10 Disturbing Interviews with Psychopaths

10 Disturbing Interviews with Psychopaths

Welcome to WatchMojo, and today we’re counting looking at infamous, unsettling sit-downs with criminals who have been designated full-blown psychopaths.

Gary Hilton (2025)

As boastful as antisocial personalities tend to be after their downfall, countless killers have given interviews behind bars. Few have been as in-depth as Gary Hilton’s conversation with David Scott for a 2025 episode of “Interview with a Killer,” actually titled “Psycho Killer.” This was the National Forest Serial Killer’s first media interview in the 17 years since his conviction for four murders. For roughly an hour-and-a-half, he vividly waxes nostalgic about his crimes, while bragging about being the oldest serial killer on record. And although he acknowledges the irony in taking lives when he himself fears death, he’s eerily detached on the matter. Hilton denies being a psychopath, but experts say that this interview represents a quintessential case.

Angela Simpson (2009)

In 2009 in Phoenix, Arizona, Terry Neely allegedly confided in sex worker Angela Simpson that he was an informant in prison. She later spent three days torturing the physically handicapped man to death. She claimed fame in prison through a local news interview in which she both embraced her fate and expressed no remorse. That much humility was absent from the post-arrest police interview featured on “Signs of a Psychopath.” Experts say Simpson’s graphic, gleeful confession exemplified the docuseries’ title. Though she was never formally diagnosed as a psychopath, she’d been receiving clinical psychiatric treatment since she was 10 years old. With no hope of getting out of prison, Simpson now seems eager to discuss her warped principles with the media.

Arthur Shawcross (2008)

The case of the Genesee River Killer faced immense controversy due to his initial conviction for manslaughter, despite a diagnosis of schizoid personality disorder. Arthur Shawcross murdered around a dozen more people while on parole. It seemed obvious to the world that he was a monster from his 2006 interview for the docuseries “Most Evil.” The 2008 documentary “Interview with a Serial Killer” allowed him to discuss his murders and unconfirmed cannibalism in sick detail. Through it all, he maintains the approachable demeanor of someone’s wholesome grandparent. But there was nothing wholesome about his story. Since his death in 2008, Shawcross has been widely recognized for his ability to charm the system into overlooking profound evil.

Dr. Harold Shipman (1982)

Disturbance is sometimes especially potent when mixed with hindsight. A 1982 episode of the current affairs program “World in Action” covered the London out-patient psychiatric service Brindle House. Among the healthcare professionals interviewed was the renowned Dr. Harold Shipman, who praised community-based mental healthcare as more humane than hospitals. Eighteen years later, he was convicted of murdering 15 patients. A follow-up inquiry implicated him in more than 200 murders, making him one of the most prolific serial killers in history. Transcripts and audio recordings of Shipman’s evasive police interviews have since been studied for the personality indicators of psychopaths in respectable positions. It’s no less harrowing to look back at this man acting as an authority on caring psychiatric treatment.

Richard Ramirez (1991)

The Night Stalker has long bewildered the public as one of the darkest killers to invade American media. His interviews on death row offered little true insight into how someone could take so many lives. One of the first was given via satellite for “The Maury Povish Show” the day after his abusive father’s death in 1991. Audiences witnessed and interacted with Richard Ramirez as he argued that environmental factors agitate a natural capacity for murder. But his cold tone, irreverent disposition and refusal to comment on motive suggest something deeper. This was consistent across Ramirez’s media interviews throughout the ‘90s. The one with Povich, as well as an episode featuring survivor Ginny Petersen, still stand out for confronting the worst of humanity.

Aileen Wuornos (2001-02)

Shortly before her execution in 2002, Aileen Wuornos was formally diagnosed with severe psychopathic traits. It was around this time that she was meeting with Nick Broomfield for the documentary “Aileen: Life and Death of a Serial Killer.” After waiving all appeals, she admitted that her seven killings were not in self-defense, and that she should be executed. In the last interview, however, she claimed that this was a false confession brought on by exposure to “sonic pressure” installed in her cell. One way or another, it was apparent that her mental health was in decline. Broomfield’s record of Wuornos’s unstable demeanor and story is one of the most harrowing images of a serial killer faced with their own mortality.

Paris Bennett (2019)

In 2007 in Abilene, Texas, Paris Bennett claimed that he killed his little sister Ella during a delusional episode. It was quickly determined that the 13-year-old actually premeditated the murder to spite their mother Charity over her substance use disorder. He had thought about killing before. Twelve years later, the now-grown Bennett granted his first media interview to Piers Morgan for a series on convicted criminals. “Psychopath with Piers Morgan” affirmed Bennett’s prior diagnosis through his detached disposition, lack of remorse, and vivid account of the crime that broke his mother. All the while, Charity watches on a monitor as her son’s inexcusable cruelty is exposed to the world. The two ceased communication shortly thereafter.

Richard Kuklinski (1992)

Did the New Jersey and New York underworld really fear the name “The Iceman” until his downfall in 1986? The public was baffled by Richard Kuklinski’s ability to separate his criminal enterprises from his suburban family life, especially after HBO aired his chats with Arthur Ginsberg in 1992. “The Iceman Tapes” continued in 2002 and 2003, as Kuklinski claimed that his enterprising bloodshed went beyond the five murders he was in prison for. However, there has been no confirmation that he worked as a mafia contract killer. Psychiatrists determined that his claims were undermined by psychopathic traits like a tendency to exaggerate. To whatever extent Kuklinski used his condition for profit, his stories are surely the product of a disturbed mind.

Charles Manson (1989)

This California cult leader who ordered a murder spree in 1969 was never one to turn down attention. But with his controlling nature, Charles Manson wasn't willing to grant media interviews until the 1980s. Even then, bizarre and obtuse statements offered little insight into his seemingly fragile psyche. Perhaps the most notorious demonstration of it now is from an interview for the short-lived “National Report” regarding the 20th anniversary of his crimes. When asked to describe himself in one sentence, Manson frantically contorted his face, said that he was “Nobody,” and made violent threats. While this moment and the altogether twisted segment are remembered more than “National Report” itself, there's ample evidence of Manson’s volatility from interviews alone.

Paul Bernardo (2007)

Legal restrictions on prison interviews in Canada have limited media access to Paul Bernardo. There may be enough said in the public footage of his 2007 police interview regarding the 1990 disappearance of Elizabeth Bain. He denies that she was among the assaults and murders he committed before his arrest in ‘93, which he described as “mistakes.” Bernardo spends most of the 31-minute session playing the victim of institutions that dehumanize him. Whether his points about the justice system are valid, such brazen selfishness and false humility epitomize an antisocial personality. His gestures and ramblings further made this footage an asset in psychopathology studies. But you don’t need to be an expert to be haunted by Bernardo’s obvious disregard for human life.

What are some other haunting interviews with dark minds? Give your evaluation in the comments below.