Fans pick 100 books like Leaving Las Vegas

By John O'Brien,

Here are 100 books that Leaving Las Vegas fans have personally recommended if you like Leaving Las Vegas. Shepherd is a community of 12,000+ authors and super readers sharing their favorite books with the world.

When you buy books, we may earn a commission that helps keep our lights on (or join the rebellion as a member).

Book cover of Fear and Loathing in Las Vegas

Tim O'Leary Author Of Men Behaving Badly

From my list on characters you love to hate.

Why am I passionate about this?

My name is Tim O’Leary and two of my books, Dick Cheney Shot Me in the Face–And Other Tales of Men in Pain and Men Behaving Badly, emanate from the minds of protagonists trying to do the right thing the wrong way or evil characters doing the wrong thing they believe to be right. I’m particularly drawn to those wonderful literary psychopaths that draw you in with compelling personalities, while reviling the reader with their heinous actions. 

Tim's book list on characters you love to hate

Tim O'Leary Why did Tim love this book?

I found this book in college, and at the time, I thought it was the most unique book I had ever read.

Thompson’s “Gonzo Journalism” was fresh, funny, and thought-provoking, with a subtext of modern poetry, political activism, and a sense of humor I have never seen replicated.

By Hunter S. Thompson,

Why should I read it?

11 authors picked Fear and Loathing in Las Vegas as one of their favorite books, and they share why you should read it.

What is this book about?

'We were somewhere around Barstow on the edge of the desert when the drugs began to take hold. I remember saying something like, "I feel a bit lightheaded; maybe you should drive ..."'

Hunter S. Thompson is roaring down the desert highway to Las Vegas with his attorney, the Samoan, to find the dark side of the American Dream. Armed with a drug arsenal of stupendous proportions, the duo engage in a surreal succession of chemically enhanced confrontations with casino operators, police officers and assorted Middle Americans.

This stylish reissue of Hunter S. Thompson's iconic masterpiece, a controversial bestseller when…


Book cover of The Basketball Diaries: The Classic about Growing Up Hip on New York's Mean Streets

Andrew Mann Author Of Such Unfortunates

From my list on stories so powerful you have to read them twice.

Why am I passionate about this?

I have expertise and a passion for this topic because I suffered from a terrible addiction to drugs for many years and was considered a hopeless case. If I can beat my addiction then anyone can!

Andrew's book list on stories so powerful you have to read them twice

Andrew Mann Why did Andrew love this book?

This was another true story of someone who suffered a terrible addiction and was able to overcome it. I liked it because Jim was a regular guy and not a celebrity sharing his life story as so many of these book are. It was one of the first books that gave me inspiration to write a book. It also became a movie where Leonardo DeCaprio played Jim Carrol.

By Jim Carroll,

Why should I read it?

3 authors picked The Basketball Diaries as one of their favorite books, and they share why you should read it.

What is this book about?

The urban classic coming-of-age story about sex, drugs, and basketball

Jim Carroll grew up to become a renowned poet and punk rocker. But in this memoir of the mid-1960s, set during his coming-of-age from 12 to 15, he was a rebellious teenager making a place and a name for himself on the unforgiving streets of New York City. During these years, he chronicled his experiences, and the result is a diary of unparalleled candor that conveys his alternately hilarious and terrifying teenage existence. Here is Carroll prowling New York City--playing basketball, hustling, stealing, getting high, getting hooked, and searching for…


Book cover of Methland: The Death and Life of an American Small Town

Russell C. Crandall Author Of Drugs and Thugs: The History and Future of America's War on Drugs

From my list on what the war on drugs is really about.

Why am I passionate about this?

Over my two decades as a scholar of American foreign policy and international politics, I had multiple opportunities to serve as a Latin America foreign policy aide. Given that Latin America plays a central role in the U.S.-hatched modern war on drugs, much of my policymaking was directly or indirectly tied to drug policy. I thus wrote Drugs and Thugs above all to make sure that I had a good sense of the history of this seemingly eternal conflict, one that is “fought” as much at home as abroad. 

