21 Trangressive Books

by
Daulton Dickey.

Transgressive fiction is a genre of literature which focuses on characters who feel confined by the norms and expectations of society and who break free of those confines in unusual or illicit ways

Without spending too much time elaborating on theories w/r/t transgressive fiction, the above quote is from Wikipedia. Succinct, it offers a broad enough outline to convey the gist of this often ill-defined subset of fiction.

This isn’t a definitive list. It’s also not intended as authoritative. Instead, it’s a list of some transgressive books that have inspired me as a writer—and a person—over the years. Although I should clarify that I don’t love every book on this list. In fact, I find some of them repugnant, their authors appalling, but they’ve still affected me in one way or the other.

If you haven’t read much transgressive fiction, you should do yourself a favor a take a detour into worlds funny and strange, terrifying and awe-inspiring and disturbing.

Although this list deals primarily with fiction, I’ve decided to include a few important works of non-fiction and poetry.

How to Thrive on Rejection: A Manual for Survival by Alan Abel (Barricade Books, 1984)

The least likely book on this list, Alan Abel’s out-of-print gem garners a spot for it sheer outlandishness. This is a record of the exploits of a cunning satirist masquerading as a prankster. 

In one stunt, Abel enlisted several people to populate the audience of talk show host Phil Donahue’s popular daytime program. During the taping, several of Abel’s plants pretended to pass out, causing enough concern that cameras stopped rolling and everyone was removed from the set. While Donahue and crew chalked it up to nervousness at being on a television set and a hot studio, Abel later announced that he had orchestrated the entire thing to draw attention to the vacuousness of television.

In another notorious stunt, Abel managed to get his obituary in The New York Times and enlisted family and friends to play along, persuading people that Abel had, in fact, passed away. Since he was a known prankster, not everyone believed him, so it was no surprise when he emerged to own up to his ruse. One of his admirers and fans, the singular performer Andy Kaufman, admired the stunt and even discussed the logistics of pulling it off with Abel after the truth was revealed.

This is a quick read, at times funny, engaging, and inspiring. Much of the humor, however, feels dated, so don’t expect gut-busting laughter throughout. But at its core, it’s a book about a moralist dissatisfied with the norms permeating an increasingly corporate and media obsessed culture.

While the book itself isn’t controversial or transgressive, it’s included here because it records the exploits of a man who rejected many social norms. His satire contained pointed commentary—and rebellion. Although known as a prankster in his life, we’d now call him a performance artist. He used humor to criticize and attack the conformity of a rule-based society obsessed with media and capitalistic pursuits. The man himself was transgressive.

Great Expectations: a novel by Kathy Acker (Grove Press, 1994)

While this may not rank as Acker’s most transgressive work of fiction, it embodies the motifs recurring through most of her books.

Kathy Acker was a singular writer, equal parts William S. Burroughs, Johnathan Swift, Johnny Rotten, but, most importantly, she exemplified none other than her unique personality and voice.

Reviewing, or even summarizing, a book by Kathy Acker is like trying to review the barrage of tv shows, movies, and commercials as you constantly flip through television channels without pausing to slow down or settle on a single show.

She employed several techniques as a writer—from Burroughs’s cut-up technique to appropriating text from famous writers, to incomplete sections or notes. Combined, these styles produced a hypnotic, hypnagogic effect in the reader while Acker presented characters repulsive and endearing, elusive and narcissistic, prudish and perverse, brooding and full of life.

By eschewing narrative, she created snapshots of people and events. Her books and characters often seemed cold and disjointed. When taken as a whole, however, they conveyed a rare thing in experimental and transgressive fiction: a complex yet beautiful portrayal of the human condition.

A Crack Up at the Race Riots by Harmony Korine (Mainstreet Books, 1998)

This book is nearly impossible to categorize. Neither fiction nor nonfiction, it somehow exists in a state far removed from categorization. (You should note, however, that the title is nonsensical. The book doesn’t have anything to do with race or race riots.)

Produced by les enfant terrible Harmony Korine, writer of the controversial film Kids, writer and director of Gummo and julien-donkey boy. His films were equally as unorthodox as this book. When taken together, however, they convey an aesthetic uniquely Korine’s.

