The best literary novels with criminal protagonists

This classic novel about struggling for redemption after a horrific crime affected me deeply. Raskolnikov’s poverty and radical ideology drive him to robbery and murder.

As a lapsed Catholic, I was gripped by Dostoevsky’s rich exploration of why Raskolnikov did it, examining altruistic Christian ideals alongside new and dangerous notions about the prerogatives of “exceptional” men. The novel virtually invented the crime drama, with the original troubled killer pursued by the original wily detective.

The cast of characters, from the sympathetic Sonya, whose religious faith moves Raskolnikov, to the unscrupulous Svidrigaylov, who embodies irredeemable depravity, is as rich as the play of ideas and the dramatic tension. Powerful on every level. 

I’m fascinated by novels that treat famous real events from an insider perspective.

In this case, it’s the events following the Symbionese Liberation Army’s kidnapping of Patty Hearst in 1974. Fugitive SLA members, including a character based on Hearst, are sheltered by a former radical, Jenny Shimada (based on Wendy Yoshimura), who is also wanted by the FBI in connection with the bombing of draft offices.

Jenny is a sort of house mother to the volatile fugitives, who hope to write a book while in hiding to raise money for their cause, but inevitably she is drawn into their latest dangerous scheme. Filled with brilliant character studies, the novel astutely shows connections between the tortured personalities of individuals and the public acts they commit which end up shaping our culture. 

A masterful book about a tough subject.

Separated from her young son, Romy Hall is serving two consecutive life sentences for killing a customer from the Mars Room, a strip club where she’d been dancing. Brilliantly written with compassion and dry, dark humor, the book explores Romy’s relationships with her fellow prisoners and the despair, dangers, and absurdities of life behind bars.

I loved this novel’s gritty texture, its sentences, its characters, and how it forced me to think more deeply about why and how we incarcerate people. The final sequence in Muir Woods is heart-pounding, wondrous, devastating, and strangely hopeful.

This is a beautifully written psychological thriller.

At a high school reunion, a polite invitation between old friends—Elise, a successful actor, invites Abby, who is floundering, to visit her in LA—spirals into Abby’s attempt to infiltrate the star’s life. The novel fearlessly plumbs the mysteries and complications of friendship and shows how misguided impulses can gradually take over our psyches.

I’m a fan of big endings, and this novel’s final paragraphs, which cap Abby’s disturbed yet compelling emotional journey, are stunners. 

Raymond Carney—savvy furniture store owner in 1960s Harlem; a small-time, look-the-other-way fence for stolen goods—is one of the most likable criminals I’ve ever read about.

He dreams of moving his young family on up to a nice apartment on Riverside Dr. and scraps for every dollar. His hustling ways occasionally flare into big-time crime or revenge, but his insights into the teeming city are always keen.

Whitehead can do it all: perfectly observed details of the time and place, great characters, wry humor, surprising plot developments, devastating emotional scenes. The implications of race and class are deftly drawn. The prose is gorgeous.

Really, no American writer is better than Whitehead right now. A fun and profound ride.