Russell's book list on what the war on drugs is really about

Russell C. Crandall Why did Russell love this book?

Reding’s book on the methamphetamine epidemic in small-town Ohio is distressing but essential. He is exceptional in showing rather than telling how meth is in so many ways the Great American Drug. It makes you work even more maniacally, for one. And the hollowing out of Middle America makes the drug’s proactive nature even more attractive in these forgotten towns and cities. It is painful that the meth scourge might have eased but, as is so often the case, other destructive substances have quickly replaced it. 

By Nick Reding,

Why should I read it?

2 authors picked Methland as one of their favorite books, and they share why you should read it.

What is this book about?

A New York Times Bestseller
Winner of the Chicago Tribune Heartland Prize
Winner of the Hillman Prize for Book Journalism

Named a best book of the year by:
the Los Angeles Times
the San Francisco Chronicle
the Saint Louis Post-Dispatch
the Chicago Tribune
the Seattle Times

"A stunning look at a problem that has dire consequences for our country.”-New York Post

The dramatic story of Methamphetamine as it comes to the American Heartland-a timely, moving, account of one community's attempt to confront the epidemic and see their way to a brighter future.

The bestselling book that launched meth back into…


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Book cover of At What Cost, Silence?

At What Cost, Silence? By Karen Lynne Klink,

Secrets, misunderstandings, and a plethora of family conflicts abound in this historical novel set along the Brazos River in antebellum Washington County, East Texas.

It is a compelling story of two neighboring plantation families and a few of the enslaved people who serve them. These two plantations are a microcosm…

Book cover of Requiem for a Dream

Craig McGuire Author Of Carmine and the 13th Avenue Boys: Surviving Brooklyn's Colombo Mob

From my list on diving deep into the dark side of Brooklyn.

Why am I passionate about this?

It’s no wonder South Brooklyn, in the latter half of the last century, is the setting for so many remarkable dramas for both page and screen. In fact, when legendary former NYPD Detective Thomas Dades offered to make introductions to a Colombo Crime Family associate who cooperated with the federal government, I leapt at the opportunity. I was born in Greenpoint in 1971 and grew up on 16th Avenue in the heart of Bensonhurst. It’s not just South Brooklyn’s raw, urban chaotic physical setting, but the sheer volatility of this period in time, where so many transformational trends of the larger culture were evident, and some even epi-centered.

Craig's book list on diving deep into the dark side of Brooklyn

Craig McGuire Why did Craig love this book?

Hubert Selby Jr. delivers another dark indictment of life along the outer shores of South Brooklyn, in the form of both this 1978 novel and the grim 2000 film Darren Aronofsky film adaptation (co-written with Selby, with a cameo as prison guard).

The characters of this disturbing drama are as marginalized as the bleak 1970s backdrop they infect. Selby’s prose holds us by the back of the neck as his characters descend down awful spirals of addiction: Sara Goldfarb with her diet pills, and her son Harry, his girlfriend Marion, and his best friend Tyrone, all heroin addicts. Electroconvulsive therapy, reluctant prostitution, and amputation abound, harrowing hallmarks you’d expect from Selby.

For this trip to Coney Island, think more Warriors, less Woody Allen, and buckle up. It’s going to be a spectacularly gruesome ride.

Locations of interest: Coney Island Clam Bar; Brighton Beach Boardwalk; Surf Avenue Second-hand Shops; 3152 Brighton…

By Hubert Selby Jr.,

Why should I read it?

3 authors picked Requiem for a Dream as one of their favorite books, and they share why you should read it.

What is this book about?

Harry Goldfarb, heroin addict and son of lonely widow Sara, cares only about enjoying the good life with girlfriend Marion and best friend Tyrone C Love, and making the most of all the hash, poppers and dope they can get. Sara Goldfarb sits at home with the TV, dreaming of the life she could have and struggling with her own addictions - food and diet pills. But these four will pay a terrible price for the pleasures they believe they are entitled to. A passionate, heart-breaking tale of the crushing weight of hope and expectation, Requiem for a Dream is…


Book cover of No Longer Human

Keijo Kangur Author Of The Nihilist

From my list on alienation and self-destruction.

