Inside the minds of 5 chilling literary psychopaths

Дата публикации: 16-07-2026 14:30:00

Literature explores the breadth of human experiences, even those behaviors and thoughts we find abhorrent. Characters who are cruel, malicious, and heartless are typically the villains of the story. They stand in opposition to a protagonist who, while perhaps flawed, is heroic, selfless, and kind — qualities we value and admire. When it comes to spending time with one character type or the other, it’s obvious which one readers prefer. 
But sometimes, storytellers want to center their tale on the type of person we wouldn’t want to pass on the street, much less inhabit their point of view. These characters may even be the protagonists of their story in spite of — or because of — their distasteful personalities.
The down low on the low-down
Before diving in, it’s worth clarifying what psychopathy actually is. While words like psycho and psychopath get thrown around a lot, they are often used as insults, a quick-fire way to label someone unstable or weird. Even the more clinical psychopathy can be overly stigmatizing, which is one reason the term hasn’t been included in professional diagnostic manuals since 1980. Mental health professionals today prefer to categorize related diagnoses, such as “antisocial personality disorder,” more on behavior than personality traits. But while some argue that psychopathy is a useless diagnosis, it remains one of the most discussed personality disorders.
It is also fiendishly difficult to assess because its dimensions exist along a broad spectrum. The most widely used diagnostic tool, the Hare Psychopathy Checklist-Revised (PCL-R), looks at 20 personality traits. These include grandiosity, pathological lying, superficial charm, criminal versatility, and other nasty attributes. To complete the checklist, a doctoral-level clinician must conduct a face-to-face interview that can last for up to two hours.
Thankfully, as readers of fiction, we don’t need a 20-point checklist to make a rough determination as to whether a fictional character is psychopathic. A simpler model breaks the disorder down into three specific traits. Those being:
Disinhibition (impulsivity, high risk tolerance, and a reckless disregard for safety).
Boldness (extreme self-confidence and egocentrism paired with a need to be socially dominant).
Meanness (a lack of empathy, exploitative tendencies, and no remorse for harming others). 
More subjectively, though perhaps more illustratively, Robert Hare, the psychologist who developed the PCL-R, described psychopaths as:
“[…] social predators who charm, manipulate, and ruthlessly plow their way through life, leaving a broad trail of broken hearts, shattered expectations, and empty wallets. Completely lacking in conscience and in feelings for others, they selfishly take what they want and do as they please, violating social norms and expectations without the slightest sense of guilt or regret.”
With these dimensions in mind, let’s turn to some of literature’s greatest psychopaths*. Spoilers ahead.
Stained glass depicting Richard III and Queen Anne, Cardiff Castle, UK. (Credit: Wikimedia Commons)
Richard III in Richard III (Late 16th century)
[W]hen thy warlike father, like a child, / Told the sad story of my father’s death, / And twenty times made pause to sob and weep, / That all the standers-by had wet their cheeks / Like trees bedash’d with rain: in that sad time / My manly eyes did scorn a humble tear
William Shakespeare’s characters wrestle with madness, psychological crises, and all manner of unhealthy obsessions, so it’s no surprise that at least one among their ranks would be a psychopath. His oeuvre has a few standout candidates actually — Iago from Othello comes to mind — but Richard III is the handily best of the Bard’s worst.
Richard III is a Machiavellian schemer with eyes on the throne. He plots to marry Lady Anne despite being responsible for the death of her husband, the heir apparent, Edward of Westminster. He lets his brother, the Duke of Clarence, be arrested for treason and later orders his assassination. He kidnaps two princes and has them killed. After marrying Lady Anne, he has her poisoned so he can pursue a different woman. The list of ill deeds goes on.
The death and misery Richard III engineers win him the throne, but his reign is short-lived. The play ends at the Battle of Bosworth Field, where Henry Tudor, Earl of Richmond, slays Richard and claims the throne as Henry VII.
After reading or watching the play, it’s not difficult to spot Richard III’s psychopathic traits. He can’t relate to others and lacks empathy. In one speech, he seems pleased by how much pain he caused another person. He is a pathological liar, using his charm and eloquence to fool almost everyone. He also seems more than a little reckless. In his famous opening soliloquy, he announces he is “determined to prove a villain” because he’s bored. While he does have his moments of guilt, these don’t slow him down much.
