10 Books That Pushed the Edges of Art and Free Speech (1955 to 2005)


All the novels on this list, to some degree, were received by a shocked and sometimes outraged audience. Some pushed sexual boundaries and taboos, others offended societal and religious values, others offended basic human decency, and some even stirred up controversy outside of the pages themselves. A lot of them were banned at one point or another. Regardless of theme, plot, or technique, every novel on this book opened readers’ minds to things they’d never allowed themselves to imagine before (or at least admit to). They all have their own unique amazing crazy voice that reverberates, resounds, and echoes with ownership and authenticity.

These books pushed the edges of art and free speech. Approximately half of these novels were based, at least in part, on the authors’ lives, and these stories that roar like lions were how the writers pushed through their past. Shaped it. Gave it a life of its own that had to be told, if only because some of these things really happened. They really did. Or almost did. Or came really close to happening. Or could happen. Or are about to. Or are about to again.

And all things that happen should be told…because they are a part of all our stories, collected and collectively. Even if they are ugly and depraved. Even if it is hard to look.

Author’s note: In my opinion these are the ten absolute best written with a voice full of wanderlust that reverberates with talent, hard work and a screaming agony that takes your breath away.

10. Naked Lunch, 1959 (William S Burroughs)

Naked Lunch

First sentence:

I can feel the heat closing in, feel them out there making their moves setting up their devil doll stool pigeons, crooning over my spoon and dropper I throw away at Washington Square Station, vault a turnstile and two flights down the stairs, catch up uptown A train.

Naked Lunch is a about a junkie’s descent into depravity and madness, against the backdrop of a dystopian future. It is based on Burroughs’s real-life demons and drug addictions. It is wildly obscene and incoherent. It rambles into nightmarish descriptions of bug-people, technology replacing humanity, secret organizations, and chaos running amok. It is absolutely filled to the brim with drugs, sex, violence, and insanity. It is an understatement to say that the narrator is unreliable; the reader is never really sure what the hell exactly is going on or what to really believe. The ending simply dissolves into nothing, as if in the middle of the sentence, without any explanation or resolution.

The novel caused an unbelievable uproar upon publication. It was called many names: un-American, disgusting, offensive, filth, rotten, depraved, unethical, and perverse. It was first published in France in 1959 and then in America in 1962, only after Henry Miller’s Tropic of Cancer was cleared of obscenity charges in the same year. However, the novel was eventually charged with obscenity in Boston in 1965.

The ensuing obscenity trial in Boson is considered the last significant obscenity trial in American literature. It is interesting to note that a lot of the books on this list were only banned or deemed controversial in the United States (The Land of the Free). Writers such as Allen Ginsberg and Norman Mailer came out of the woodwork to support Burroughs and defend the novel, but the court still ruled the novel obscene.

It wasn’t until 1966 that the Massachusetts Supreme Judicial Court ruled in favor of the defense, deeming that the book did indeed have social value. Although one of the two dissenting Justices was, nevertheless, moved to put on record that the book was a “revolting miasma of unrelieved perversion and disease…It is…literary sewage.”

This ruling was a huge victory for defenders of the First Amendment, specifically writers and artists. It paved the way for many writers, musicians, and filmmakers of today, and this is the only reason I included this book on this list. This is the only book I included not based on its merit or writing quality. It just had to be on this list because without it some of the other books on this list may have never been accepted or published.

9. A Million Little Pieces, 2003 [Published as a Memoir] (James Frey)


First sentence:

I wake to the drone of an airplane engine and the feeling of something warm dripping down my chin.

This memoir opens with Frey waking up on an airplane so screwed-up from alcohol and crack and everything else that he doesn’t know where he is, or how he got on the plane, or where he’s even going. He goes to a rehab clinic and starts losing his mind without drugs or alcohol. He gets really really angry. Like absolutely unbelievably angry. He fights withdrawal. He fights every single person and situation he encounters. He fights his past. He fights the rage itself, knowing that he has zero chance of ever getting sober. This is what the book is about.

In 2005, Pieces was selected for Oprah’s book of the month club, and Frey appeared on her show to promote the book and discuss his memories and experiences. Soon after that appearance, The Smoking Gun released a report that exposed Frey as a liar. It revealed that Frey had highly elaborated, and in certain parts of the book blatantly lied about his experiences.

In the book, he claimed that he had caused the death of two of his female friends in a car accident. He claimed that he had been in jail for three months. He describes, in agonizing detail, several root canals he received at the rehab clinic, without any anesthetic or Novocain. But in reality, none of those ever really happened.