Why am I passionate about this?

I have always liked antiheroes and characters that are in some way doomed. To me, there’s something romantic about them. And over time I have come to replace the fictional protagonists of noir and horror with antiheroes from real life. With miserable authors who wrote about their own lives, where instead of gangsters or monsters, they waged battle against themselves, against their own demons and despair. Books like these have kept me company during some of the darkest periods of my life, and their unflinching honesty has inspired me to become a writer. Perhaps they can do the same for you.

Keijo's book list on alienation and self-destruction

Keijo Kangur Why did Keijo love this book?

Told with unflinching honesty, this dark Japanese classic is often considered a kind of suicide note by its author, who killed himself shortly before its publication.

Whilst I cannot say that I’ve necessarily gone through some of the extreme experiences of its protagonist, I can nevertheless say that I’ve experienced a very similar sense of alienation, which has at times made me feel less than human, making this one of the most relatable books that I have ever read.

Considering its contents, I should probably not tell that to my psychiatrist. I'm just kidding; I don’t have one. However, considering the book’s classic status, it seems that I am far from the only one who relates to its author’s struggles.

By Osamu Dazai, Donald Keene (translator),

Why should I read it?

4 authors picked No Longer Human as one of their favorite books, and they share why you should read it.

What is this book about?

Portraying himself as a failure, the protagonist of Osamu Dazai's No Longer Human narrates a seemingly normal life even while he feels himself incapable of understanding human beings. Oba Yozo's attempts to reconcile himself to the world around him begin in early childhood, continue through high school, where he becomes a "clown" to mask his alienation, and eventually lead to a failed suicide attempt as an adult. Without sentimentality, he records the casual cruelties of life and its fleeting moments of human connection and tenderness.


Book cover of The Fuck Up

Keijo Kangur Author Of The Nihilist

From my list on alienation and self-destruction.

Why am I passionate about this?

I have always liked antiheroes and characters that are in some way doomed. To me, there’s something romantic about them. And over time I have come to replace the fictional protagonists of noir and horror with antiheroes from real life. With miserable authors who wrote about their own lives, where instead of gangsters or monsters, they waged battle against themselves, against their own demons and despair. Books like these have kept me company during some of the darkest periods of my life, and their unflinching honesty has inspired me to become a writer. Perhaps they can do the same for you.

Keijo's book list on alienation and self-destruction

Keijo Kangur Why did Keijo love this book?

It takes courage to name your book that. Especially in the 90s before self-publishing became a thing. Which did not stop its renegade author from selling xeroxed copies of it in the streets.

Its titular protagonist, who is jobless and homeless after his girlfriend kicks him out, is based on the author himself. He struggles with feelings of inadequacy and a sense of purposelessness. He works odd jobs, writes an occasional poem, meets eccentric strangers, engages in substance abuse, and gets into sticky situations on account of his bad decisions.

While I don’t know about you, I can strongly relate to the character. The book's dark humor is also enough to make it one of my favorites.

By Arthur Nersesian,

Why should I read it?

1 author picked The Fuck Up as one of their favorite books, and they share why you should read it.

What is this book about?

Arthur Nersesian's underground literary treasure is an unforgettable slice of gritty New York City life...and the darkly hilarious odyssey of an anonymous slacker. He's a perennial couch-surfer, an aspiring writer searching for himself, and he's just trying to survive. But life has other things in store for the fuck-up. From being dumped by his girlfriend to getting fired for asking for a raise, from falling into a robbery to posing as a gay man to keep his job at a porn theatre, the fuck-up's tragi-comedy is perfectly realised by Arthur Nersesian, who manages to create humour and suspense out of…


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Book cover of Ferry to Cooperation Island

Ferry to Cooperation Island By Carol Newman Cronin,

James Malloy is a ferry captain--or used to be, until he was unceremoniously fired and replaced by a "girl" named Courtney Farris. Now, instead of piloting Brenton Island’s daily lifeline to the glitzy docks of Newport, Rhode Island, James spends his days beached, bitter, and bored.

