Writing the Literary Psychopath

We all know that unrepentantly evil characters are the most fun to write. But how do you make a psychopath memorable, and more than just the tired one-dimensional shock value trope of airport novels?

Make them a literary psychopath: a well-written, believable character that isn’t just a diabolical all-knowing plot device.

Having read far too many books featuring them than is probably healthy, I’ll focus on three—Humbert Humbert of Lolita, Patricia Highsmith’s “The Talented Mr. Ripley,” and for gender balance, Lilly Dillon from Jim Thompson’s The Grifters (watch the movie! Anjelica Huston rocks the role). For bonus reading, Thompson’s The Killer Inside Me features the stone-cold scary narrator Sheriff Lou Ford.

What is a psychopath?

For purposes of brevity, see Robert D. Hare’s Psychopathy Checklist-Revised (PCL-R), considered the definitive criterium.

Both psychopathy and sociopathy are classified as anti-social personality disorders. There’s a lot of debate among mental health professionals on whether “sociopath” is an outdated term or not. Here’s one perspective on the differences.

Some basic tenets about the literary psychopath

Part of the excitement of a psychopath is his or her unpredictability. Yours doesn’t have to be everything on this list.

Psychopaths don’t seem so bad compared to other characters who also lack true north on their moral compasses. Humbert is self-delusional, deceitful and morally bankrupt. However, Nabokov satirically sets him against Ramsdale’s college town intelligentsia who are all hypocritical, competitive, petty, childish, selfish, manipulative bourgeois poseurs who commit offences against intellect and taste. Think Charlotte Haze and her faux-European airs. And Humbert never subjected Lolita to orgies and acting in porn films like Clare Quilty did. In contrast, Humbert acted out of what he claims is pure love and adoration.

In Ripley, Dickie Greenleaf’s only contributions to the world are his bad paintings. He is a lazy and ungrateful son who won’t visit his dying mother. Tom Ripley, on the other hand, writes the Greenleafs warm letters and acts more like the dutiful offspring. Marge, Tom’s rival for Dickie, is described cruelly, with a “gourd-like” physique and an “ugly” voice. She loses any sympathy we might have had when she sells photos of her life with Dickie to a scandal-rag newspaper.

Every character in The Grifters, save for the nurse, is a cheat and a con. Lilly at least gets points for getting care for her son Roy after he is hospitalized.

Give them some redeeming characteristic(s). Highsmith recommended “giving the murderer-hero as many pleasant qualities as possible—generosity, kindness to some people, fondness for painting or music or cooking, for instance. These qualities can also be amusing in contrast to his criminal or homicidal traits.” Let some sane, “good” characters consider the psychopath their friend.

The psychopath knows when they are putting on an act. That raises tension for the reader. Knowing what the character is really like forces the reader to make a moral choice: put the book down in outrage, or keep reading and be a complicit witness.

The psychopath is self-loathing under the bravado. We meet a Humbert who claims he’s matinee-idol material. By the end, he’s calling himself a massive, ape-like “cesspool” and “monster.”

The psychopath feels fear—but only of being caught or punished. Psychopaths have a stunted moral development and childlike determination of right and wrong. Yours should operate in terms of obedience and punishment: pleasant or unpleasant consequences (“If I do something bad, I might get caught”); or in terms of the size or power of those who impose the rules (“The big mean policeman will put me in jail if I do something bad.”).

The horror of the psychopath’s acts come from their matter-of-factness. There is a chilling simplicity in many effective murder scenes, almost like watching TV with the sound turned off. There is no excessive gore or extraneous emotion. The deaths can be nasty, and the killer can react, but the scene should have a certain amount of objective distance. In first-person novels, some psychopaths assume an almost Victorian level of modesty and don’t fully describe what they did. In many cases, there is no buildup to the murder—the psychopath just kills without warning.

Psychopaths kill the ones they love. It takes an extremely sick person to do that. Readers know this.

The psychopath doesn’t live exclusively by cunning. The psychopath lives in the wider world, and not everyone is smart. Coincidences happen, too. Would Ripley have gotten away with Dickie’s and Freddie’s murders if not for the ineptitude and laziness of the Italian police?

Some guidelines for writers

As the creator of a psychopath, you have a wide canvas to paint. Here are some general observations on how to do that well.

Write to portray, not to judge.  Highsmith advised “creative people do not pass moral judgments—at least not at once—on what meets their eye. Art essentially has nothing to do with morality, convention, or moralizing.”

Let them tell the story. Show readers your psychopath’s interior life—all their thoughts, doubts, cunning and overreactions. First-person narrators win readers’ trusts easily.

Certainly, psychopaths do not make reliable narrators. They often interrupt their story to swear to the reader they are telling the truth. Oftentimes, this also allows the character to convince himself this is how it happened.

If telling the story in the third person, keep it close on the psychopath. Even the second person point of view has its uses. Thompson used it in a few of his books to notably to portray psychotic breaks.

Stack the deck in your psychopath’s favor.  Give your psychopath a socially-acceptable job so they can move in the darkness easily: college professor, doctor. Put your killer in a small town with spotty internet, bumbling police, and where nobody locks their doors. Better yet, have no police presence whatsoever, like Thompson does in The Grifters.

Give the psychopath a doppelganger.  The psychopath needs a double (real or imagined) to be the mirror that he or she cannot bear to look into. So—spoiler alert—the psychopath usually ends up killing this person too. When your character breaks that mirror, ironically, clarity or success occurs. After Humbert murders Quilty, he reveals, in harrowing detail, that he knew the whole time that his exploitation of Lolita was destroying her. Roy Dillon’s girlfriend Moira looks a lot like his mom, a fact which Lilly exploits to escape. Dickie is the man Ripley both loves and wants to be.

End the story on a bang, but keep it unresolved.  Lolita ends on a long sob of grief and loss whose full impact cannot be felt unless the reader knows enough to return to that seemingly insignificant “biographical note” about Mrs. Richard Schiller. Lilly murders her son, taunts his body one last time, and sashays off with the cash.

Finally, have fun with your psychopath. So says Highsmith: “It is possible to make a hero-psychopath 100% sick and revolting and still make him very fascinating for his very blackness and all-round depravity . . . if the book is entertaining, there is no reason why the reader should have to ‘like’ the hero. If there must be reader-identification, a term I am rather tired of, then provide the reader with a lesser character or two (preferably one who is not murdered by the hero-psychopath) with whom he can identify.” Then again, Highsmith acted as if Ripley was real. She would autograph books as both of them or tell acquaintances that they reminded her of him. Don’t go that far, though, please.

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