It’s worth noting that while the play is often categorized as a history, covering the end of the War of the Roses, Shakespeare takes more than a few artistic liberties in his villainous portrayal of Richard III. The monarch was no saint, but there is no actual evidence that he orchestrated the deaths of King Henry VI, Lady Anne, or the two princes. Shakespeare’s exaggerations likely stemmed from his writing during the reign of Elizabeth I, whose grandfather was none other than Henry VII.
Amy Dunne in Gone Girl (2012)
‘My gosh, Nick, why are you so wonderful to me?’ He was supposed to say: You deserve it. I love you. But he said, ‘Because I feel sorry for you.’ ‘Why?’ ‘Because every morning you have to wake up and be you.”Gillian Flynn’s Gone Girl is a mystery-thriller about the disappearance of Amy Dunne, the quintessential beautiful blonde housewife. During the investigation, suspicion begins to fall on her husband, Nick, when it is discovered he is in extreme debt and increased Amy’s life insurance shortly before she vanished.
The novel shifts between Nick and Amy’s perspectives to reveal two deeply troubled people caught in a bad relationship. Structurally, this means the duo plays double duty: at times, they serve as the protagonist while also being each other’s antagonist. But Amy is hands-down the more psychotic of the two.
You see, Amy wasn’t murdered. After learning that Nick was having an affair, she staged her disappearance as revenge and fabricated clues that would frame Nick for her death. She jacked up his credit card debt, suggested the life insurance policy change, and forged diary entries that characterized Nick as a violent and abusive husband. She even plants her own blood as evidence and, at one point, plans to drown herself to ensure Nick receives the death penalty.
As the story progresses, it is revealed that Amy has a history of blackmailing people while playing the victim. She has no qualms over harming others, even killing her old boyfriend, Desi. And while we can’t say she is impulsive — she really takes her time planning her revenge on Nick — she certainly lacks empathy, is egocentric, and has a high-risk tolerance.
Part of the novel’s appeal lies in how it explores the psychopaths’ use of charm to exploit others. Amy is well aware of how the public at large views women like her (the so-called “missing white woman syndrome”). The media show no interest in investigating the truth, only confirming people’s biases and preconceived notions for ratings. But the person they are fawning over is the one manipulating them to her own ends.
The poster for the 1926 silent film adaptation of The Great Gatsby, starring Warner Baxter as Gatsby. (Credit: Wikimedia Commons)
Jay Gatsby in The Great Gatsby (1925)
I’ve always been glad I said that. It was the only compliment I ever gave him, because I disapproved of him from beginning to end.
F. Scott Fitzgerald’s classic takes us to the jazzy, gin-fueled decadence of the mid-1920s. Well-known for exploring the emptiness of wealth, class struggles in the United States, and the darker side of the American dream, the story features an abundance of objectionable characters, and the eponymous Gatsby is one of them. He may not check all of the PCL-R’s 20 points, but he definitely sports more than a few psychopathic traits.
While Nick Caraway, the novel’s narrator, is infatuated with him, Gatsby is up there with Richard III in his gift for lying. The man lies constantly. Even when Nick points out some of his more glaring contradictions, he responds with more lies. Gatsby’s motivations are complex, but basically, all the lying comes down to either a desire to control how others see him or to hide the mysterious source of his wealth — later revealed to be bootlegging (with hints suggesting his involvement in more unsavory dealings).
His obsession with Daisy Buchanan, Nick’s second cousin and wife to the odious millionaire Tom, is in part due to her being the first woman he couldn’t immediately charm. After returning from the war, he proceeds to stalk her and convince her to abandon her family. He is the kind of man who will go to any lengths to get what he wants — even if it means dehumanizing and hurting others.
That said, Gatsby does appear to form reasonably deep emotional connections; is capable of non-impulsive behavior; and is willing to take the fall for Daisy’s hit-and-run rather than flee to avoid prosecution. He may not be as strong a candidate for psychopathy as the others on this list, but that just goes to show that in literature, as in real life, people are complicated.
John Wayne Cleaver in I Am Not a Serial Killer (2009)
“If you met me on the street you’d never guess how much I wanted to kill you.”Our next entry, written by Dan Wells, is a real genre-bender. It’s part horror, part thriller, and part coming-of-age novel, but the part we’re interested in is the character study of John Wayne Cleaver. The titular “not a serial killer,” John was diagnosed with antisocial personality disorder when he was 15. As we mentioned earlier, the disorder is not identical to psychopathy — though it does share some overlapping behaviors, such as deceitfulness, a lack of empathy, and a disregard for others’ safety.