In it’s design and layout, it resembles an avant-garde art book, reminding you of something the Dadaists might have produced. It’s filled with photographs, one-liners, puns, and carries an anarchic vaudevillian spirit throughout.

You can read it in under twenty minutes and dismiss it as quickly. But you’d make a mistake by doing so. As with his films, in A Crack Up at the Race Riots Korine is attempting to introduce us to facets of life we overlook by focusing on the outcast and the downtrodden. For that reason, as obscure as it may be, it’s also a deeply human book.

Fear and Loathing in Las Vegas: A Savage Journey to the Heart of the American Dream by Hunter S Thompson (Random House, 1972)

This book is touted as nonfiction/journalism, but let’s be real: it’s a work of fiction. Sure, it’s based to some degree on real events, but it was formulated, structured, and contrived like any other work of fiction.

Notorious journalist Hunter S. Thompson and fiery civil rights lawyer Oscar Zeta Acosta took a trip to Las Vegas to escape a tense investigation into the murder of famed Chicano Newsman and activist Rueben Salazar.

Their initial trip to Vegas was short. The first part of the book covered the entirety of that trip. But when Thompson set it to paper, he knew he had the beginnings of a great book. Intent on finishing it, he contrived another trip to Vegas with Acosta some weeks later to generate more material so he could finish his masterpiece.

At its core, this book is a lamentation, a dirge to a generation bereft of its former idealism. It follows two men destroying themselves physically and mentally with the help of drug-induced psychosis, as they topple the norms of a society struggling to devolve to the totalitarianism of the 40s and 50s while simultaneously trying to break from that era once and for all. It’s also a transgressive attempt to shatter conventions long codified by establishment journalists. And it’s frequently funny as hell.

Mooch by Dan Fante (Harper Perennial, 2009)

The son of novelist John Fante, Dan is a world unto himself. He’s more akin to Charles Bukowski and Hubert Selby, Jr. than to his father.

You won’t find romanticism in Fante’s works. Instead, you’ll find alcoholism, drug abuse, and madness—themes drawn from Fante’s decedent and depraved life.

Mooch follows Fante’s fictional avatar, Bruno Dante, as he attempts to leave a halfway home, carve out a respectable working-class life while fighting to contain his addictive and violent tendencies.

It’s a book about poverty and people on the margins, people who shun cultural norms and conventions while paradoxically dreaming of achieving the kinds of lives they claim to despise.

This book pulls no punches: it’s mean-spirited, misogynistic, homophobic (even thought the narrator occasionally partakes in homosexual liaisons), bleak, and cynical.

It works primarily as an unrelenting reminder that people like Dante exist.

Although it’s well written and filled with dark humor, it’s populated by unlikeable characters—and a repugnant narrator. But Bruno Dante is an interesting character. He knows his flaws, recognizes his bigotry, and fights to control his addictions as he struggles to become a better person. In the end, he fails, but Dante’s adventures in four other books by Fante occasionally offers hope that he can change.

The Handmaid’s Tale by Margaret Atwood (McClelland and Stewart, 1985)

As prescient now as it was when it was written during the Reagan revolution and the rise of people like Jerry Falwell and his so-called silent majority, Atwood’s harrowing dystopian novel imagines a world where Christian Theocracy has altered society, forcing women into subservient roles as second-class citizens who exist primarily to push out babies.

Whether you’re a man or a woman, a Christian or a Jew, a Muslim or a Buddhist or an atheist, The Handmaid’s Tale will disturb you. It will implant a creeping sense that the world Atwood imagines isn’t far-fetched. It can—and probably will—happen here.

By pulling the threads of norms and conventions already established in our world, Atwood warns of the logical conclusion of religion and nationalism when controlled by monsters on the extreme fringes of society.

Tropic of Cancer by Henry Miller (Obelisk Press, 1934)

It’s easy to hate this book: Miller is a cynical pervert who hates many kinds of people. It’s told in a stream of consciousness style with little attempt to forge a plot—or even tell a story. Writing in the first person present tense it at times reads as if it were cobbled from pages of a diary.

Miller meanders from story to fantasy to reminisce. He’s obsessed with sex and often thinks about fucking and imagines the cunts—a favorite word of his—of women he encounters. He’s a miserable bastard who criticizes Jews, homosexuals, Christians, and treats women as objects. It’s easy to dismiss Miller as a bigot, and this book as the product of a privileged white male running amok in an era when only privileged white males ran amok.