This stirred up a huge bed of controversy which led Frey to appear on “Oprah” once again in 2006, where she rebuked him. “I feel duped,” Ms. Winfrey told Mr. Frey, “But more importantly, I feel that you betrayed millions of readers.” He admitted to making up and exaggerating certain episodes in the book, and apologized.

The media uproar became so loud and opinionated that eventually Doubleday offered refunds to anyone who felt they had purchased the book under false pretenses. You had to mail them a copy of pg.128 or some other weird cryptic number. To this day, the book is still labeled as a memoir, but the majority of readers, in the know, take this with a grain of salt.

This is a great book; it’s just annoying that throughout the whole book Frey portrays himself as a bad-ass anti-hero renegade outlaw, but in real life Oprah almost brought the man to tears. He also looks like a teddy bear in his mugshot.

8. The Heart is Deceitful Above All Things, 2001 (Laura Albert/ JT Leroy)


First sentence:

His long white buck teeth hang out from a smile, like a wolf dog.

This is a collection of intertwined stories dealing with child abuse, drug abuse, transvestism, vagrancy, and prostitution. These stories are all based on Leroy’s own experiences as a child; his back-story was one of abuse, prostitution, drug addiction, and vagrancy in California. “According to the official story, available in dozens of interviews Leroy has conducted almost entirely by phone or email, Leroy was saved from his street life at the age of 13 or 14 by psychologist Dr. Terrence Owens.” The stories are narrated by Jeremiah, who at age four is taken from his foster parents by his insane drug/abused-addicted, birth mother, Sarah, who bursts with simultaneous urges to love her son and bring him down into her depraved world, so she’s not so alone. Jeremiah idolizes Sarah, and in most parts of the book willingly follows her to the lowest ends of the world (even when she acts like she doesn’t want him), so he can be like her….so he can be close to her. What follows is a disturbing odyssey of repeated physical, and psychological abuse, domination, abandonment, and drug abuse. The abuse in the stories is so horrible and pervasive that it’s hard to believe that Leroy ever escaped his own demons long enough to write them down and get them published.

Well the truth is that JT Leroy’s past was exaggerated…well actually that’s not exactly true. It turned out that Leroy didn’t even have a past because JT Leroy was not a real person.

In 2006, the New York Times revealed that JT Leroy was actually a woman named Laura Albert. Albert had fooled everyone. She had a friend of hers pose as Leroy at book readings, the advance for her first novel, Sarah was paid to her sister, and further payments were forwarded to a Nevada corporation, Underdogs Inc, whose president turned out to be Laura Albert’s mother.

Some people were upset. Others defended her art, claiming that it didn’t matter who supposedly wrote it…that authors had the right to remain anonymous, if they so desired.

Albert herself said, “For me it was created the way an oyster creates a pearl: out of irritation and suffering. It was an attempt to try to heal something. And it actually worked, and it did so for a lot of other people. The amazing thing is, now I can be available to people. It’s OK with me if someone doesn’t like my writing. But they shouldn’t try to tell me how I’m obliged to present my work.”

Either way you look at it, Heart remains a powerful, tour-de-force that dives into a dark underworld that the majority of us like to pretend doesn’t exist.

But it does exist. It really does.

7. We Need to Talk about Kevin, 2003 ( Lionel Shriver)


First sentence:

Dear Franklin, I’m unsure why one trifling incident this afternoon has moved me to write to you.

This haunting book is about one of the most avoided, debated, and misunderstood topic of all time: school shootings. Eva, the shooter’s mother, narrates the book, and the first scene opens with her scraping red paint (thrown by angry townspeople) off of her house, after the tragedy. Her son Kevin has killed her husband and daughter, as well as ten people inside of his high school, with a crossbow. He is sent to jail, and his mother remains in the same house Kevin grew up in, in the same town that now threatens, ridicules and hates her. This book poses questions about who is really to blame for tragedy and why it happens in the first place. Kevin was raised in an opulent home and given everything he could ever want, but then so are many of the recent mass school-shooters in America. (Maybe that’s the problem)

The novel hinges on the classic nature/nurture debate. Kevin is portrayed as a selfish, evil sociopathic figure as early as day one, but the mother’s indifference toward him predates even his birth. She was a self-made millionaire businesswoman who was nudged into conception by her husband, and she questions whether this is in fact the major factor behind the shooting. She has never liked her son, which causes even more controversy (never has a mother in any work of art been so honest about her dislike towards her own offspring). Although she is still a good mother…she just has an aura of dislike that her intelligent know-it-all son can see every moment of every day. But did she dislike him because he was a monster or did he become a monster because she didn’t like him?

