8 Books Featuring Dangerous, Charismatic Characters

I ’m obsessed with people who are so magnetic, you don’t even notice they’re awful. And in America, I’m hardly alone. It’s not just the current “Summer of the Scam”, wherein the likes of Anna Delvey and the Portofino Pirate are grabbing headlines and everyone’s money. We Americans have always adored the charismatic trickster. Our history is brimming with people who gained fame (or infamy) with little to offer but the ability to make others love and trust them. Maybe it’s because we like knowing that there are at least a few among us who are dodging taxes and responsibility in favor of yachts and first-class travel. Charisma feels more egalitarian than intelligence or beauty or humor: you can’t work for it or be born into it. You simply have it or you don’t.

In my novel The Parking Lot Attendant, I wanted to explore how encountering this quality when you’re young makes it that much more potent, and thus, dangerous. Many readers have told me how much they hate Ayale, how monstrous he is. I see what they mean. But I must admit that much like my narrator, I am at times dazzled by his charm; I too have almost been taken in. And here’s the thing: Ayale uses the skills exhibited by America’s most beloved con men (and women) to make money, get land, and pull a fast one on everyone around him. What could be more blessedly American than that?

Here are 8 books whose protagonists embody this deeply discomfiting relationship between the hypnotic and the horrifying as they lead those around them. (I tried to choose books whose problematic potentates had the potential to fool not only the other characters but we, the readers, as well.)

Swing Time by Zadie Smith

Aimee, the one-name pop star sensation, begins as a mystery. On the one hand, she’s a startling voice of truth for the narrator, a force capable of shocking her out of her lifelong passivity. On the other, she’s condescending, blissfully unaware of her privilege, racist, and oblivious as to how her whiteness and wealth are predatory, destructive and completely at odds with the ideals she claims to uphold. Her manner of dealing with what she perceives to be the narrator’s betrayal reveals what was hidden at the start: Aimee is just as petty and immature as her assistant.

Time Swings Widely

The Great Gatsby by F. Scott Fitzgerald

No one has broken my heart like Jay Gatsby. Much like the narrator, Nick Carraway, we’re tempted to see him as a gleaming example of the American Dream gone great, before we understand that he’s terribly lost and desperate enough to use anyone and everyone to get what he wants. His money is dirty but what takes Jay Gatsby down is his erroneous belief that the amount of money you earn can equal the amount of love you receive.

Dangerous Liaisons by Pierre Choderlos de Laclos

The Marquise de Merteuil is one of my favorite characters of all time. Objectively, she’s a horrible person but my God, has anyone else been this vile with such wit and humor? She despises the weak, the stupid, the religious and the lowbred and, what is perhaps most unforgivable in 1782, she’s a woman who knows what she wants when it comes to sex and can’t think of a single reason why she should be deprived. You can’t help but cheer her on, no matter how duplicitous her tactics, if only because it’s such a joy to see her banter and battle with the best of them.

An 18th-Century Erotic Novel Taught Me All the Wrong Lessons About Desire

A Brief History of Seven Killings by Marlon James

The character of Bob Marley is a host of contradictions: a symbol of freedom; a proponent of lasting change; a contender against the growing western presence in Jamaica; a greedy capitalist; a predator who uses women. Each character has a different impression of and vision for the Singer, whose actions (right or wrong) and thrilling words transform their lives as well as the legacy of their country.

Great Expectations by Charles Dickens

Miss Havisham is not the most pleasant of jilted brides: she raises her ward Estella to be incapable of love and encourages Pip in his passion for Estella and his dreams of wealth, all while knowing that his hopes are for naught. Despite driving much of the plot with her conniving and vengeful schemes, the truth of her tragic love story and the sources of her deep sadness, while not enough to redeem her, make us feel a certain pity for the molting wreck of a woman she has become.

Mao II by Don DeLillo

The writer Bill Gray seems like the kind of author we can get behind (at least in fiction): reclusive, eccentric, well-spoken, resolute in his isolation. However, as events take Bill out of self-imposed solitude to a leading role in international diplomacy, reality gets hazy: is Bill a flawed man who happens to be a great artist? Is he a good writer or simply lucky when it comes to optics? Is he just as astute an opportunist as the Master of the Unification Church or the head of the terrorist cell, whose latest hostage Bill is (kind of) trying to save?

The Secret History by Donna Tartt

When Richard Papen ends up at Hampden College, he falls in with a small group of classicists, led by the inscrutable Henry Winter. Initially, as the shocking events of the story unfold, it seems like Henry is the only selfless and clear thinker of the bunch. Gradually however, as the facts contradict each other and the questions pile up, we’re forced to wonder, is Henry the key to their salvation or the engine of their destruction?

The Neapolitan Novels by Elena Ferrante

Elena Greco and Lina Cerrulo’s friendship is stupendous, cruel, heartbreaking and ultimately, inexplicable. On many occasions, it reads more like a fight to the death than an alliance, and we’re never entirely sure who is manipulating whom, especially since it’s difficult to confirm the accuracy of Elena’s narration. We soon realize that for both, the other woman is the only really worthy opponent they’ve ever met. That wrenching sense of stifled action and dazzling violence, which fuels so much of the books, emerges from observing these two extraordinary people simultaneously attempt to pull each other up and shove each other into the ground.