But to dismiss it as such would betray a superficial reading. Miller’s narrator is far more complex than his appearance leads you to believe. He absolutely makes appalling remarks about Jews and homosexuals and women—but he also makes appalling remarks about himself and all humans. He’s not bigotry personified. He’s misanthropy personified.

Mistaking his misanthropy for bigotry, however, might allow you to miss the bigger themes of Tropic of Cancer. The narrator loves the world. He’s obsessed with its natural beauty, it’s poetry, and everything wonderful and awe-inspiring in it. But the economic and the political strife of the first half of the twentieth century—the First World War, which consumed millions of lives and the depression that crippled the entire western world, eventually laying the foundation for European Fascism—scarred the psyches of everyone who lived in that period. It thrust the entire world into a state of PTSD, allowing the worst aspect of humans to emerge.

Rapid technological growth in conjunction with depression, war, and radical—and dark—political change plunged generations into despair, the same kind of despair Celine conveys in Journey to the End of the Night.

This is a psychological diagnosis at its core, one Nietzsche anticipated a generation earlier: when the old social order and morality gave way to the new, nihilism took hold. What’s the point of attributing value to humans if they’re just animals? This is the undercurrent of Miller’s deeply complex narrator. Although he is misanthropic and cynical, his observations and tastes betray a subtle, subconscious desire for a bright beautiful world where there’s little reason to distrust fellow humans.

Tropic of Cancer is a deeply complex novel. It requires close reading and learning to unpack the obscure stream of consciousness passages. Miller was a brilliant prose stylist who produced some of the most breathtaking prose in the first half of the twentieth century. He was also a brave writer: he was willing to alienate everyone, readers included, to illustrate a world devoid of morality, love of fellow humans, and order. And, to be honest, he was also an asshole.

The narrator is repugnant and offensive, which was part of the reason this novel was banned in America for years. Transgressive books are, their cores, offensive. This book certainly meets that condition. But it’s worth reading for the prose, to gain insight into the thinking of misanthropic pieces of shit, and to base this insight on experience instead of presuppositions—and, oh, the prose.

Last Exit to Brooklyn by Hubert Selby, Jr.
(Grove Press, 1964)

Few writers excel at producing bleak material. Hubert Selby, Jr., is one of them. In his dirge to life on the fringes, Last Exit to Brooklyn is likely to leave an impression on everyone who reads it.

Populated by transvestites, the addicted, psychopaths, and the downtrodden, Selby’s classic examines life on the margins. While not a novel in the traditional sense, Last Exit is a collection of stories connected by themes and the city of Brooklyn.

This is a frank and honest portrayal of life on the margins. More importantly, it’s a depiction of the consequences of poverty in the richest nation on the planet. The material proved shocking to audiences in the early 60s. To people in the middle class, riding the high of the post-war, post-Eisenhower boom, such dregs of society serve no place in a civilized country.

But the characters Selby portrays—many of whom were based on people he knew—are not victims of their own excesses and poor choices. They’re victims of their social strata. Alcoholism and drug use, violent crime and depression and suicide are correlates of poverty. It’s easy to overlook the notion that these people developed in a social prison imposed on them by those with power or money. It’s much harder to recognize them as symptoms of a nihilistic nation obsessed with limiting the distribution of money and opportunity.

A brutal and unflinching book, Last Exit to Brooklyn is a must read, a harrowing tale of people left behind by a first world power.

The Sun Also Rises by Ernest Hemingway
(Scribner, 1926)

What? you might ask. You’re seriously including this book on a list of transgressive books? There’s nothing transgressive or controversial about it. Hemingway the writer is about as milquetoast as they come.

After nearly a century in the Western Canon, and diluted by thousands of imitators and works derived from Hemingway’s first published novel, The Sun Also Rises has lost its edge. Our culture is now far more violent, intoxicated, and promiscuous than the characters and events depicted in this novel. When taken together, these two elements have softened this novel’s blow.

But if you view it through the lens of America in the 1920s, you might understand the shock and controversy The Sun Also Rises elicited on its publication.