It also points fingers towards society and the-looking-at-a-car-accident-as-you-drive-by mentality of America. The endless media coverage and sensationalism of it all. Kevin repeatedly refers to an “audience.” The book also references other real-life school shootings many times throughout the novel. But ultimately the reader is never given a complete answer as to why.

At the end of the book when Eva, for the first time, asks her son, “Why?” he responds, “I used to think I knew. Now I’m not so sure.”

6. American Psycho, 1991 (Brett Easton Ellis)


First sentence:

Abandon all hope ye who enter here is scrawled in blood red lettering on the side of the Chemical Bank near the corner of Eleventh and First and is in print large enough to be seen from the backseat of the cab as it lurches forward in the traffic leaving Wall Street and just as Timothy Price notices the words a bus pulls up, the advertisement for Les Miserables on its side blocking his view, but Price who is with Pierce & Pierce and twenty-six doesn’t seem to care because he tells the driver he will give him five dollars to turn up the radio, “Be My Baby” on WYNN, and the driver, black, not American, does so.

Now this book is a whole other kind of monster. Ellis has said as much, describing how at some points the book felt like it was writing itself. It follows Patrick Bateman: a rich Wall Street yuppie who becomes more and more disgusted (and bored) with his ornamental meaningless life and friends, until he finally changes into a depraved monster…a sick sadistic serial killer. He begins murdering woman, homeless men, and people in his own social circle.

For anyone who thinks they have become desensitized to anything in this culture, or this century, I dare you to pick up this book. Actually I don’t. This book is potentially the only book on this list that might really actually go too far. The only book you could make an argument for really being “obscene” and taken off the shelves. Not because it doesn’t have anything to say but because it says too much. If you have seen the movie, this book is much much worse. But the talent of the writing is undeniable.

It received a huge resounding backlash from critics, publishers, and readers alike. Simon and Schuster abruptly canceled publication of the book after excerpts of the book leaked, causing public outrage, despite the fact they had already paid Ellis a hefty $300,000 advance. Ellis’s life was threatened on more than one occasion. He was called every kind of name in the book. People went absolutely crazy, although it still debuted on the best-seller list. This book pushes the First Amendment right against the freaking wall.

5. The Satanic Verses, 1988 (Salman Rushdie)

Salman Rushdie

First sentence:

“To be born again,” sang Gibree Farishta tumbling from the heavens, “first you have to die”

When this wonderful mystical novel was first published in 1988 all hell broke loose. Ayatollah Khomeini of Iran issued a fatwa ordering Muslims to kill Rushdie, which still exists to this day. Khomeini’s office had this to say: “Even if Salman Rushdie repents and becomes the most pious man of all time, it is incumbent on every Muslim to employ everything he has got, his life and wealth, to send him to Hell. If a non-Muslim becomes aware of Rushdie’s whereabouts and has the ability to execute him quicker than Muslims, it is incumbent on Muslims to pay a reward or a fee in return for this action.” Rushdie had to go into hiding for a decade, and I’m assuming the man still locks his doors at night and surrounds himself with security (I know I would). One Iranian foundation recently put a $2.8m bounty on the author’s life.

And this wasn’t all talk either. There was an actual real assassination attempt in London, in 1989, but the bomb exploded prematurely, destroying two floors of a hotel and killing the assassin. There is a shrine dedicated to this man in Iran that says, “Martyred in London, 3 August 1989. The first martyr to die on a mission to kill Salman Rushdie.”

Bookstores in both the United States and England were threatened, bombed, and burned down. The threat of violence was so pervasive that a third of bookstores in the US refused to carry the book, while some of the others kept it under the counter. Translators and publishers were assaulted and murdered. Yes, murdered.

So just what was it about this book that stirred up such hatred and violence? Well basically Rushdie insulted the entire Islamic religion as well as probably every possible thing that Muslims hold sacred and dear. There were a LOT of things in the book that offended Muslims, but the three major no-no’s were as follows:

“He referred to Muhammad as ‘Mahound,’ a medieval Christian designation that implied Muhammad was some kind of false deity. He gave the names of Muhammad’s wives to twelve prostitutes in a brothel. And most controversially, he invoked a discredited tradition in Islam, the so-called “satanic verses,” in which Satan inspired Muhammad to compromise with the people of Mecca and to allow them to continue to worship other deities in an attempt to lure them to Islam.”

