The Psychology of the Morally Grey Hero in Classic Literature (Vol. II)

We have established that we love characters who do terrible things. The question that remains — the one that keeps literary critics and psychologists and ordinary readers up at night — is what this love reveals about us. Not about the characters, who are fictional and therefore beyond judgment, but about the readers who return to them, who defend them in arguments, who feel something uncomfortably close to grief when they come to their inevitable ends.

This is the second volume of an ongoing inquiry. The first examined Heathcliff, Rochester, and Dorian Gray. Here we turn to three more figures whose moral complexity has made them among the most discussed characters in the literary canon: Raskolnikov, Gatsby, and the most troubling case of all, Humbert Humbert.

Raskolnikov: The Intellectual's Temptation

Fyodor Dostoevsky's Rodion Raskolnikov, the protagonist of Crime and Punishment (1866), commits murder on the basis of a theory. He has convinced himself that extraordinary men — Napoleons, world-historical figures — are exempt from ordinary moral law. They may transgress, may even kill, if their transgression serves a higher purpose. He is, he believes, such a man. The murder of the pawnbroker Alyona Ivanovna will prove it.

It does not prove it. The murder proves the opposite: that Raskolnikov is not extraordinary, that he is subject to the same guilt and psychological torment as any ordinary person, that the theory was a rationalization for something darker and less coherent than intellectual superiority. The novel is, among other things, a devastating critique of the kind of abstract reasoning that loses sight of the concrete human being.

We are drawn to Raskolnikov because his temptation is recognizable. The fantasy of being exempt from ordinary rules — of being special enough that the usual constraints do not apply — is not unique to murderers. It is a fantasy available to anyone who has ever felt that their intelligence or sensitivity or suffering sets them apart. Dostoevsky understood this, and he made Raskolnikov's punishment not legal but psychological: the slow, agonizing recognition that he is not who he thought he was.

Gatsby: The American Antihero

Jay Gatsby is a fraud. His name is not Gatsby. His Oxford education was a five-month post-war program, not the years of study he implies. His fortune was made through bootlegging and organized crime. His entire identity is a construction, assembled with extraordinary care and maintained at enormous cost, in service of a dream that is itself a kind of fraud: the belief that the past can be recovered, that love can be purchased, that the green light across the bay can be reached if you only want it badly enough.

And yet Fitzgerald makes us love him. He does this through Nick Carraway, who is himself complicit in Gatsby's mythology, and through the prose, which is so beautiful that it makes Gatsby's dream feel beautiful even as it reveals its emptiness. "So we beat on, boats against the current, borne back ceaselessly into the past." The novel's final sentence is an elegy for Gatsby and for everyone who has ever wanted something so badly that they could not see it clearly.

Gatsby is the morally grey hero as American archetype: the self-made man whose self-making required the abandonment of his actual self, the dreamer whose dream was always already corrupted by the means required to pursue it.

Humbert Humbert: The Limits of Sympathy

Vladimir Nabokov's Lolita (1955) is the most extreme test of the morally grey hero concept in the literary canon. Humbert Humbert is a pedophile and a rapist. He is also, in his own telling, a poet of extraordinary sensitivity, a man of vast culture and genuine aesthetic perception, a lover of beauty in all its forms. He is the most unreliable of narrators, and the novel's central challenge is to read his beautiful prose against the reality it conceals.

Nabokov was explicit about this challenge. He wanted readers to be seduced by Humbert's voice and then to feel the discomfort of that seduction — to recognize that beautiful language can be used to justify monstrous things, that aesthetic sensitivity is not a moral credential, that the capacity to feel beauty does not confer the right to destroy it.

Humbert is not a hero, grey or otherwise. He is a warning about the limits of sympathy — about the danger of allowing a compelling voice to substitute for moral judgment. Lolita is a novel about a crime, and the crime is Dolores Haze's, not Humbert's: the crime committed against her, the childhood stolen, the voice silenced. The novel's genius is that it makes you work to remember this.

What These Characters Share

Raskolnikov, Gatsby, and Humbert Humbert are all, in different ways, men who have constructed elaborate intellectual or emotional frameworks to justify what they want to do. Raskolnikov has his theory of the extraordinary man. Gatsby has his dream of recovered love. Humbert has his aesthetics of the nymphet. Each framework is internally coherent. Each is a lie.

The morally grey hero, at his most interesting, is always a man (and it is almost always a man) who has mistaken his own desire for a principle. The literature that takes him seriously does not excuse this mistake. It illuminates it — shows us how the mistake is made, why it is seductive, and what it costs.

This is the work that only fiction can do: to take us inside a consciousness we would never choose to inhabit, and to bring us back changed.

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