Women had won the vote less than a decade earlier, the nation was segregated, it was dominated by strict patriarchal, Christian tenets. Sex was something you performed out of sight, without discussing it. The prohibition was still in effect, puritans having won an amendment outlawing alcohol. In a polite society, men and women didn’t drink, have loose and reckless sex, or cavort without consideration for the good of society. Although these points don’t describe the real America, they do describe the ideal America, and people always emphasize the ideal while ignoring or overlooking the real.

Featuring promiscuous men and women who drank and bounced from partner to partner, women who ‘swore and behaved unladylike, like men,’ The Sun Also Rises was like a grenade tossed into the tent of polite society. It was a book by and for young people. The older generations hated it. Even Hemingway’s mother denounced it. In a letter to her son, she wrote

It is a doubtful honor to produce one of the filthiest books of the year …. What is the matter? Have you ceased to be interested in nobility, honor and fineness in life? …. Surely you have other words in your vocabulary than “damn” and “bitch”—Every page fills me with a sick loathing.

It was a rallying cry for a generation uprooted and traumatized by the most violent war the world had ever seen. Written in concise prose, subtle, and, at times, beautiful, The Sun Also Rises is a masterpiece of transgressive fiction. The decades may have eroded its controversy, but it still deserves a place on this list.

Invisible Man by Ralph Ellison
(Random House, 1952)

One of the great masterpieces and works of literary art of the American Empire, Ralph Ellison’s Invisible Man portrays life as an African American in the first half of the twentieth century.

Indebted to Dostoevsky’s Notes from Underground and Joyce’s Ulysses, Invisible Man is narrated by an unnamed African American who has escaped society to dwell in an underground room.

He tells of his life as an invisible man, a person neglected and dismissed, hated and scorned by a society dominated by white people who accept the fallacy of race and racial inferiority and superiority. This novel exposes hatred and bigotry and conveys it to audiences—some of whom are white—who can’t possibly encounter the kind of hatred and dismissal African-Americans experience on a minute-by-minute basis.

Told in a rich, beautiful voice—Ellison was one of the twentieth century’s great prose stylists—Invisible Man subjects its audience to brutal acts of violence, racism, and repression.

It’s a deeply humane novel published in the days of segregation and public lynchings. And it asks for one thing: that we acknowledge the existence of every human being, that we treat everyone, even those shunned or on the fringes, as we ourselves expect others to treat us.

Heliogabalus, or the Crowned Anarchist by Antonin Artaud
(Original Publisher unknown, written in 1933)

Antonin Artaud was a French actor and theoretician of theater. His influence on theater is still felt. In his time, and in the generations to follow, he developed a rallying cry for avant-garde theatre. As a result, he forever altered the course of even mainstream theater.

For a time, he was a member of the surrealists, but he had a falling out with several members, including Andre Breton, the founder and totalitarian of the group. Although his writings bear certain hallmarks of surrealism, his style and voice are uniquely his own. He was such a singular and original writer, in fact, that no analogue exists. You simply can’t compare him or his writings to any other writer, before or since.

Artaud suffered from mental illness. His writings largely constituted a transcript of his rapidly deteriorating mind. In them, you’ll find beauty and madness as he focuses on his mental struggles and unknowingly disconnects from the human world.

Heliogabalus, or the Crowned Anarchist is a work of unrelenting madness. Ostensibly a biography of an obscure Roman Emperor, Heliogabalus dwells on esoteric—probably fictionalized—religious rituals. It also makes outlandish claims and assertions for which no evidence exists. Historians routinely dismiss this book as ahistorical gibberish—and it is. But it’s beautiful and insane gibberish.

It’s a descent into madness and Artaud’s deteriorating brain is our guide.
Nietzsche argued that philosophy books conveyed information about, and biases held by, the people writing them. Instead of exploring objective truth, Nietzsche claimed, a work of philosophy did little more than to reveal the personality of the philosopher. I accept his argument, and it’s no clearer and easy to infer than by reading Heliogabalus, or the Crowned Anarchist. This isn’t a book about a spoiled Emperor. It’s about a brilliant writer unknowingly producing a transcript of his decaying mind.

Finnegans Wake by James Joyce
(Faber and Faber, 1939)

Written over a 17 year period while Joyce battled problems with his eyesight, Finnegans Wake is unlike any book ever written. It’s big, dense, and written in an idioglossia composed of as many as 70 actual languages,

Finnegans Wake is at times an impenetrable novel. Experts have analyzed it and interpreted it for decades. Although they seem to broadly agree on some characters and the overarching ‘plot,’ if that word even applies here, much of this book remains enigmatic.

