For some readers, the edgiest thing they’ll cozy up to is a murder mystery solved by a cat. For others, however, a kitty conundrum just won’t do. If you’re seduced by the grittier side of literature, we recommend the list of dark books below—all of which contain disturbing, subversive stories you'll be thinking about long after the final page.
Last Exit to Brooklyn
The cult classic features a brutal and frank portrayal of lower-class life in Brooklyn, including domestic violence, gang rape, and an uncensored look at prostitution and transvestism. Like other books on this list, Last Exit to Brooklyn is actually the subject of an obscenity trial.
The Mad Man
This pornographic tale—or as the author calls it, “pornotopic fantasy”—follows young graduate student John Marr in New York as he balances his academia with wild nights of anonymous sex with homeless men in bathroom stalls full of spent needles. As the narrator explores more and more unconventional sexual urges, Delany attempts to both shock and educate his readers about homosexual life in the ‘70s and ‘80s. You can go even darker with his novel Hogg, about a trucker who is paid to rape strangers.
The Story of Junk
Witty, terrifying, and utterly cool, Yablonsky’s roman à clef is a searing, hyperreal account of the heroin underground in 1980s Manhattan. Library Journal compared the novel to “a grisly car accident that you can’t tear your eyes from.”
The Downtown Eastside in Vancouver, Canada, is about as close to urban hell as you can get in the Western Hemisphere. Yet in this cauldron of drugs, shattered dreams, and extreme violence, Tom Bauer and his girlfriend, Paulie—both ex-junkies and parents of baby Melody—are trying to make a life for themselves.
The city of Boston banned Beat writer William S. Burroughs’s Naked Lunch for portraying unrepentant drug use, child murder, and pedophilia. The ban was overturned, because of the book’s social value, based on the testimony of both Allen Ginsberg and Norman Mailer. The book infamously protests the death penalty and experiments with non-linear narrative styles.
A Clockwork Orange
A Clockwork Orange is a dark and gritty dystopian work. It follows Alex, a sadistic gangbanger, as he and his “droogs” perform unspeakable acts of violence. He is caught and made to undergo government aversion therapy before being re-released into the streets with severe complications. Now known as one of Time’s 100 best novels, it is often banned and was once repudiated by its author.
Tropic of Cancer
Henry Miller’s semi-autobiographical tale of a homeless writer’s bawdy adventures in Paris never shrinks from explicit detail. The mix of offensive language, vignettes, and aggressive social commentary led to the book’s immediate ban. As a judge at Miller’s obscenity trial raved, “It is a cesspool, an open sewer, a pit of putrefaction, a slimy gathering of all that is rotten in the debris of human depravity.”
Related: 40 Scariest Books of the Last 200 Years, from The Lineup
The Virgin Suicides
The title says it all in this dark and despairing tale of five Catholic sisters who commit suicide within a year of one another. Told from the collective point of view of a group of boys who obsess over the melancholy sisters, this tale is intense and eerie from start to finish.
Falconer is the story of a university professor and drug addict named Ezekiel Farragut. He’s at Falconer State prison for the murder of his brother and barely clinging to his humanity. As he wallows in his mistakes and starts an affair with a fellow prisoner, author Cheever explores what it really means to be an American man.
A Good Man is Hard to Find
Unlike our other picks, A Good Man Is Hard to Find is a collection of short stories. Taken as a whole or individually, they present a pretty dark view of the world. Jarring moments of violence, greed, and apathy all work together to paint a bleak mural of humanity at its very worst.