The 20 most chilling true crime documentaries on HBO Max

Looking to get hooked on a new tale of true crime? HBO Max has you covered.

The streaming service boasts tons of great documentaries, many of them centered on criminal activity. But for the purposes of this list, we’ve limited the definition of the genre to focus exclusively on those all-consuming stories that drive you to marathon-viewing multiple, terrifying tales. You know, those whodunnits — or more often, those why’d-they-do-its — that plunge you into a rabbit hole of armchair psychology, amateur sleuthing, and nonfiction nightmares.

Here are the 19 most gripping true crime projects, both series and films, now on HBO Max.

20. The Lady and the Dale*

the 20 most chilling true crime documentaries on hbo max

The Lady and the Dale Credit: Courtesy of hbo

HBO has a library of sensational true crime offerings, yet this 2021 mini-series is uniquely fascinating. Directors Nick Cammilleri and Zackary Drucker unfurl the times and trials of Elizabeth Carmichael, who was not only a nationally recognized automobile executive and infamous con artist, but also a wife, mother, and transgender trailblazer.

For decades, her story has been framed by those who despise her, resulting in a narrative rife with speculation and transphobia. In this challenging and boldly funny four-episode documentary mini-series, Carmichael’s story is reclaimed by balancing the perspective of her haters with in-depth interviews with those who knew her best. With animated photography, a playful soundtrack, and a cheeky sense of adventure, The Lady and The Dale aims not only to showcase the complexity of the late Carmichael, but also to capture her spirit. All this makes for a watch that is surprising, thrilling, and unforgettable.

How to watch: The Lady and the Dale is streaming on HBO Max.

19. Class Action Park

When most people think “true crime,” their minds leap to bloody murders, twisted thinking, and criminal enterprises. They don’t generally think: water slides. But Class Action Park is a special case. This superb documentary from directors Seth Porges and Chris Charles Scott III is an equal mix of theme park nostalgia, hilariously dumb ideas, and — here’s where the crimes come in — the unfortunate victims of said dumb ideas. The movie tells the story of Action Park, an infamous New Jersey water park known for its dangerous attractions and lax approach to safety.

From the day it opened in 1978 until its closing in 1996, at least six people died and literally countless others were injured. Class Action Park tells the story of how that all happened while also laying out the circumstances that kept this memorably dangerous tourist attraction in business for almost two decades. — Adam Rosenberg, Senior Entertainment Reporter

How to watch: Class Action Park is now streaming on HBO Max.

18. Thought Crimes: The Case of the Cannibal Cop

the 20 most chilling true crime documentaries on hbo max

Best true crime documentaries on HBO Max Credit: hbo

Another project from director Erin Carr, Thought Crimes: The Case of the Cannibal Cop follows the strange case of former NYPD officer Gilberto Valle.

In 2012, Valle was arrested for conspiring to kidnap, rape, kill, and cannibalize women after his wife discovered hundreds of internet chat messages describing the acts in his search history. The apparent fetish seemed to go beyond hypothetical imagery, when Valle began improperly accessing the National Crime Information Center database through his NYPD credentials and drawing up comprehensive abduction plans for women he actually knew.

The documentary navigates the sticky legal area deftly, posing fascinating questions about what Valle’s case means for the future of crime in the digital age. — A.F.

How to watch: Thought Crimes: The Case of the Cannibal Cop is now streaming on HBO Max.

17. Mommy Dead and Dearest

Documentarian and true crime heavy hitter Erin Lee Carr — whose engrossing works appear twice more on this list — covers the bizarre murder of Dee Dee Blanchard in Mommy Dead and Dearest. The 2017 film tells the story of Gypsy Rose Blanchard, a 19-year-old victim of Munchausen syndrome by proxy, who after a lifetime of abuse conspired to murder her mother in 2015.

Some viewers will recognize the case from its serialized dramatization in Hulu’s The Act,but Carr’s telling offers a more nuanced look at the fact pattern. It’s a flummoxing conundrum of justice that sees mother and daughter trade places as victim and attacker, and raises serious questions about the criminal justice system’s ability to hand down levelheaded verdicts in morally complicated cases. — Alison Foreman, Entertainment Reporter

How to watch: Mommy Dead and Dearest is now streaming on HBO Max.