While Ulysses occurred in a single day, Joyce intended his followup to occur in a single night. With language both spellbinding and infuriating, it’s a difficult novel to approach. Contrary to some claims, however, it isn’t unreadable, but it does take effort. Such effort can yield breathtaking and poetic passages, such as this

Sniffer of carrion, premature gravedigger, seeker of the nest of evil in the bosom of a good word, you, who sleep at our vigil and fast for our feast, you with your dislocated reason, have cutely foretold, a jophet in your own absence, by blind poring upon your many scalds and burns and blisters, impetiginous sore and pustules, by the auspices of that raven cloud, your shade, and by the auguries of rooks in parlament, death with every disaster, the dynamatisation of colleagues, the reducing of records to ashes, the levelling of all customs by blazes, the return of a lot of sweetempered gunpowdered didst unto dudst but it never stphruck your mudhead’s obtundity (O hell, here comes our funeral! O pest, I’ll miss the post!) that the more carrots you chop, the more turnips you slit, the more murphies you peel, the more onions you cry over, the more bullbeef you butch, the more mutton you crackerhack, the more potherbs you pound, the fiercer the fire and the longer your spoon and the harder you gruel with more grease to your elbow the merrier fumes your new Irish stew.

I’ve read the book twice and I don’t pretend to understand it. From my personal experience, however, I find it hilarious. In fact, when people ask me for the title of the funniest book I’ve ever read, I always cite Finnegans Wake.

The cobbled language produces portmanteaux and puns that strike you as funny on a visceral level. You might not be able to articulate why a phrase or passage is funny, but many passages throughout this book will have you laughing out loud.

So why’s this, of all books, on the list? Isn’t Ulysses more explicitly transgressive? In its content, it probably is; however, with Finnegans Wake Joyce transgressed living natural human language and the appearances and mechanics of storytelling. Under those conditions, this book remains so transgressive that, eight decades later, no one fully understands it.

Faggots by Larry Kramer
(Random House, 1978)

Fred Lemish is a gay man looking for love in a subculture shunned and condemned by society. In a time when gay men still lived on the fringes, forced to hide their sexuality for fear of persecution—or worse—many men chose to forego relationships for anonymous sex with fleeting partners.

Published in 1978, before the AIDS epidemic ravaged many gay communities, Faggots is a stark and brutally honest portrayal of the underbelly of the gay community in New York. It’s filled with hedonism, drug use and abuse, violence, and graphic sex scenes.

Some scenes in this book might repulse those who are in uninitiated in the variety of sexual fetishes and desires. It’s a no-holds-barred look at sex and drug use on the fringe of an already fringe group.

At its core, however, Faggots is a moving and human book about love—wanting to be in love and wanting to feel that love reciprocated. It’s also an indictment of a society that prides itself on inclusiveness, morality, and empathy while condemning anyone who deviates from the norm.

Faggots is brutal in its unflinching depiction of life on the edges of a so-called free society. It’s also a landmark book, perhaps more responsible for ushering in the era of gay literature than any other book. It’s as important a cultural artifact as Ralph Ellison’s Invisible Man. In a sense, both books depict human beings rendered invisible by a society claiming to accept everyone.

A Scanner Darkly by Philip K. Dick
(Doubleday, 1977)

People who are aware of Philip K. Dick seem to fall into two camps: those who know him only as a science fiction writer whose works have been adapted to films and television and those who know him as a drug-eating philosophical mystic who experienced either a numinous moment or a psychotic break.

For those in the first camp, A Scanner Darkly‘s depiction of the dark side of drug use might subvert, or even pervert, their understanding of who Dick was.

This is a deceptively complex novel. It deals with notions of personality, the impermanent nature of subjective reality, and the toll drugs take on the human psyche.

PKD was active in the facet of the 60s subculture that freely used drugs and “expanded consciousness.” Toward the end of his life, he discussed drugs with openness and honesty. He touched on his use in frank terms and lamented the many young people he knew who went insane or died as a result of their drug use.

