10 Shocking Novels More Scandalous Than 50 Shades Of Grey

50 Shades of Grey is notable as one of the most controversial and popular books of the modern day canon. Demonized by many for its poor writing, its obscene content, or any other number of problematic aspects, it is one of the most divisive, and best selling books out today.

While the merits of this trilogy are openly debated, there is no question that great art and obscenity have had a long and profound relationship across the span of history in the written word. These 10 books are considered some of the greatest books in history...and have had some of the most complicated, offensive, and scary histories in literary history. These books have enthralled, and excited for years and their value is not in dispute, if you need a fix of great literature...and a little bit of heat, here are ten books that are leagues more scandalous than the notorious 50 Shades series.

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10 Tropic of Cancer - Henry Miller

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Tropic of Cancer is a semi-autobiographical story of Henry Miller and his experiences with the Bohemian lifestyle in Paris. Using life as its subject to explore, Miller discusses with utter frankness and candor life, sex, depression, loneliness and the human condition.

This book is famous for its frank depiction of sexuality, Miller narrates in detail and with bluntness a number of sexual experiences he has while in Paris. As a result of the freedom with which Miller spoke of these subjects, the book was put to trial for obscenity. Ultimately it was deemed not to be obscene, and now stands as one of the greatest works of literature produced in the 20th century.

9 Portnoy's Complaint - Philip Roth

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Portnoy's Complaint is a single sustained monologue by main character Alexander Portnoy to his psychiatrist. Portnoy, a neurotic, sexually insecure American Jew discusses in intimate detail growing up in Jewish suburbia; his neuroses, his frustrations, his observations on others, and his past with women and himself.

Infamous for one explicit scene involving chopped liver, Portnoy's Complaint stands as one of the most famous books in Philip Roth's collection. While at times it can be over the top in its depiction of its main character, it's nevertheless frequently hilarious and contains just enough individual truth that it makes it worth turning the page. It, perhaps unsurprisingly, is banned for those reasons in a number of countries and was the focus of intense scrutiny elsewhere.

8 Howl and Other Poems - Allen Ginsberg

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Howl is a monument of the 50's beat generation. Starting with the famous opening "I saw the best minds of my generation destroyed by madness, Starving, Hysterical, Naked", Ginsberg lays bare the experience of being a bohemian in New York. Squalor, mental illness, illicit drugs and sex all lie in between the various things Ginsberg laments on.

While technically speaking a narrative poem, Howl and Other Poems stands as Ginsberg's grandest statement. An epic that intimately examines life in poverty, and suffering for one's art, its complex structure, intricate wordplay, and the live recordings of Ginsberg's performances continue to enthrall and mystify.

7 Lady Chatterley's Lover - D.H. Lawrence

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This book was the 50 Shades of its time. The story follows Connie Chatterley, a woman whose husband comes home from war,  paralyzed from the waist down and emotionally distant. It explores the need for physical love in an emotionally intimate relationship- Lady Chatterley finds this by having an affair with a working class gentleman.

This book was, in the 60s, notorious. Its open depiction of an intimate sexual affair raised controversy and notoriety across the board. A great number of people openly condemned it for this reason. Its expression of the crucial need for physical intimacy in romance continues to arouse the interest of the masses.

6 Lolita - Vladimir Nabokov

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A book more infamous for the sub-genres it has spawned than its actual content, Lolita by Vladimir Nabokov is the story of the complex, inappropriate sexual relationship between Humbert Humbert; a man in his late 30's and Dolores Haze, a 12 year old girl whom he refers to as "Lolita". Covering a period of years it follows their relationship in all its complexities.

Nabokov's most popular work by far, it was adapted into a film by Stanley Kubrick and is (for better or ill) an enduring cultural icon. Nabokov, though deeply fond of the book, expressed distaste for the lead character, who is by all accounts a monster, albeit one with a seductive voice and perspective.

Though controversial for its content and its lasting impact on pop culture, it is frequently ranked as one of the greatest books ever written and was ranked number 4 on the Modern Library's list of the greatest books of all time.