16. The Cheshire Murders

the 20 most chilling true crime documentaries on hbo max

Best true crime documentaries on HBO Max Credit: hbo max

Directed and produced by Kate Davis and David Heilbroner, The Cheshire Murders chronicles a horrific home invasion that devastated a small town in Connecticut.

In the early hours of July 23, 2007, two men entered a suburban residence and began a campaign of terror against a family of four that left only father Dr. William Petit alive. It’s a truly disturbing account, which includes graphic descriptions of child rape and torture.

This project is sometimes regarded as being staunchly in favor of the death penalty, featuring damning interviews with the attackers’ families actually recommending the two convicted men be sentenced to death. However, it also offers a disturbing look at the alarming lack of transparency from police regarding the perpetrators’ arrests and trials. — A.F.

How to watch: The Cheshire Murders is now streaming on HBO Max.

15. There’s Something Wrong with Aunt Diane

On July 26, 2009, Diane Schuler traveled 1.7 miles in the wrong direction on the Taconic State Parkway in upstate New York. When her minivan collided head-on with an SUV, she, her daughter, three of her nieces, and all of the passengers in the other vehicle died.

In director Liz Garbus’ There’s Something Wrong With Aunt Diane, Schuler’s family members, witnesses, and investigators attempt to make sense of the bizarre decisions Schuler made that day. Her blood alcohol content was reportedly .19% at the time of the collision, but Schuler had no history of alcoholism and had appeared sober to witnesses shortly beforehand.

Garbus prioritizes deep and complex analysis over a tidy narrative in her take on the case. It’s a sympathetic but truthful account that will leave you with plenty to chew over. — A.F.

How to watch: There’s Something Wrong with Aunt Diane is now streaming on HBO Max.

14. Beware the Slenderman

If you’re a regular true crime fan, chances are you already know everything there is to know about the so-called “Slenderman stabbing.” But uh, if you don’t? Buckle way, way up.

In this haunting documentary from director Irene Taylor Brodsky, we revisit the 2014 attempted murder of 12-year-old Payton Leutner. The attack was carried out by two other 12-year-old girls, Morgan Geyser and Anissa Weier, who told Wisconsin authorities they attacked their friend in an effort to impress the online character Slenderman. The film offers a chilling glimpse into the sometimes warped interactions between adolescent minds and the internet that’s imperfect to say the least, but a unique watch. Some of these interviews really stick with you. — A.F.

How to watch: Beware the Slenderman is now streaming on HBO Max.

13. The Case Against Adnan Syed

the 20 most chilling true crime documentaries on hbo max

The Case Against Adnan Syed Credit: Courtesy of hbo max

Directed by Academy Award nominee Amy Berg, The Case Against Adnan Syed can be understood and appreciated as a standalone project. But for most viewers, the four-part docuseries serves as a companion piece to the watershed Serial podcast, which brought the murder of Baltimore County high school student Hae Min Lee to international attention in 2014.

The series explores the media fervor brought on by the podcast’s popularity, as well as recounts the story from investigation through the 2016 post-conviction relief hearing of Adnan Syed, the man convicted of the murder. All told, the project isn’t likely to change your mind about the case, but it offers new insights and evidence worth your (and possibly the court’s) attention. — A.F.

How to watch:The Case Against Adnan Syed is now streaming on HBO Max.

12. Capturing the Friedmans

In this Academy Award-nominated crime documentary, director Andrew Jarecki looks at the collapse of a family when father Arnold and son Jesse are investigated and later tried for charges of child molestation. The result is a chilling juxtaposition of what predators can choose to present to the world and their true nature behind closed doors. — A.F. *

How to watch: Capturing the Friedmans is now streaming on HBO Max.

11. The Jinx: The Life and Deaths of Robert Durst

Efforts to put suspected serial killer Robert Durst behind bars have spanned decades. In The Jinx: The Life and Deaths of Robert Durst, filmmaker Andrew Jarecki recaps the chillingly charmed life of the New York real estate heir, who in 2021 is just now standing trial for the 2000 murder of Susan Berman. Berman is one of three victims tied to Durst; he is also accused of having killed his first wife Kathleen McCormack in 1982 and his neighbor Morris Black in 2001.

Against the advice of his attorneys, Durst actively participated in the creation of the 2014 docuseries. Across six episodes, Durst sits down with Jarecki for a series of disturbing interviews, a number of which have since been treated as evidence in the continued prosecution of Durst. As far as portraits of truly terrible people go, The Jinx remains one of the most horrific. — A.F.