When he discovers a…

Book cover of The Fire Within

Keijo Kangur Author Of The Nihilist

From my list on alienation and self-destruction.

Why am I passionate about this?

I have always liked antiheroes and characters that are in some way doomed. To me, there’s something romantic about them. And over time I have come to replace the fictional protagonists of noir and horror with antiheroes from real life. With miserable authors who wrote about their own lives, where instead of gangsters or monsters, they waged battle against themselves, against their own demons and despair. Books like these have kept me company during some of the darkest periods of my life, and their unflinching honesty has inspired me to become a writer. Perhaps they can do the same for you.

Keijo's book list on alienation and self-destruction

Keijo Kangur Why did Keijo love this book?

This book is about a heroin addict. However, you don’t need to be a heroin addict to sympathize with its protagonist’s existential weariness—or ennui, as the French call it. I know I do. After exiting a rehabilitation clinic, he wanders around listlessly, visiting friends and acquaintances, trying to find a reason to go on, yet finding none.

The story may be better known for the excellent film adaptation by Louis Malle—which switches heroin for alcohol—yet the terse and evocative writing of the original novel nevertheless packs a punch. The fact that the protagonist was closely inspired by the author’s friend lends an element of authenticity to it, making his suffering all the more relevant.

By Pierre Drieu La Rochelle, Richard Howard (translator),

Why should I read it?

1 author picked The Fire Within as one of their favorite books, and they share why you should read it.

What is this book about?

Adapted to film by both Louis Malle and Joachim Trier, this heart-rending and tenderly wrought novel narrates the decline of an artist and heroin addict in 1920s Paris.

Pierre Drieu la Rochelle might be said to be both the Hemingway and the Fitzgerald of twentieth-century French literature, a battle-scarred veteran of the First World War whose work chronicles the trials and tribulations of a lost generation, a man about town, a heartbreaker with a broken heart, a literary stylist whose work is as tough as it is lyrical and polished. Politically compromised as Drieu came to be by his affiliation…


Book cover of The Drinker

Keijo Kangur Author Of The Nihilist

From my list on alienation and self-destruction.

Why am I passionate about this?

I have always liked antiheroes and characters that are in some way doomed. To me, there’s something romantic about them. And over time I have come to replace the fictional protagonists of noir and horror with antiheroes from real life. With miserable authors who wrote about their own lives, where instead of gangsters or monsters, they waged battle against themselves, against their own demons and despair. Books like these have kept me company during some of the darkest periods of my life, and their unflinching honesty has inspired me to become a writer. Perhaps they can do the same for you.

Keijo's book list on alienation and self-destruction

Keijo Kangur Why did Keijo love this book?

The novel’s protagonist is initially successful. Then something or other drives him towards drink, and soon he cannot get enough. His downward spiral is quick. He abandons his morals and starts associating with shady characters, lying, and stealing.

The book’s author, a successful writer in his time, was also a troubled man suffering from morphine addiction and alcoholism. The latter is intimately portrayed in this largely autobiographical novel, which was written in a nazi insane asylum and published posthumously.

Yet despite all the trouble that the novel’s self-destructive protagonist inflicts upon himself, I cannot help but feel sorry for him. He is clearly driven on by some demon he can neither resist nor understand. And some of us, including me, have felt the same.

By Hans Fallada,

Why should I read it?

1 author picked The Drinker as one of their favorite books, and they share why you should read it.

What is this book about?

One of the great German writers of the 20th century draws from his own life to present a “brave, fearless, and honest” tale of one man’s dark descent into depression and alcoholism (The Sunday Times, London)
 
This astonishing, autobiographical tour de force was written by Hans Fallada in an encrypted notebook while he was incarcerated in a Nazi insane asylum. Discovered after his death, it tells the tale—often fierce, often poignant, often extremely funny—of a small businessman losing control as he fights valiantly to blot out an increasingly oppressive society.

