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Controversial books challenge the mind and the societies they critique. They are not the types of literature with which you always agree, but they do provoke conversation and challenge understandings of the world around you. Not every controversial book on the list of 18 below should be taught in a classroom. Some suffer from serious quality deficiencies while others are only appropriate to specific age groups. It is not so much a matter of censorship as whether the age group targeted is ready to understand all of the themes and relate to them. With that said, let’s get started!

1. Memoirs of a Woman of Pleasure

What is a guy to do when he is stuck in debtors prison? Write the world’s first erotic novel, of course! That is what happened with John Cleland in the UK. His book Memoirs of a Woman of Pleasure, more popularly known as Fanny Hill, is about a young girl with a very limited education living near Liverpool.

Just after her 16th birthday, her parents die leaving her to find her way in the world before she’s ready. Her first experience with this comes when she crosses paths with Mrs. Brown, a woman she naïvely believes to be a wealthy lady and nothing more. Mrs. Brown is actually a pimp and desires Fanny to work under her. Fanny has her first taste of sex for pleasure with a woman. Controversial enough for the time, but things get considerably more graphic from there. How graphic? You’ll have to read it for yourself.

As a result it has been one of the most banned books of all time since its initial publication in 1748.

2. The Communist Manifesto

The Communist Manifesto by Karl Marx was written in late 1847 and first published the following February. The first translation turned up 40 years later in 1888 consisting of the preamble, followed by four main sections. The first section has to do with the bourgeois and proletarians. The second section has to do with proletarians and communists. The third section covers socialist and communist literature. And the fourth section deals with the position of the communists in relation to the various existing opposition parties. In the United States, The Communist Manifesto has been one of the most controversial books because it runs contrary to the founding principles of the United States. It was the book at the heart of the 40-year Cold War that ended with the destruction of the Berlin Wall. The Communist philosophy — that the state is greater than the individual — originated here.

3. The Adventures of Huckleberry Finn

The Adventures of Huckleberry Finn by Mark Twain is not only one of the most controversial books ever, but it is also one of the most biting satires. It was preceded by The Adventures of Tom Sawyer and Tom Sawyer Abroad followed it. The reason Huckleberry Finn is so controversial has to do largely with the use of language. The “N-Word” is a regular piece of verbiage from the titular character, who is right at the intersection of racism and sympathy for the plight of slaves. His relationship with the slave Jim colors his understanding of right and wrong and creates conflict between what he’s been taught and what he knows to be true. These days Huck Finn is a book at the heart of the trigger warning debate, and there is something offensive for everyone. It has been adapted for film and television numerous times, but usually in a considerably watered-down version.

4. On the Origin of Species

On the Origin of Species by Charles Darwin was first written and published in 1859. It is a work of science that serves as the foundation of what is today known as evolutionary biology. The book introduced the scientific theory that population evolves over the course of several generations and through the process of natural selection. While many may struggle today to see the controversial nature of the book, it is actually not difficult to figure out once you see how Darwin picks at the core of most of the world’s religions. Darwin’s findings run counter, in particular, to what Christian churches commonly say about the creation and development of the universe. Since Christianity was the prevailing religion of the day and remains so from a population standpoint, the book remains a lightning rod almost 200 years later.

5. The Kindly Ones

The Kindly Ones by author Jonathan Littell was originally written in the French language and translated by Charlotte Mandell. It was published first in 2006 and translated into English in 2009. The book is an autobiographical novel dealing with the life of a former officer in the SS. He shares his experiences as part of the Third Reich security force. The book is divided into seven chapters, each named for a Baroque dance. The main character does not feel the need to repent for his crimes, “believing that it was my duty and that it had to be done, disagreeable or unpleasant as it may have been.” He has an incestuous relationship with his sister. He “converts” to homosexuality because he does not want to pervert the relationship he shared with her by sleeping with another woman. Given these small facts from the 902 pages of provocative prose, it is easy to see why the book touches a nerve.