Unlike other fictional characters with these traits, John doesn’t ignore or lean into his aptitude for cruelty. Thanks to his fascination with serial killers, John recognizes the traits he shares with history’s gruesome men and sets strict rules to regulate his impulse toward violence. He doesn’t allow himself to become obsessed with a specific person, he attends therapy sessions, and he maintains a friendship — even if his care for them is a mere facade.
However, John’s “normal” life is disrupted when a serial killer moves into his small town, and the teen decides to use his morbid knowledge to track the criminal down — an investigation aided by the fact that he lives above the town mortuary, which is owned and operated by his mother. He eventually learns that his neighbor, Mr. Crowley, is the killer. More specifically, Crowley is a demon who needs to harvest the body parts of others to replace his own deteriorating body. Did we mention that this one gets weird?
But what makes I Am Not a Serial Killer an interesting inclusion for a list like this is the characters. Crowley is a sympathetic villain, and so is John despite, what we know about his thoughts and feelings for others. By the end, John uses the experience to try to grow and make genuine connections with the people in his life, which is not how these psychopathic stories typically end.
A scene from the stage production of The Twelve Chairs, the Theatre Center Na Strastnom, Russia. (Credit: Wikimedia Commons)
Ostap Bender in The Twelve Chairs (1928)
“Oh-ho! If you’ve gone ahead and opened a personal account for me, then the least you could do is tally it right. Start up a debit column, start up a credit column. Don’t forget to enter the sixty thousand rubles you owe me in the debits, and the rest can go in the credits. The balance is in my favor: 59,992 rubles.”
Speaking of endings, let’s end this list on a lighter note. The Twelve Chairs is a hilarious Soviet-era novel by Ilya Ilf and Evgeny Petrov. It satirizes the USSR’s New Economic Policy and Russian life in general while telling the story of a hunt for one dozen matching chairs.
During the Russian Revolution, Kisa Vorobyaninov’s mother-in-law hid the family’s gems in a chair from her dining-room set to keep them safe from the Bolsheviks, but the Communists wound up confiscating all of her personal property anyway. On her deathbed, she tells Kisa about the treasure hidden in one of the 12 identical chairs, and Kisa sets out to retrieve the family’s lost wealth. The con man Ostap Bender joins Kisa in his search, and the two travel the USSR, having all sorts of humorous misadventures and team-ups along the way.
None of the novel’s characters are upright citizens, but Ostap may be the worst of a bad bunch. Highly manipulative, he more or less forces Kisa into working with him. He is also focused on the short term, frequently turning to scams or brute force to keep people motivated. A successful criminal, he has no problem lying, parting marks from their money, and abandoning those he no longer needs. While he does have some empathy for those he works with, it isn’t enough to improve his behavior. 
If anything, the reader’s knowledge that he does have some sense of right and wrong might even make him seem worse. And Ostap’s unwillingness to curb his poor behavior proves his undoing. He is ultimately murdered by an alienated Kisa shortly before they discover the final chair. 
In fact, few of our psychopathic protagonists meet desirable fates. Three of the five are killed, and Amy Dunne remains stuck in a loveless marriage. Only John, who actively works against his darker impulses, enjoys what we may consider a happy, if traumatic, ending. This suggests that one reason writers choose to center their stories on characters with such distasteful personalities is to serve as a warning: those who live in meanness, boldness, and disinhibition do harm not only to their victims but also to themselves.
* Editor’s Note: Yes, Patrick Bateman from Bret Easton Ellis’s American Psycho (1991) obviously meets the criteria, and no, we didn’t include him. That one just felt a little too easy.
This article Inside the minds of 5 chilling literary psychopaths is featured on Big Think.

Схожие новости

#	Наименование новости	Тональность	Информативность	Дата публикации
1	The psychology of morality, perversion, and revenge, in 67 minutes	0	7	17-07-2026
2	2 ways to deradicalize someone (and the 1 that works the best)	0	5	17-07-2026
3	The Long Vendetta	0	5	29-05-2026
4	CHARACTER 101: A round-up of advice from bestselling authors on creating compelling characters, from Isabel Allende to August Wilson	0	5	17-09-2025
5	TOP TEN WRITER’S QUOTES TO LIVE BY	5	4	20-05-2026
6	12 Juicy Hollywood Tell-Alls That That Will Change How You See Fame	2	6	30-06-2026
7	BEHIND THE PAGES: THE MUDFLATS MURDER CLUB	0	5	11-08-2025
8	Night Howl	0	5	24-06-2026
9	Troubled son accused of killing mom in posh NY town was ‘off and weird’ since grade school, classmate reveals	-2	6	10-07-2026

Классификация: Мнения. Схожих патентов: 0. Схожих новостей: 9. Тональность: 0. Информативность: 5. Источник: bigthink.com.