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Life being stranger than fiction is such a self-evident truth, you may be sitting next to true crime documentaries waiting to happen and never know. The mother you saw driving off from the gas station with a car full of kids could cause a fatal crash minutes later; your boss could be defrauding the U.S. government; the church you’re a member of may secretly be a cult. Dark, we know. But over the last decade, HBO’s award-winning slate of true crime documentaries has done what true crime docs are meant to do when done well: dig into real life and complicate the world around the viewer.
Thanks to HBO, the world knows more about a cross-dressing millionaire serial killer, a mob affiliate who defrauded a McDonald’s promotional game for tens of millions of dollars, and enough stories about racist law enforcement to make you question the very people meant to protect you. While typically horrific, true crime docs are deeply engrossing survival training, often presented as cautionary tales meant to keep you hooked so you don’t go out into the world ignorant of the cleverly disguised pitfalls disguised as normalcy. They help sharpen the mind and are absolutely addicting to watch.
HBO Max has an extensive (and pretty impressive) library of HBO’s best true crime docs. Global Grind went through them all to unearth the most shocking and darkest ones for our top 10 roundup. These will surely leave you looking at life a little differently than before you pressed play.
10. I Love You, Now Die: The Commonwealth v. Michelle Carter
Can you kill someone with text messages? That’s one of the questions at the heart of the two-part docuseries I Love You, Now Die: The Commonwealth v. Michelle Carter which delves into 17-year-old Michelle Carter’s involvement in her 18-year-old Conrad Roy’s suicide in July 2014. The doc shows the disturbing text message exchange between the two prior to Roy’s death where Carter appears to encourage her boyfriend to take his life though he’s reluctant to do so.
Beyond those text messages, the doc explores the intricacy of the pair’s courtship, mental illness, and how technology is forcing the justice system to rethink culpability. In this hyper-connected world where people have taken their lives, you should watch this doc if you’ve ever wanted to know how the phone in your hand can cause harm to yourself and others.
9. The Mystery Of DB Cooper
On November 24, 1971, D.B. Cooper parachuted out of Boeing 757 airplane with $200,000 of ransom money he procured after threatening a flight crew with detonating a bomb. It is still the only unsolved airplane hijacking in the history of the United States of America. The Mystery of D.B. Cooper continues the investigative look into one of the greatest criminal mysteries in U.S. history with candid interviews with disparate strangers claiming to have a connection to Cooper, reenactments of the fateful night, and chats with the flight attendants and pilots on the plane that night. You’ll want to watch simply for the twists that include a story of the first woman to get a sex change in Washington State revealing to friends she used to be D.B. Cooper.
For years, Mcdonald’s held a promotion where anyone could win upwards of $1 million by simply collecting the right Monopoly tickets that came with their meal. Thanks to a conspiratorial network controlled by Jerry Jacobson, the head of security at the marketing agency behind the promotion, there were almost no legitimate $1 million winners between 1989-2001. For six shocking episodes, McMillions takes viewers through Jacobson’s insidious web of deception and criminality that includes the mob, blackmailed family members, and a fatal car accident.
You hear from the law enforcement agents who went to almost comically intricate lengths to catch Jacobson including disguising themselves as a TV production crew in order to stage a fake interview with a prize winner and get incriminating details on the illegal operation. If you’ve ever felt the American dream took too long to come to fruition, this doc will show the dark side of how people can prey on good people’s desire to get ahead.
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7. Who Killed Garret Phillips?
Who Killed Garret Phillips? is an eye-opening documentary delving into how the unfortunate death of 12-year-old Garret Phillps turned a predominantly white Potsdam community against Oral “Nick” Hillary, a Black man who was the ex-boyfriend of Garret’s mother. The two-part doc documents the five years following the murder and Hillary’s trial for murder while suspensefully weaving together caveats that make the fight for justice not so black and white.
No DNA tied Phillips to the crime scene and Potsdam’s sheriff’s deputy John Jones being seen on tape by Phillips before the murder was never explored by the police. Those are just a few of the wrinkles in the case explored by the doc that turns it into a frustrating look into a man whose freedom is jeopardized because of the color of his skin. Who Killed Garret Phillips? Is essential viewing for anyone who’s been harmed by a miscarriage of justice.
6. Three Days of Terror: The Charlie Hebdo Attacks
For three nightmarish days in January 2015, Paris, France witnessed multiple terrorist attacks perpetrated by two members of the extremist al-Qaeda on the Arabian Peninsula over satirical newspaper Charlie Hebdo’s critical caricature of the prophet Muhammed. Three Days of Terror: The Charlie Hebdo Attacks explores how France and the world at large responded to brothers Saïd and Chérif Kouachi’s vile attacks which left 12 people at Charlie Hebdo’s offices dead and inspired another extremist to hold 19 people hostage in a kosher supermarket resulting in five people dying, including the hostage-taker.