“Everything in A Scanner Darkly I actually saw,” Dick once said. It’s a stark and dark appraisal of the idealism of the 60s that fueled the drug culture. The paranoia, the psychosis, the breaks from conventional society, and suicide depicted in this book are often the consequences lighter fare, such as Fear and Loathing in Las Vegas or Cheech and Chong comedies dismiss or overlook.

On writing this, he referred to it as his “anti-dope” book. A Scanner Darkly emphasizes the terror and self-loathing concomitant to excessive drug use. It’s the flip side of stoner comedies. Although it contains science fiction elements and is a sort of alternate history, at its core it’s a book about the effects drugs had on an entire generation.

Arguably one of Dick’s best novels, A Scanner Darkly is an interesting entry into the subset of transgressive fiction. It’s a novel that illustrates the consequences of dealing with social norms imposed on you by escaping into your head with the help of powerful, and sometimes fatal, narcotics.

How to Talk Dirty and Influence People by Lenny Bruce
(Playboy Publishing, 1965)

Perhaps the most important comedian of the twentieth century, Lenny Bruce introduced satire and social commentary to mainstream comedy. His career started as any other in the 1950s: telling jokes wherever he could—bars, strip clubs, fledgling nightclubs. His career started with a whimper as he told jokes typical of the time. But when he found his voice, he forever changed the face of comedy—and became a target for federal and local law enforcement and puritanical groups intent on preserving the bland discourse of totalitarian 50s America.

No topic was off the table or taboo for Bruce. He discussed sex and race relations, war, American imperialism, and the two-faced bigotry of the American Empire. In the age of McCarthyism and fanatical cultural authoritarianism, Lenny Bruce peppered his onstage banter with the unthinkable: mature content and swear words.

He quickly developed a reputation as a man willing to speak his mind, willing to engage in frank discourse on sex and politics, and to use words such as fuck, motherfucker, cocksucker freely. Freedom of speech wasn’t absolute in the 1950s and early 60s. The media acted as a mouthpiece for official government policy, the Red Scare ruined the careers of anyone suspected of communist sympathies, books were frequently banned, obscenity in any form was outlawed.

But Bruce didn’t care. He recognized the hypocrisy of the government, as well as the inherent meaninglessness of words. He was arrested numerous times for the content of his performances and became notorious as an outlaw and a threat to American decency. But his troubles with the law only strengthened his resolve. In the land of the free, he seemed to think, people have the right to freely discuss what they want, to use whichever words they choose to use. Suppressing words, he argued, is how they derived their power.

Well, I was just trying to make a point, and that is that it’s the suppression of the word that gives it the power, the violence, the viciousness.

As his legal troubles mounted, his mental illness deteriorated. He escaped the pressure applied by the government by shooting morphine, which ultimately killed him.

His performances were raw and honest, a slap in the face of Americans who insisted on phony decency. He was harassed, arrested, tormented. And his performances changed the face of American comedy and helped to shatter obscenity laws in this country.

He was a true transgressive, and his memoir encapsulates his spirit, his humor, and his foul mouth.

A Season in Hell by Arthur Rimbaud
(Originally self-published by Rimbaud in 1873)

The original enfant terrible of world literature, Arthur Rimbaud’s life is the stuff of legend. He revolutionized French literature while still a teenager, shattered the French insistence on traditional verse, introduced free verse to the nation, wrote revolutionary prose poems, and quit writing altogether—at the age of 21. He spent the remainder of his life running guns and seeking his fortune in Africa, forever turning his back on his youthful, revolutionary spirit.

Perhaps his greatest work, A Season in Hell (Une Saison en Enfer) reads as equal parts experimental fiction and poetic and symbolic autobiography. His love affair with the poet Paul Verlaine, often abusive, ended when Verlaine shot Rimbaud in the wrist and was eventually sent to prison for the “sin” of passive homosexuality.

A Season in Hell is Rimbaud’s attempt to make sense of the madness, the shooting, and his own life, poetry, predilections, and madness. Considered a masterpiece of world poetry, and perhaps the greatest prose poem ever written, A Season in Hell might be the product of an existential crisis triggered by his shooting.

Composed of nine parts, each examining a facet of his history, his life, his personality, his relationships, and his art, this prose poem is unlike anything produced before or since. Rimbaud was an idealist: he believed poetry could change him—and the world. After the shooting, when the starkness of life settled over him and shattered his idealism, his optimism waned. Shortly after composing A Season in Hell, he turned his back on literature.