In a brilliant translation by Charlotte and A.L. Lloyd, it…


Book cover of Madeleine

Jody Hadlock Author Of The Lives of Diamond Bessie

From my list on 19th century prostitutes.

Why am I passionate about this?

As a young teenager, I lived in a small Texas town and loved touring the Victorian “gingerbread” homes full of antiques. I had an overwhelming desire to time travel back to the mid-1800s. When I learned of Diamond Bessie’s story, I was immediately intrigued because of the period, and also by the circumstances of her life. Why does a woman enter the world’s oldest profession? I discovered that I absolutely love research and “time traveled” back to that era by devouring everything I could get my hands on about life in the 19th century, especially for a marginalized woman like Bessie. 

Jody's book list on 19th century prostitutes

Jody Hadlock Why did Jody love this book?

In my quest to learn about the inner lives of 19th-century prostitutes, I found three memoirs, all gold mines. Demi-mondaines always used a stage name and that’s what the eponymous Madeleine chose. Even though she wasn’t a writer by trade, her story as a young “public woman” in the 1890s is riveting, and heartbreaking. When Madeleine’s autobiography was first published by Harper & Brothers in 1919, it caused a scandal and led to a lawsuit against the publisher. Harper eventually successfully defended itself but still ended up withdrawing the book from circulation. It wouldn’t be available to the public again for nearly 70 years. 

By Marcia Carlisle, Ben B. Lindsey,

Why should I read it?

1 author picked Madeleine as one of their favorite books, and they share why you should read it.

What is this book about?

An insider's eloquent, moving account of life as a nineteenth century prostitute. This memoir offers a vivid account of brothel life in 1890s North Americain the city (Chicago, St. Louis), the Western boom town (Butte, Montana), and on the Canadian frontier. Containing the introductions to the 1919 and 1986 editions (by Judge Ben B. Lindsey and scholar Marcia Carlisle, respectively), its eponymous narrator offers great insight into the daily workings of both "high" and "low" class houses, as well as her relationships with madams, clientele, and members of the "legitimate" society in which prostitution flourished.


Book cover of Common Women: Prostitution and Sexuality in Medieval England

Cara Hogarth Author Of My Lady of the Whip

From my list on medieval sexuality.

Why am I passionate about this?

Cara Hogarth emigrated from England to Australia as a child, but always wished she hadn’t. So she studied medieval history at university in order to travel back in time and place. Now that she’s bagged a PhD (on Chaucer’s raunchy Wife of Bath), she prefers to write historical fiction in order to truly immerse herself and her readers in the past. She finds academic history a fantastic inspiration for her fiction writing, but is always seeking out historical novels that hit just the right balance between research, humor, and page-turning plot. Warning: her novels can get quite steamy!

Cara's book list on medieval sexuality

Cara Hogarth Why did Cara love this book?

Published by Oxford University Press, Common Women is an academic rather than a popular history of medieval English prostitution, and its author is an expert in medieval sexuality.

I adore the wealth of historical detail founded on original research that Karras presents. It’s a goldmine of inspiration for those of us who write fiction set in medieval England. Where else can you learn about the cross-dressing prostitute John Rykener, the Bishop of Winchester’s brothel empire in Southwark, or discover names like Clarice Clatterballock?

By Ruth Mazo Karras,

Why should I read it?

1 author picked Common Women as one of their favorite books, and they share why you should read it.

What is this book about?

An account of the lives of prostitutes in Medieval England relations, which covers their treatment under the law, and concludes that prostitution was central to the medieval understanding of feminity.


Book cover of Fear and Loathing in Las Vegas
Book cover of The Basketball Diaries: The Classic about Growing Up Hip on New York's Mean Streets
Book cover of Methland: The Death and Life of an American Small Town

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Interested in prostitutes, alcoholism, and Las Vegas?

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