5 A Clockwork Orange - Anthony Burgess

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Alex DeLarge and his Droogs are up to no good. Set in a near future, A Clockwork Orange is the story of the forced reformation of juvenile delinquent and genuine psychopath Alex DeLarge. After getting caught for a particularly heinous crime, he is subjected to an experimental therapy the "Ludovico Technique", where he is conditioned to become violently ill in the presence of violence. After being released, the world takes it upon itself to get payback.

Another book adapted into a film by Stanley Kubrick, the author of this book used a clever disguise to mask the more disturbing parts of this book. Burgess invented a Russian/English slang "Nadsat" that the main characters speak in. This has the effect of distancing readers from the unspeakably cruel things the lead characters do; in some ways this is one of the most obscene books on this list, but you might not always be able to tell due to the thick use of slang.

4 120 Days of Sodom or the School of Licentiousness - The Marquis de Sade

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The Marquis de Sade is perhaps the single most infamous example of pure, unadulterated excess and scandalous expression in literary history. Noted for his libertine lifestyle, his excessive appetites and his unadulterated hatred for religion, he spent a number of years in prisons and asylums for his various books and opinions on virtue. The term "Sadism" comes from his title and infamy.

The 120 Days of Sodom was written during his imprisonment in the bastille, and stands as his most extreme work. Unfinished because of the prison's liberatio, the work represents his controversial ideas taken to their absurd conclusion. Featuring four libertine men of utter moral bankruptcy, they capture eighteen young women and men and expose them to various obscene, utterly shocking acts.

This book does have artistic merit, but it is an extreme expression of the darkest impulses of humanity. The book itself is less well known than the Pier Pasolini adaptation it spawned, "Salo". Although the movie Salo rarely goes as far as its literary counterpart, it is often seen as one of the most extreme films ever made - it stands as a stark testament to the corrupting influence of power. The image above is one of the few SFW stills from the movie.

3 Venus in Furs - Leopold von Sacher-Masoch

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De Sade is responsible for the culture of Sadism, and von Sacher-Masoch is responsible for Masochism. Venus in Furs represents his most famous work.

A semi-fictional tale, this book is the story of a man who is enamored with a woman and offers to be her slave - think 50 shades in reverse. In opposition to the more common trope of the trope of a woman submissive to a powerful man, the main character willingly gives himself in suprasensual slavery to a woman.

In many ways this book represents the antithesis to the Marquis De Sade, and in some ways, Sacher Masoch is a perfect inversion of Christian Grey, using wealth and influence to be dominated instead of the reverse

2 Gravity's Rainbow - Thomas Pynchon

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Gravity's Rainbow is Thomas Pynchon's magnum opus. Widely known but not commonly read, it was nominated for the Pulitzer Prize in fiction in 1974 by the three member committee, only to be overturned by the eleven member board for being "Turgid, Unreadable, Overwritten, and Obscene".

Gravity's Rainbow follows the adventures of Tyrone Slothrop through war torn Britain, Germany, and the Zone. There are over 400 characters, hundreds of esoteric topics of discussion, bizarre situations, bizarre characters, and a number of "obscene" activities sprinkled throughout. This dream-like and twisted narrative has confounded and amazed readers of all backgrounds and has been cited as one of the greatest Post-Modern novels ever written.

1 Ulysses - James Joyce

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Using Homer's Odyssey as its source, it follows the least eventful day in history, with the least interesting man. It explores in absurd detail, Dublin Ireland. Even more closely however, it examines the human mind via its narrative experimentation and Joyce's use of Stream-of-Consciousness. The sum of humanities urges and thoughts are contained in this dense novel, from the transcendent dreams of Irish nationalists, to sex, to scatalogical humor and beyond. It chronicles every activity humans do honestly.

This book's obscenity trials, and the fight to have it released in america are probably the most famous fight for art ever seen. It took 14 years for this book to reach American shores legally, and ever since has been regarded as either a totally incoherent chaotic mess, or the single most monumental work of genius ever put to paper (Or both).

Ranked number 1 on Modern Library's list of the greatest books of all time. Ulysses is a monolith to the written word, life, the universe, and everything.

Sources: Modern Library, imdb, Pynchon Pomona, ALA

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