How to watch: The Jinx: The Life and Deaths of Robert Durst is now streaming on HBO Max.

10. Yusuf Hawkins: Storm Over Brooklyn

the 20 most chilling true crime documentaries on hbo max

Yusuf Hawkins: Storm Over Brooklyn Credit: Courtesy of HBO

The murder of Yusuf Hawkins was a hate crime, no question. But in Yusuf Hawkins: Storm Over Brooklyn, director Muta’Ali entertains the other theories that were considered in the 1989 shooting death of the Black 16-year-old just enough for you to understand the power of the white narrative Hawkins’ family was up against when seeking justice.

Thoughtful and well-paced, the 2020 documentary goes beyond the tragic facts of this death to steadily reveal the surrounding culture of racism in New York City during the late ’80s and early ’90s that made so many like it possible. It’s a heartbreaking true crime entry, but a crucial one. — A.F.

How to watch: Yusuf Hawkins: Storm Over Brooklyn is now streaming on HBO Max.

9. Who Killed Garrett Phillips?

The 2011 death of Garrett Phillips spurred a multitude of tragedies. Not only did a New York family lose their 12-year-old son in a senseless act of violence, but the subsequent investigation left a Black man suffering greatly under a legal system ravaged by racial bias.

Another true crime film from director Liz Garbus (There’s Something Wrong With Aunt Diane), Who Killed Garrett Phillips? relentlessly seeks justice on both fronts. Asking the right questions at the just the right times, Garbus produces a compelling narrative that is at once an indictment of police failings and a rallying cry for identifying the real killer. — A.F.

How to watch: Who Killed Garrett Phillips? is now streaming on HBO Max.

8. Atlanta’s Missing and Murdered: The Lost Children

Director Sam Pollard tackles one of the most troubling crime trends in American history in Atlanta’s Missing and Murdered: The Lost Children. Between 1979 and 1981, at least 30 Black children were abducted and murdered. But prosecutors’ decision to assign all of those deaths to the convicted serial killer Wayne Williams disturbed many who doubted his involvement every case.

Over five episodes, Pollard tracks the story from the beginning of the killings to the reopening of the investigation in 2019. It’s a comprehensive look at the insidious racism that has plagued Atlanta policing for decades, that only grows in importance. The tragedy of these cases, however, is that the decision to prematurely close them in the ’80s may mean they’re unsolvable now. — A.F.

How to watch: Atlanta’s Missing and Murdered: The Lost Children is now streaming on HBO Max.

7. I Love You, Now Die

the 20 most chilling true crime documentaries on hbo max

I Love You, Now Die Credit: Courtesy of HBO

Another true crime project from Erin Carr, I Love You, Now Die: The Commonwealth vs. Michelle Carter is a two-part look at one of the most senseless crimes of the modern age. On July 13, 2014, 18-year-old Conrad Roy died by suicide in a Kmart parking lot in Massachusetts. His girlfriend, 19-year-old Michelle Carter, not only knew of her boyfriend’s plan to die by carbon monoxide poisoning, but actively encouraged him to go through with it in a series of bewildering text messages that would later land her in court on charges of involuntary manslaughter.

The series follows Carter’s efforts to prove her innocence, posing fascinating questions about what crimes can be committed online. This one is tough viewing, both for its heart-wrenching depiction of Roy’s mental health crisis and for the helplessness one feels in knowing Roy could have been saved if Carter had interceded. — A.F.

How to watch: I Love You, Now Die is now streaming on HBO Max.

6. The Inventor: Out for Blood in Silicon Valley

Enter the absolutely unreal delusion of disgraced Theranos founder Elizabeth Holmes in The Inventor: Out for Blood in Silicon Valley. Academy Award winner Alex Gibney walks viewers through the (alleged) scam concocted by the ex-CEO, which not only garnered the support of numerous high-profile investors but even saw its entirely fake technology — a blood-testing device called “Edison” — begin a pseudo rollout in actual pharmacies.

Repurposing some incredible footage of Holmes intended for use in a Theranos advertising campaign, Gibney renders a stunning portrait of a (again, alleged) con artist. The result is a mesmerizing watch that will make you question how easy you’d be to fool when faced with one of the most notorious liars of the 21st century. — A.F.

How to watch: The Inventor: Out for Blood in Silicon Valley is now streaming on HBO Max.

