The human condition is a fractured, fluid, and everchanging condition. No two beings are entirely alike, and some are genuinely evil. The world has long been fascinated with dark and depraved nature(s) of the human condition, and this interest is no more evident than in the recent boom of true crime storytelling — from podcasts to documentaries. And one of the most interesting subsets of true crime is that of the serial killer, the lone being fueled by murderous intent. Serial killers have existed for as long as humanity has existed, but the term “serial killer” was not coined until the mid-1970s by FBI agent and author Robert Ressler. Peering into the depths of pure evil can illuminate a lot of the faults of the human condition and of society in general.
Below is a set of films that refuse to shy away from the evils of humanity, focusing on serial killers from various time periods. If you are itching for your next true crime fix or are just downright fascinated by the immensely macabre, then this list will surely satiate the desires of the iron-stomached viewer.
H. H. Holmes: America’s First Serial Killer (2004)
Chicago, 1893. The World’s Fair was gearing up into full swing and people flocked from far and wide to see visions of the near-future. Yet, something sinister lurked in the streets of the windy city and preyed on these tourists. Herman Mudgett — aka H.H. Holmes and also sometimes known as the Torture Doctor — designed and built his own hotel full of torture chambers and various tools of death and suffering. He rented the hotel’s rooms out to visitors of the world’s fair, and he brutally murdered them. The documentary H. H. Holmes: America’s First Serial Killer chronicles Mudgett’s entire life in an attempt to explain his serial killer ways, and the film itself is interwoven with on-location footage and many reenactments. It does not play its cards close to its chest; instead, it invites the viewer into the depraved psyche of one man and how and why he was compelled to prey on those who were in attendance at the 1893 Chicago World’s Fair.
Conversations with a Killer: The Ted Bundy Tapes (2019)
Ted Bundy is perhaps one of the most famous American serial killers due to just how prolific and evil he was. He kidnapped, murdered, and practiced necrophilia, and once caught, he confessed to 30 homicides between 1974 and 1978. He was (and still is) a notorious figure, and during his trial, he garnered a sort-of cult following because people found him both handsome and charming. He was a narcissist who knew this, and he weaponized his self-image to lure in possible prey and, when put on trial, to garner sympathy. Joe Berlinger‘s Netflix documentary Conversations with a Killer: The Ted Bundy Tapes is a fascinating peek behind the myth of Bundy, and through interviews featuring Bundy on death row and other reels of found footage, the myth becomes self-immolated and the viewer sees the man for who he really was. A monstrous man whose narcissism and self-hubris knew no bounds; he waxes philosophical but never really manages to say anything at all.
Unmasking Jack the Ripper (2005)
Jack the Ripper has long been one of the most famous serial killers because he was never caught, and his reign of torment around the Whitechapel district of London in 1888 has become notorious for just how violent it was. Unmasking Jack the Ripper both attempts to put a face to the murderer and to fill the viewer in on every single detail about the Jack the Ripper killings. It is meticulously detailed and filled with decent reenactments. Although it may be just a documentary made for television that does very little for the documentary form, it is the details within the film that makes it such a compelling (and unsettling) watch. Check it out via YouTube:
Albert Fish: In Sin He Found Salvation (2007)
Albert Fish is a relatively little-known serial killer among modern true crime connoisseurs. The film Albert Fish: In Sin He Found Salvation proves that he is one of the most disturbing and fascinating serial killers to have ever lived. He was an elderly man who preyed on children in Depression-era New York City, and he practiced both cannibalism and sadomasochism. He was compelled to murder and to maim due to the fact that he took many of the more violent tales found in the Bible all too literally. In his eyes, he was conducting the work of God. John Borowski‘s documentary features interviews, photographs, and footage of the era in order to paint a picture of the monster that was Albert Fish. Furthermore, the film also uses multiple reenactments of Fish’s murders in order to show, in detail, how vile he truly was. Yet, the violence is never played for shock value — the doc is more interested in the man and his psyche than it is with his murders.
Tales of the Grim Sleeper (2014)
Tales of the Grim Sleeper is a documentary directed by Nick Broomfield with his son, Barney Broomfield, and Marc Hoeferlin, and their lens is set on Lonnie David Franklin Jr., akaThe Grim Sleeper. Traditionally, Nick Broomfield has tended to have an onscreen presence in his films, but here he curbs that technique in order to literally recede into the background, which is great since the content of the film truly speaks for itself.
Franklin was convicted of killing 10 people (though many believe the count to be upwards of 100) in the Los Angeles area between 1985 and 2007. He was dubbed The Grim Sleeper due to the fact that he took a 14-year break between his crimes, from 1988 to 2002. The film is focused on the man as a catalyst for horrific crimes, but the loose and subjective documentary is more interested in the lives he ended, ruined by proxy, and with just how the LAPD let the killings go on for so long. Thus, the filmmakers do not seek to answer the whys and hows of The Grim Sleeper and his killings but rather how the failings of the criminal justice system and a racist police force let him get away with his killings for so long. It is a film rooted in the past — in previous actions and events — but the systemic apparatus that engulfs every ounce of the film is deeply rooted in the present. Tales of the Grim Sleeper is a thought-provoking documentary that takes a unique look at the eponymous serial killer and the ripple effects that they can have on society, and vice-versa.