6. The Catcher in the Rye

J.D. Salinger’s controversial 1951 novel takes place during a three-day time period in December 1949. Its main character, Holden Caulfield, is a 16-year-old New York City boy who flunked out of a prestigious private school. He shares his story from a tuberculosis rest home a year after the events occur. The primary source of anger directed at the book comes from the use of language. Holden is often vulgar, and the events of the book feature many sexual references, blasphemy, and the undermining of family values and moral codes. It also encourages rebellion, promotes drinking, promiscuity, smoking, and lying. As a result, religious leaders and parents have taken exception to its conclusion in literature curriculum. Even so, the book is largely seen as a masterpiece. It was included by Time magazine in a 2005 list of the 100 best English-language novels written since 1923. Modern Library and its readers also named it as one of the 100 best English-language novels of the 20th century.

7. Lady Chatterley’s Lover

Lady Chatterley’s Lover, the controversial DH Lawrence novel from 1928, was at the heart of a dramatic watershed obscenity trial in the UK in 1960. Controversy has followed the book, and it is not difficult to see why considering its use of language and sexual promiscuity. The book deals with matters of infidelity, sexual awakening, and sexual experimentation. It follows the trials and tribulations of one Lady Chatterley, whose husband is injured in the Great War. Paralyzed from the waist down, Clifford Chatterley becomes neglectful of his wife as he spirals into depression. She finds a cure for her sexual frustrations with a gamekeeper. The novel stakes the claim that fulfillment must be a blend of mind and body; that happiness cannot come unless physical satisfaction is present. Not exactly the type of book parents want to see turn up on a semester reading list!

8. The Perks of Being a Wallflower

The Perks of Being a Wallflower is not exactly the type of book to make parents comfortable either. It centers on Charlie, a repressed young man who is coming to terms with his place in the world and his guilt over the death of his Aunt Helen, who died in a car accident on the way to buy him a birthday present. Charlie is haunted by the memories of that as well as something more sinister involving his late aunt. While in high school, he befriends Patrick and Sam. He develops a crush on Sam and a strong friendship with Patrick, a homosexual young man who has a behind closed doors relationship with a closeted football player. The novel is told through a series of letters and deals with many controversial subjects, such as teen sexuality and molestation as well as homophobia.

9. The Satanic Verses

The Satanic Verses is definitely a natural for this list because it has resulted in so many deaths over the years as well as a fatwa on the author, Salman Rushdie. The book is perceived to be blasphemous against Islam and for its perceived abuses of freedom of speech against the religion. Rushdie has been running for his life ever since but recently came out of hiding. There remains a $3.4 million bounty on his head. While no harm has come to him over the years, there have been a series of attacks resulting in the death of his Japanese translator, who was stabbed 11 times in July 1991. His Turkish translator was the intended target in the event that led to the Sivas massacre of 1993. Thirty-seven people died in that attack. Rushdie does not believe the novel could have even been published today. He’s probably right.

10. Uncle Tom’s Cabin

Uncle Tom’s Cabin has gone back-and-forth over the years as being controversial to southern whites or controversial to the black community. Today, calling someone an “Uncle Tom” is perceived as an insult against black people who try too hard to conform to white society. At the time of its publication, however, the controversy was much different in that it shed light on the cruelty of slavery and was a tremendous influence on the Civil War that broke out a few years later.

11. I Know Why the Caged Bird Sings

I Know Why the Caged Bird Sings is a controversial book of autobiographical fiction by author Maya Angelou. It is called autobiographical fiction because it is written in a style similar to a novel, but it details the events that happened to Angelou as she grew up in Stamps, Arkansas. The book is controversial because it deals graphically with racism, sexuality, and rape. As if rape was not controversial enough, the specific scene happens to an eight-year-old girl making the book incredibly uncomfortable for parents and students alike. It has been praised as a work of literature, but frequently banned in schools.

12. Lolita

Lolita by Vladimir Nabokov will live in controversy for as long as the world stands due to its graphic depictions of a relationship between an unreliable narrator protagonist – a middle-aged professor – and a 12-year-old girl named Dolores, whom the narrator calls “Lolita.” The novel deals with adult themes like pedophilia and murder. What makes the novel especially unsettling is the point of view. Since it is told through the perspective of the pedophile, it is tinged with sympathy for that perspective. As a result, Lolita is less a child victim of sexual abuse and more of a seducer. The book has been frequently banned and protested throughout its lifespan in America, especially where conservative attitudes prevailed during its 1955 unveiling.