Rushdie is a smart man, a prolific writer, and he came from a Muslim family so he had to know this book wasn’t going to go down well at all, upon publication. The man’s either a lunatic, an egomaniac, or a genius. Probably all three. 

4. Lolita, 1955 (Vladimir Nabokov)


First sentence:

Lolita, light of my life, fire of my loins. My sin, my soul. Lo-lee-ta: the tip of the tongue taking a trip of three steps down the palate to tap, three on the teeth. Lo.Lee.Ta

One of the most amazing, controversial, analyzed, and taboo books of all time, Lolita is the story of Humbert Humbert a man obsessed with Lolita, a pre-teen girl. On the outside Humbert appears normal: sophisticated, well-spoken, charming, handsome, but inside he churns with an overwhelming desire for his “nymphet,”Lolita. He arranges everything in his life so that he can be near her. He marries her mother, whom he despises, just to get closer to her. And when another man takes Lolita away he chases after her for years; his desire knows no end…no respite. This is a story of obsession, jealousy, and deviant addictions. The book was immediately criticized and banned in several places for the themes and descriptions.

The most disturbing thing about this novel is the obsession itself, the chase, the carrot on a stick; Humbert acts as if he himself has absolutely no control over it. Like he’s being dragged along on a string, inside of a labyrinth. Sadly this is how a lot of professionals describe real-life predators, as addicts who cannot ever stop doing it or wanting it. Shells of men, consumed with overpowering addictions that haunt them day and night.

3. Gravity’s Rainbow, 1973 (Thomas Pynchon)


First sentence:

A screaming comes across the sky.

Gravity’s Rainbow is one of the craziest, longest, most difficult, most confusing, most insane books ever. Ever. It’s pretty much impossible to summarize, understand, or even finish (I got approximately a third of the way through before my mind started to unravel). The only other novels that come to mind with the same level of difficulty are Ulysses by James Joyce or The Recognitions by William Gaddis. Compared to Gravity, Infinite Jest, Atlas Shrugged, and Asbalom Absalom are all light breezy romance novels you would pick up to go to the beach on a sunny day. After trying to come up with ways of describing this monster I just decided to share what these other writers wrote because they do a much better job than I ever could.

The setting is World War II, and England is being devastated by Hitler’s revenge weapon, the V-2 rocket. In response to this, two organizations, ACHTUNG–Allied Clearing House, Technical Units, Northern Germany; and PISCES–Psychological Intelligence Schemes For Expediting Surrender, embark on a quest which will carry them across the world in order to find a solution for this dilemma. That’s about as simple as it gets; a cursory analysis of this story is comparable to trying to sum up the machinations of Astrophysics in Haiku form.”

“It is a Jeremiad, an encyclopedia of cultural minutiae, an historical novel, a catalogue of operas, an anatomy of illicit perversions and mindless pleasures, a book in which you are likely to read an equation of describing the gyroscopic stabilizers of a V-2 rocket as you are to find a Porky Pig cartoon. Coprophilia and rooftop Banana gardens exist in a singularly bizarre harmony, repelling and enticing in equal measure.”

In 1974, Rainbow received the National Book Award and should have won the Pulitzer Prize for fiction as well (all the judges voted for it) but the advisory board thought the novel was too obscene and unreadable to be selected. Thus, 1974 remains the only year since its inception that there isn’t a Pulitzer Prize winner for Fiction.

While I didn’t finish Gravity, I still really really enjoyed parts of it. And I get the feeling the whole book really does make sense and is tied together coherently if you spent an entire lifetime analyzing it. It’s written amazingly well, and some parts of it you actually can process and comprehend, but just when you think you’re starting to figuring it out and really get into it, Pynchon will go into some eighteen page narrative about a psychic, telekinetic octopus or a S&M Coprophilia session, the whole time referencing characters you haven’t even been introduced to yet….or have completely forgotten about because he hasn’t mentioned them in two-hundred pages. Pynchon knew how to write simple declarative sentences. He knew how to write a plot that you could follow. The man just wanted all of us to pull our hair out.

2. Last Exit to Brooklyn, 1964 (Hubert Selby Jr.)


First sentence:

They sprawled along the counter and on the chairs.

Last Exit to Brooklyn doesn’t follow conventional rules of grammar; it uses slang-like conjunctions of words such as “tahell” or “yago”. It forgoes quotation marks, and employs slashes instead of apostrophes.

But it’s not the grammar that makes this book stand out; Exit is not comparable to anything else; it sits uniquely alone on its own shelf in the history of literature. It is one of the saddest, most disturbing, most provoking, most shocking books ever written. Selby’s narrators are voices in the dark, screaming out in rage, surrounded by violence, addiction, degradation, and depravity. Be warned, this book will not cheer you up. Like not even a tiny bit. Like seriously. Not at all.

