the wrong way down a stretch of freeway with a van full of children. She crashed into oncoming traffic and eight lives were lost. Her autopsy showed high levels of both alcohol and THC in her blood. The accident devastated her family and may have caused them to lose a certain amount of perspective. Throughout the film, they remain convinced that Diane must have unknowingly consumed the intoxicants. But that insistence is of little comfort to those impacted by her actions. 

There’s Something Wrong with Aunt Diane is an excruciating experience. The tragic details surrounding the Taconic State Parkway crash in 2009 are simply horrifying. And the idea that the entire ordeal could have been prevented if Diane Schuler had gotten help with the mental and physical pain she was experiencing makes the proceedings all the more excruciating to endure. There are numerous unanswered questions regarding how Diane ended up behind the wheel that day. That makes for a perplexing viewing experience as we watch the filmmakers search for answers and see Diane’s family double down on their disbelief and refuse to consider the implications of the facts with which they are presented. 

Who Killed Garrett Phillips?

Who Killed Garrett Phillips follows the investigation into Oral “Nick” Hillary in relation to the murder of 12-year-old Garrett Phillips. The boy was murdered in his room at an apartment complex where he lived with his mother. Investigators believe his killer escaped out the boy’s bedroom window after committing the crime. Though there is a number of other potential suspects, Hillary was the only one that received any substantial scrutiny, in spite of the very real possibility that he had nothing to do with Garrett’s murder. 

This HBO true crime docu-series is infuriating for very different reasons than many of its counterparts. Here, we have a case of what looks a lot like investigative tunnel vision. The detectives working on Garrett Phillips’ murder quickly zeroed in on a suspect with nearly no corroborating evidence. The inspectors came to believe that Oral “Nick” Hillary (the ex-boyfriend of Garret’s mother) was to blame for the crime. But from the outside looking in, it appears that Henry’s only crime may have been being one of the few Black men in the very white community of Potsdam, New York. Both the police and the prosecutor’s office zeroed in on Henry and blatantly refused to consider other potential suspects.

Capturing the Friedmans

The HBO documentary Capturing the Friedmans looks back on the investigation into Arnold and Jesse Friedman that began in 1984. The father and son ran a computer class out of their home in Great Neck, New York. When authorities discovered that the elder Friedman possessed child pornography, they began a full-fledged investigation. They eventually arrived at the conclusion that Arnold and Jesse Friedman were sexually abusing children in their computer classes. The problem is that the investigation seems to have been informed by a presumption of guilt, rather than fact-finding efforts

This may very well be the most disturbing true crime documentary I have endured. And I watch a lot of true crime programming. Not only is the subject matter surrounding the case quite triggering, but there is also the very real possibility that both Arnold and Jesse Friedman were innocent of the majority of the charges brought against them. In fact, it is quite possible that Jesse, Arnold’s son was innocent of any wrongdoing. Arnold, the patriarch of the Friedman clan openly admitted to possessing child pornography. But he vehemently denies the charges of abuse and sexual assault that were filed against him and his son. This may be another case of tunnel vision, albeit for very different reasons.

The documentary spotlights the total lack of physical evidence in the case, as well as the fact that many of the students believed to have been abused, refuted that any abuse ever transpired. 

Tags: Beware the Slenderman Capturing the Friedmans Dark Documentaries HBO Max The Cheshire Murders There’s Something Wrong with Aunt Diane True Crime Who Killed Garrett Phillips


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