Les Chants de Maldoror by Comte de Lautréamont (Isidore Ducasse)
(Originally published by Gustave Balitout, Questroy et Cie., 1868-69)

Few works in world history are as shocking and disturbing, hallucinogenic and phantasmagoric, disorienting and brilliant as Les Chants de Maldoror. Divided into six parts, or cantos, Maldoror is a prose poem of epic length, a work with no antecedents. It ostensibly follows an enigmatic man named Maldoror, a disturbed human who shuns all human morality and norms.

I am filthy. I am riddled with lice. Hogs, when they look at me, vomit. My skin is encrusted with the scabs and scales of leprosy, and covered with yellow pus.[…] A family of toads has taken up residence in my left armpit and, when one of them moves, it tickles. Mind one of them does not escape and come and scratch the inside of your ear with its mouth; for it would then be able to enter your brain. In my right armpit there is a chameleon which is perpetually chasing them, to avoid starving to death: everyone must live.[…] My anus has been penetrated by a crab; encouraged by my sluggishness, he guards the entrance with his pincers, and causes me a lot of pain.

Lautréamont predated the surrealists by a generation yet his works are filled with surreal imagery, scenes, creatures, and conversations. He eschews norms and traditions in ways later avant-garde groups would struggle to top. In fact, Lautréamont was critical to the development of surrealism. Andre Breton, the founder of the movement, cited a Lautréamont line as the impetus for his development of surrealism:

As beautiful as the chance encounter of a sewing machine and an umbrella on an operating table.

The surrealist writer Louis Aragon even modeled his “anti-novel” Paris Peasant on Les Chants de Maldoror.

If poets such as Baudelaire and Rimbaud fired mortars at convention, Comte de Lautréamont launched thermonuclear weapons. A century and a half later, Maldoror doesn’t fail to shock and disturb. It’s a masterpiece of madness, insanity, and, strangely, beauty.

Slaughterhouse-Five, or the Children’s Crusade by Kurt Vonnegut
(Delacorte, 1969)

Written during the height of the Vietnam War, Kurt Vonnegut’s polemic remains as important now as it did on its release. A biting satirist and cynic with science fiction sensibilities, Vonnegut possessed a sociologist’s eye and a talent for distilling the human condition to its profound absurdity.

In his best known, and probably greatest novel, Vonnegut wrote perhaps the definitive anti-war novel when he set Slaughterhouse-Five to paper. Experimental at its core, the novel only loosely follows traditional structure while telling a non-linear story. It follows the life of Billy Pilgrim, a young soldier in World War II who survived the deadly bombing of Dresden. When he’s abducted by aliens, he becomes unstuck in time and experiences his life—past, present, and future—almost simultaneously. Time for Billy has become non-linear: he experiences his marriage, his time in the war, and even his death over and over again.

Vonnegut was a moralist who abhorred the horrors of war and expressed cynicism and skepticism with regards to capitalism and nationalism—both root causes of war. Having himself survived the destruction of Dresden, which killed over 100,000 civilians, Vonnegut spent the rest of his life traumatized by that event.

Slaughterhouse-Five is an unequivocal condemnation of war. It’s also an expression of the human costs of violent conflict. Although until recently the trauma of war wasn’t treated as a mental illness. Now we know it for what it is: Post Traumatic Stress Disorder (PTSD). In telling his story nonlinearly, it’s possible that Vonnegut set out to convey the experience of PTSD to those fortunate enough to have never experienced it. The non-linear way the story is told might reflect the confusion of time and experience those suffering from PTSD experience on a daily basis.

A Clockwork Orange by Anthony Burgess
(William Heinemann, 1962)

Later in life, writer Anthony Burgess didn’t think fondly of this novel. He dreaded the thought of being remembered for A Clockwork Orange over his other novels. To a degree, Stanley Kubrick’s adaptation spoiled the novel for Burgess. The film also filled him with terror. By omitting the final chapter that appeared in the British edition of the novel, Kubrick’s film ended on a darker note, muddling the themes and intention of the novel. This was a book and film, Burgess feared, that could inspire violence.