13. The Bible

When you separate the Sunday school interpretations of the Bible from actual words on the page, it is easy to see why this book remains one of the most controversial of all time. In its purest form the Bible is one story after another featuring sexually explicit behaviors, genocide, and controversial views on social issues. In a straight-through reading of it, you will see an overarching theme that God loves his creation (i.e. mankind), but there are numerous stories of sin and what constitutes sin that will inevitably offend someone. For examples, women are often cast in subservient roles to men, homosexuality is condemned, violence against women and children is supported in the Old Testament by God himself, and rape is sometimes condoned — not by God granted, but by other characters in the narratives. The Bible is also controversial because it runs counter to much of what is taught in schools and modern society, yet it remains a code of beliefs for many Americans and people around the globe.

14. Tropic of Cancer

Originally published in 1934, Tropic of Cancer by Henry Miller is one of the most controversial novels of the 20th century because of its free portrayal of sexuality. It has at times been considered pornographic, though in 1964 the US Supreme Court nixed that idea. Most of the controversies have to do with the promiscuities that are graphically depicted throughout. It is an autobiographical novel. Set in France in the late 1920s and early 1930s, it tells of Miller’s struggles as a young writer. He often suffers from things like hunger, loneliness, and homelessness, as well as a troubled marriage. The book uses a variety of offensive language, such as the F-bomb and the C-word.

15. The Lord of the Flies

It is difficult not to classify William Golding’s book, The Lord of the Flies, an allegorical novel, with the most controversial books. Published in 1954, it is a stunning debut though it was not particularly successful at the time. During a wartime evacuation, a British plane crashes near an island in the Pacific Ocean region. Two boys, Ralph and Piggy, find their way to a group of survivors. While on the island the young people must learn to hunt and survive on their primal skills. The book is considered somewhat violent for the age group of the characters and the ages of the students likely to encounter it. It deals with controversial subjects like human nature and the welfare of the individual versus the welfare of the common good. The American Library Association has placed it on its list of the 100 most frequently challenged books of the 20th century.

16. The Chocolate War

Robert Cormier’s 1974 novel The Chocolate War is considered controversial because of the content and the age group it is written for. It is considered a young adult novel. However, it has a critical eye for religion, and it deals somewhat graphically with sexuality. It follows Jerry, who starts at an all-boys Catholic high school. He is depressed and feels largely alone due to his mother’s death and his father’s anguish. He starts playing football on the varsity team, and the rest of the novel takes a coming-of-age bent, which bumps up against some controversial subjects – namely sexuality and strong language as well as some graphic depictions of violence. Like the previous book on this list, the American Library Association has named it as one of the top 100 in its listing of banned and challenged books.

17. The Da Vinci Code

Dan Brown’s The Da Vinci Code may seem like a harmless adventure story, but anytime you start reimagining the role of one of history’s greatest figures while painting a long-heralded institution like the Catholic Church as a villain, you are bound to ruffle a few feathers. One of the most controversial aspects of the novel is in suggesting that Jesus Christ actually had a wife – something Scripture never discredits nor claims. Because so many people have close spiritual ties to Jesus and Christianity in general, the hypothesis presented by the book caused it to be a political hot potato, which it continues to be 13 years after its initial publication.

18. Fifty Shades of Grey

50 Shades of Grey is an erotic romance novel from 2011 that gets quite a bit of attention when it comes to controversy because a) it is poorly written, b) it presents a series of ludicrous character interactions, and a c) managed to somehow become a bestseller in spite of itself. The reality, of course, is the book’s steamy sadomasochistic sex scenes. The book’s female lead, Anastasia Steele, becomes enamored with her interview subject, 27-year-old Christian Grey. Six years separate them, but Grey has quite a bit more experience with life going into their relationship. He unlocks in her a desire to be dominated. The book is seen as counterproductive to feminism and an assault on quality literature.

So there you have it, readers. Now we are well aware of the subjective nature of a list such as this one. Therefore, we invite you to share your suggestions in the comments section below. Also, do you think these books are deserving of the reputation they have received? Sound off!