While the plots of the stories only loosely tie in with each other, the voices are all the same voice. Lost, lonely, weak people, simultaneously abused and abusive, trying to discover and dig out some place of their own in the world. The stories deal with transvestism, hatred, racism, greed, prostitution, domestic violence, and drug addiction.

And it’s not even the topics themselves that make this book so controversial. It’s the way Selby describes them… as if you’re there, as if a buddy of yours is telling you about all this ugly stuff that happened. His writing has a way of getting into your head like very few other writers can. And he doesn’t judge these flawed characters or their horrible actions; he just tells you about them…like he’s sitting in a corner watching it all take place. And unlike Ellis, Selby somehow makes us feel something akin to sadness or empathy for these broken people and their broken lives.

And for all your kids out there, Selby also wrote Requiem for a Dream, which was later made into quite a controversial (and amazing) movie, starring Ellen Burstyn. Selby actually had a small a cameo in the movie.

On the set, he kind of had a huge crush on Burstyn. In real life, Selby was the exact opposite of what you would expect: a kind, sad, unlucky, unhealthy, funny, awesome, lonely, old guy. Burstyn and Selby actually became really good pals. She thought he was so cute and funny and kind…like a little puppy.

And he was in love with her. You could just tell. 

1. Atlas Shrugged, 1957 (Ayn Rand)


First sentence:

“Who Is John Galt?”

Atlas Shrugged rubs a LOT of people the wrong way. In this book, Rand’s heroes all believe in, and practice her philosophy of “objectivism”. Objectivism is the philosophy of rational individualism founded by Rand herself. She describes it as the, “concept of man as a heroic being, with his own happiness as the moral purpose of his life, with productive achievement as his noblest activity, and reason as his only absolute.” In other words, only the strong, productive, and rational in the world have meaning. Everyone else is a “looter.” There is no room for any form of weakness, or laziness, or irrationality. The worst sin is to just sit around and do nothing…to be helpless, to be passive, to pretend to not to understand how the world really works.

In the book, the heroes of the book all eventually go to a new “Atlantis” leaving the weak behind to fend for themselves. With no one strong left to hold up the world it crumbles on top of all the weakness and self-pity.

Rand praised capitalism and saw the dollar sign as the most motivating and inspiring symbol the human species had ever conceived of. Competition was good. Expansion was good. She loathed socialism and welfare. She dismissed religion as a creation by the weak to justify their own weakness and powerlessness. She thought we were all responsible for ourselves…our own life…our own happiness and that anyone who wasn’t happy was weak, and therefore deserved to be unhappy. If you couldn’t add something to society than you didn’t deserve to be alive.

You can imagine that this upset people all across the board: the weak, the poor, the sick, the depressed, the sexist, the forgotten, the infirm, and the empathetic. Not to mention, Christians, Catholics, Protestants, Socialists, editors, and critics. She pretty much offended everyone…but to be fair she also inspired a lot of people. In a recent Book-of-the-month-club poll, Atlas Shrugged was picked as the second most influential book ever written, behind only the Bible.

Atlas itself represents what someone who follows Rand’s philosophy can actually achieve. It is one of the longest books ever written in the English language (certainly the longest by a non-native English speaker) and it is one of the very absolute best novels ever written. Even if you do not believe in most of Rand’s ideals (admittedly some of them are a little zany and romantic) the story itself is what really makes this book stand out. Her characters. Her descriptions of the American landscape and cities. Her descriptions of the villains. Her descriptions of the people who move and shape the world.

Ian is an unemployed thirty-year-old who lives with his mother. He wonders a lot about how he could have started reading comic books at age 30. He has some of his fiction published in a blog in Seoul.

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  1. beyondliberal on

    I’m very surprised “Running with Scissors” isn’t on the list. I’m sure it must have been banned SOMEWHERE, as the story is incredibly disturbing.

    • republicansir on

      Never read that one. I own it though. Some people close to me loved that book. Ill have to drag it out of the attic

  2. As far as I can tell, it appears that most developers test to make something work, not to break it. I have never encountered the lessening return, however the other side where stripped down testing is finished.

  3. Ian Presnell on

    What this is pretty much the best list EVER!! Although I’m probably bias because I wrote it. Update* I do actually have a paper route now and have a “real job” in the works. haha

  4. An extremely interesting list ,thank you ! Although I do find Although a bit overrated.