The Jeffrey Dahmer Files (2012)
The Jeffrey Dahmer Files is a documentary that plays with the apparatus of documentary itself. Jeffrey Dahmer needs no introduction for he is one of the most famous American serial killers, if not the most famous. During his time as an active serial killer, he raped, murdered, and dismembered 17 boys and men. He also participated in cannibalism and an act of preserving body parts and bones of his victims. How this film plays with the documentary form is in how it is structured and in how its story is told. It features the usual talking-head interviews and archival footage that can be found in most docs, but it also features dramatized segments of scenario-based storytelling that act to flesh out Dahmer as a man, as a monster, and a myth.
Rather than trying to answer why Dahmer did what he did, The Jeffrey Dahmer Files meticulously lays out the details of his life and murders as well as bringing the utter weirdness of some of his actions to light. For example, in one of the dramatized scenarios, Dahmer buys a barrel of hydrochloric acid and hauls it home via public transportation. Although the documentary may not offer any new insights about Dahmer, the acted scenes help to flesh out the veil of strangeness that hangs over Dahmer and his depraved ways.
Cropsey is as much a documentary as it is a genuine horror film. It is perhaps the scariest film on this list due to the fact that it focuses on an urban legend that, as it turns out, is scarily based in tangible actuality. Directors Barbara Brancaccio and Joshua Zeman aim to find out why the Cropsey legend exists and where it hails from. The Cropsey myth itself is based in Staten Island and is about a boogeyman-like figure that stalks and takes refuge in the remnants of the Willowbrook Mental Institution. More or less, the Cropsey myth existed to keep kids out of the old and dilapidated building. Yet in 1987, Cropsey became real. Jennifer Schweiger, a child with Down syndrome, was abducted; never to be seen again.
Schweiger’s disappearance and other children’s disappearances are tied to a man named Andre Rand, an individual who once was a patient at Willowbrook. His presence in the film seems to be Cropsey made manifest. The documentarians reach out to him in prison and they even trek into the woods of Staten Island to walk through the remains of the hospital. It is here where documentary slips into horror and a palpable sense of tension and unease is felt as the filmmakers walk through the hospital and its surrounding woods. Cropsey is an endlessly fascinating documentary that plays with genre form while never giving the viewer any easy answers. Good luck sleeping after watching it.
The Town that Dreaded Sundown (1976)
The original version of The Town that Dreaded Sundown may seem like an odd choice for a list such as this. But hidden deep within and in plain sight of this low-budget horror film is a work that exists between fiction and fact — through freeze frames, specific dates, and fact-based voiceover, the film becomes part documentary. Although what is shown on screen is somewhat accurate at times and wholly inaccurate at others, there is no denying that it plays with the documentary genre form in interesting ways.
The Town that Dreaded Sundown is focused on a string of random killings that occurred in 1946 in the town of Texarkana, Texas. A hooded figure — dubbed the Phantom Killer — attacked eight people (five were killed) in and around the Texarkana area. The killings caused an uproar in the small sleepy town, as post-war America seemed full of promise, a far cry from horror. It is a little-known story that deserves better visual documentation than what is offered in this film, but the compelling nature of the utter weirdness of the filmmaking on display in The Town that Dreaded Sundown and the true crime nature of its documentorial aspects makes it a compelling and intriguing watch.
This is the Zodiac Speaking (2008)
This is the Zodiac Speaking is a documentary directed and compiled by David Prior about the ever-famous and still-unsolved Zodiac killings that struck fear in the people of Northern California during the late 1960s and early 1970s. As a documentary, it plays dryly true to form, as it is solely compiled of interviews with survivors of the killings and the surviving investigators involved with the case. Although it may be dry in form, it is immensely rich in its thematic density and factual aptitude. Most, if not all, facts of the Zodiac cases are laid bare and stripped to their essential elements, spoken of in detail, and looked at again with new points of view. While it may not answer the question of who the Zodiac killer is, it offers enough rich factual detail to leave any true-crime fan interested in serial killers wholly satisfied.
Aileen: Life and Death of a Serial Killer (2003)
Aileen: Life and Death of a Serial Killer is possibly the greatest documentary ever made on the subject of serial killers. Nick Broomfield‘s documentary acts as a sequel and final act to his revelatory 1992 documentary Aileen Wuornos: The Selling of a Serial Killer. This film is even more interested in Wuornos as a person and how she perceives her crimes. Through the filming of several interviews with her, Broomfield affords the viewer a startlingly intimate look at the person dubbed “the world’s first female serial killer.” And it is through this closeness and personal reflection that Broomfield’s film shines brightly.
Wuornos was charged with killing seven men in Florida between 1989 and 1990 by shooting them to death at point-blank range. Her crimes became infamous and so did she. She was convicted of six of the murders and sentenced to death by lethal injection. But could her story have had another ending, one that did not involve the death penalty? Broomfield seems to believe so and his documentary argues for it. Through Wuornos’s case, he builds a firm argument against the death penalty and shows her as inarguably human. Yes, she was guilty, but she was also a woman who was fractured and beaten by life. She should have been deemed legally insane and admitted into an institution, and Broomfield’s footage of her makes this abundantly clear. Her eyes and her visage tick and dart back and forth with the menace and fear of a cornered animal, but through it all, there are brief illuminations of the human being underneath it all.