Although violence is inextricably linked to the novel and the film, it’s not the central theme of the book. A Clockwork Orange is a condemnation of totalitarianism and the authoritarian tendency to enforce conformity at all costs, even if it means rewiring a citizen’s brain. This is an anti-authoritarian novel, a criticism of the government’s role in dictating the behavior of its citizens, especially the youth. In focusing on the behavior of unruly, even violent children, the state could establish precedents that, when normalized, could expand to all citizens.

A Clockwork Orange is a masterpiece. If you excluded the original final chapter, it’s nearly perfectly structured and paced. The prose is breathtaking and the youthful slang Burgess invented for his young characters—the so-called Nadsat—introduces us to a world both familiar and alien.

(As an aside, it’s interesting to note that Nadsat is rooted in the Russian Language. Since this novel was written and released during the early decades of the Cold War, I’ve long wondered if Nadsat itself is an allusion to the conflict between the Soviet Union and the West. Since the Soviet language has successfully penetrated the youth cultures in this novel, I’ve long wondered if it’s an expression of doubt that the West can win. All wars bleed into cultures. Successfully penetrating a culture could give the opposing side an edge. Since the Soviets in this world successfully penetrated British culture, perhaps the government’s insistence on re-programming its citizens is an attempt to crush Soviet influence. You should note that this is my interpretation, so take it lightly.)

Naked Lunch by William S. Burroughs
(Olympia Press, Grove Press, 1959)

One of the most notorious books of the twentieth century, Naked Lunch is a world unto itself. Cobbled together from notes, stories, and gags Burroughs wrote over the years, often while under the influence of heroin, Naked Lunch is a novel in name only. It doesn’t follow a story, it’s not guided by plot, characters appear and disappear, sometimes they emerge but they never follow the hero’s journey or experience an arc.

This is less of a book and more of an experience. It’s a shocking, appalling, surreal trip into the mindset of drug psychosis. Filled with murder and explicit homosexual acts, obscene language and situations, pointed criticisms of America, the West, and capitalism, the book was an assault on everything the Western world held as decent and sacred.

Burroughs, a homosexual junky who accidentally killed his wife years earlier, did nothing to conceal his past or predilections. In condemning the novel, most people were also quick to condemn the author himself.

The book was so shocking that it was frequently banned. The ban was finally lifted as the result of a landmark trial, one that established absolute freedom of speech and of the press. As transgressive as this book remains, it’s important for another reason: it helped to break the United States’ habit of determining which material was or was not acceptable for public consumption.

Juliette by Marquis de Sade
(Published 1797-1801)

No list of transgressive books could overlook or ignore Marquis de Sade. Two centuries later, his books still shock and offend. They’re even still banned in some countries. To even the most jaded modern readers, Sade’s works contain scenes or ideas so brutal that they’ll appall you, make you flinch, and haunt you.

Although not his most notorious novel—that distinction belongs to 120 Days of Sodom—Juliette is the distillation of every major theme, philosophical argument, and grotesquery Sade conceived in his life and letters. This nearly 1,300 page tome—the paperback edition is roughly the size of a small cinderblock—possess the power to interest and intrigue, provoke thought and induce repulsion.

It follows the story of a poor woman, Juliette, who climbs the social ladder by participating in and orchestrating appalling acts of sex and violence solely to entertain bored, depraved aristocrats and clergymen.

Well formulated and convincing philosophical dialogues complement the sickness and depravity. On one hand, this book—like all of Sade’s works—is a philosophical dialectic; on the other hand, it’s an exploration, even a celebration, of human beings most basest instincts and desires.

It’s a stunning, difficult, disgusting, mind-opening, and occasionally beautiful and empathetic book. It’s a masterpiece of world literature and the keystone to the most singular oeuvre in the history of the written word. This book, and Marquis de Sade, will forever remain transgression personified.

Do you agree with the books on this list? Disagree? Feel free to comment. Let me know which transgressive books you’ve felt drawn to over the years.

 Daulton Dickey is a novelist, poet, and content creator currently living in Indiana. He’s the author of A Peculiar Arrangement of Atoms: Stories, Still Life with Chattering Teeth and People-Shaped Things, and other stories, Elegiac Machinations: an experimental novella, and Bastard Virtues, a novel. Rooster Republic Press will publish his latest novel, Flesh Made World, later this year. Contact him at daultondickey[at]yahoo[dot]com.