Three Days of Terror: The Charlie Hebdo Attacks puts you terrifyingly close to the carnage through tearful recollections of survivors and amateur videos shot from the people on the ground during the mayhem. But, it’s also a great choice for people interested in being inspired by how the world came together to denounce evil in solidarity.
5. There’s Something Wrong With Aunt Diane
On July 26, 2009, Diane Schuler was leaving her upstate New York vacation with her two children and three nieces before she began driving the opposite way on Taconic State Parkway causing a fatal crash resulting in the death of seven people including herself. Toxicology reports stated she had high levels of cannabis and alcohol in her system, so the crash was blamed on her driving inebriated. Here’s the twist that makes There’s Something Wrong With Aunt Diane: that toxicology is in direct contrast to the Diane her husband and sister-in-law knew.
In this 100-minute documentary, eyewitness accounts, family testimonials, previously unearthed medical records, and surveillance footage, and past trauma are used to not only meticulously breakdown the events that led to the crash, but also dissect the image of a woman who prided herself on perfection. Anyone who has ever publicly hidden their pain to chase perfection won’t be able to look away from this doc for a single second.
4. The Inventor: Out for Blood in Silicon Valley
The Inventor: Out for Blood in Silicon Valley is an artful look into how insanity and visions of the future are often indistinguishable when the former is means to make the world believe the latter. The exhaustively investigative doc looks into Elizabeth Holmes, a woman who promised to make her company Theranos the Apple of medicine by creating portable and at-home devices that can run hundreds of blood diagnostic tests without the need for syringes or doctor visits.
She became the youngest female self-made billionaire in 2014 and by 2017 she was being investigated by the Securities and Exchange Commission for lying about all of it. You hear from former employees who say the devices never worked and how Holmes played into the media and investors’ blind fascination with the appearance of genius to manipulate them into considering her the next Steve Jobs and giving her hundreds of millions of dollars for little more than a dream.
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3. Atlanta’s Missing And Murdered: The Lost Children
American history always proves Black people are perpetually hunted, and between 1979-1981, no Black child in Atlanta was safe from capture. For five hour-long episodes, the HBO docuseries Atlanta’s Missing And Murdered: The Lost Children revisits the two-year abduction and murder spree that left 30 African-American children and young adults either missing or dead and the rush for justice that may have buried the actual truth.
Through never-before-seen material, the documentary actually delivers new evidence that could connect this tragic time in Atlanta’s history to racial tensions that almost tore the city apart. With Atlanta Mayor Keisha Lance Bottoms reopening the investigation four decades later, Atlanta’s Missing And Murdered: The Lost Children is the perfect way to see how far we’ve come as a country and how much of America’s racist sins still need to be atoned for.
2. I’ll Be Gone In The Dark
Investigative journalist and author Michelle McNamara coined the “Golden State Killer” name for Joseph James DeAngelo Jr., the man responsible for at least 50 home-invasion rapes and a dozen murders across California in the 1970s and 1980s. I’ll Be Gone In The Dark, a six-part HBO docuseries named after her posthumously released book based on her tireless search to find the Golden State Killer, weaves together heart-crushing recounts of the killer’s rape survivors, never-before-seen home video footage of McNamara obsessing over finding the killer, and chilling excerpts from her book that often congeal years of evidence into uncomfortably vivid depictions of the Golden State Killer’s reign of terror.
You may come into the documentary trying to piece together the puzzle, but you’ll be drawn in by how the docuseries uses one woman’s fatal descent into trying uncover the truth as a reflection of us all. We see how McNamara inundating herself with horrific details and images every day could’ve contributed to her unexpected death in 2016, a look into how our own fixation on true crime might be detrimental to our lives.
1. The Jinx: The Life and Deaths of Robert Durst
Reclusive millionaire Robert Durst had been connected to the death of three people, including his ex-wife, across four decades until the Emmy Award-winning doc The Jinx: The Life and Deaths of Robert Durst came along. There’s no shortage of attention-grabbing material as it examines Durst’s suspiciously eccentric behavior over the years including cross-dressing as a deaf, mute woman to evade arrest.
The docuseries was so convincingly good, Durst was arrested for first-degree murder the day before the airing of the series finale by the Los Angeles Police Department which opened an invesgation into Durst based on new evidence shown in The Jinx. If you want to see how a true crime doc can help get justice through meticulous reporting, few are better watches than The Jinx: The Life and Deaths of Robert Durst.
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