5. Murder on Middle Beach

It should go without saying, but true crime is a better genre when victims and survivors lead the way. Murder on Middle Beach champions just this idea, as debut filmmaker Madison Hamburg investigates and reflects on the unsolved murder of his mother Barbara Hamburg in 2010.

A four-part story shot over eight years, the docuseries chronicles Hamburg’s journey to understand who killed his mom and why. What begins as a look into his family’s most fraught relationships soon takes Madison into a hidden world of scams and hierarchy of which he didn’t know his mother was a part. It’s a fascinating, if slightly unsatisfying, project you’ll want to binge for its winding narrative style and surprising last-act revelations. — A.F.

How to watch: Murder on Middle Beach is now streaming on HBO Max.

4. Paradise Lost: The Child Murders at Robin Hood Hills

the 20 most chilling true crime documentaries on hbo max

Credit: hbo

This 1996 documentary from HBO was the first of many to question the verdict reached in the infamous case of Arkansas’ West Memphis Three. And while there’s plenty you’ll want to research about the case after seeing the movie — seriously, you’ve got 25 years of legal developments that aren’t accounted for here — it remains one of the most well-regarded perspectives on the disturbing crime available, not to mention an utterly transfixing viewing experience.

On May 5, 1993, three 8-year-old boys were found dead and mutilated in a wooded area known as Robin Hood Hills. Local teenagers Damien Echols, Jessie Misskelley Jr., and Jason Baldwin were soon identified as prime suspects in the crime, but their connections to the murders were flimsy. Directors Joe Berlinger and Bruce Sinofsky’s Paradise Lost is an essential true crime watch that always strikes a nerve. — A.F.

How to watch: Paradise Lost: The Child Murders at Robin Hood Hills is now streaming on HBO Max.

3. Behind Closed Doors

The double homicide of 13-year-old Aarushi Talwar and her family’s servant 45-year-old Hemraj Banjade remains a world-shaking event for the people of Noida, India.

In Behind Closed Doors, documentarian P.A. Carter takes viewers into the heart of the media storm that erupted when the two were found dead in 2008. Over two parts, Carter interviews those closest to the case about everything from the small details needed to nab the killer to the broader societal issues that made this particular investigation so tumultuous. It’s a particularly intriguing true crime entry, considering it allows for a broader discussion of how justice is or isn’t carried out internationally in a genre typically dominated by western audiences. — A.F.

How to watch: Behind Closed Doors is now streaming on HBO Max.

2. I’ll Be Gone in the Dark

One of the best portraits of a true crime writer to date, director Liz Garbus’ I’ll Be Gone in the Dark serves as both a look into the terrifying Golden State Killer (also known as the “Original Night Stalker” and “East Area Rapist”) and the woman who would stop at nothing to identify him.

Michelle McNamara, who died suddenly in 2016, dedicated years of her life to finding the man responsible for a string of murders, rapes, and burglaries across California between 1973 and 1986, despite not knowing anyone directly impacted by his crimes. A book chronicling her work, also titled I’ll Be Gone in the Dark, was released posthumously and the docuseries serves as a sort of companion piece — filled with loving remembrances and overwhelming admiration for McNamara.

As far as true crime “fans” go, McNamara was the best of us. Her unrelenting passion for justice leaps from the page and screen even now, and will serve as an inspiration always. — A.F.

How to watch: I’ll Be Gone in the Dark is now streaming on HBO Max.

1. McMillions

the 20 most chilling true crime documentaries on hbo max

McMillions Credit: Courtesy of HBO

For more than a decade starting in 1989, a veritable army of crooks and stooges bilked McDonald’s out of $24 million worth of winnings from its annual McDonald’s Monopoly sweepstakes. It was such a sprawling scheme that HBO turned it into a documentary miniseries directed by James Lee Hernandez and Brian Lazarte. Across six episodes, the fascinating and frequently hilarious doc introduces us to colorful characters on both sides of the law as it digs into the particulars of the criminal enterprise and how it eventually fell apart.

By the time it’s all over, you’ll know the who, what, when, where, why, and how of the historic McDonald’s Monopoly fraud case. But you’ll also be left with plenty of questions about what McMillions’ most memorable character, FBI Agent Doug Matthews, isn’t telling us. — A.R.

How to watch: McMillions is now streaming on HBO Max.

Asterisks (*) indicate the entry description comes from a previous Mashable streaming list.

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