My favorite books about characters who are down and out

Why am I passionate about this?

All of the books on my list are about characters who—either due to their own failings and character flaws, or bad luck, or the body blows that life has thrown their way, or a combination of all those things—have hit rock bottom (though as it sometimes turns out, there’s a bottom below that bottom). I think because of my own struggles, and because I’ve often been my own worst enemy, I’ve found comfort in reading stories of this sort. Like many of the writers on my list, I’ve also found that, more often than not, the only way out was to start writing about what I was going through. 


I wrote...

The Only Way To Play It

By Peter Alson,

Book cover of The Only Way To Play It

What is my book about?

Five years ago, playing poker in New York’s sketchy underground clubs seemed like the perfect way for artist Nate Fischer to pay his bills. But marriage and parenthood have upped the stakes. With his once-promising art career in freefall, his marriage in trouble, and his ex-con father a lodestone around his neck, Nate knows that on any given night, a bad beat could mean the collapse of his house-of-cards life. When one of his buddies is shot and killed in front of him, it triggers a chain reaction that’s the final straw for Nate’s wife. Forced to confront the true cost of his choices, Nate, finds himself banished to his tiny painting studio along with his just-evicted dad, the one guy who knows exactly where this kind of story ends.

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

The books I picked & why

Book cover of The Gambler

Peter Alson Why did I love this book?

This is one of my favorite “Down and Out” novels of all time, but what makes it even more meaningful is knowing how desperate Dostoyevsky was when he wrote it. Himself a compulsive gambler, Dostoyevsky had managed through his addiction to roulette to dig himself such a deep hole that in order to pay off his creditors, he was forced to borrow the money from his publisher, but only under the condition that he turn in his next book within six weeks or everything he wrote thereafter would belong to the ruthless bastard in perpetuity. Knowing he had to write something he knew intimately in order to meet this absurd deadline, Dostoyevsky wrote about a character not unlike himself. The result is this slim, nearly perfect novel, a fever dream of compulsion in which I felt I was experiencing the highs and lows of the hero as if he were not a stand-in for the author but for me, the reader.

By Fyodor Mikhailovich Dostoyevsky,

Why should I read it?

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

What is this book about?

"The Gambler" is a gripping narrative of the dangers of an addiction to gambling. As was common with Dostoyevsky's writing he draws upon his own life in a semi-autobiographical way in "The Gambler". Dostoyevksy himself suffered from a compulsion to gambling and those first-hand experiences bring a depth of realism to "The Gambler" and to his portrayal of the main character, Alexis Ivanovitch, a young man addicted to gambling. "The Gambler" is an insightful look at the compulsive nature of the gambling addict and the tragic consequences of such an addiction.


Book cover of Cassidy's Girl

Peter Alson Why did I love this book?

Nearly every Goodis novel features an antihero who has fallen from a higher station in life and is now living on the fringes. In this one, Jim Cassidy, once a highly respected airline pilot until a disastrous plane crash leaves him a broken man, now finds himself driving a bus on a dead-end route, consoling himself with a drink at the neighborhood watering hole where he met his cheating wife and trying to figure out how not to get dragged down even deeper. Of course, things do get even worse for him, and not even the surprising “happy ending” can change the inevitability of the ultimate crash we know is coming for him and for all of us.

By David Goodis,

Why should I read it?

1 author picked Cassidy's Girl as one of their favorite books, and they share why you should read it.

What is this book about?

They say that a man needs a woman to go to hell with. Cassidy had two. One was Mildred, the wife who kept him chained with ties of fear and jealousy and paralyzing sexual need. The other was Doris, a frail angel with a 100-proof halo and a bottle instead of a harp. With those two, Cassidy found that the ride to hell could be twice as fast.

Goodis holds his rightful place in the pantheon of noir writers, alongside Jim Thompson, Cornell Woolrich, and Charles Williams. His writing stays true and never wavers, is never prettified. His characters always…


Book cover of Ask the Dust

Peter Alson Why did I love this book?

This tale of Arturo Bandini, a young would-be writer living on the edge in 1930s Los Angeles, is the book that Charles Bukowski discovered in a local library and was purportedly his inspiration for becoming a writer himself. Like Henry Chinaski in Buk’s autobiographical works, Bandini is a stand-in for Fante, and his personal disasters are mined for their comic gold. He falls in love with a waitress named Camilla, only to watch her fall in love with another man and eventually suffer a nervous breakdown. In the end, Bandini realizes he can't help Camilla and must focus on his writing instead—a conclusion that I, as a young writer, totally identified with.

By John Fante,

Why should I read it?

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

What is this book about?

Ask the Dust is a virtuoso performance by an influential master of the twentieth-century American novel. It is the story of Arturo Bandini, a young writer in 1930s Los Angeles who falls hard for the elusive, mocking, unstable Camilla Lopez, a Mexican waitress. Struggling to survive, he perseveres until, at last, his first novel is published. But the bright light of success is extinguished when Camilla has a nervous breakdown and disappears . . . and Bandini forever rejects the writer’s life he fought so hard to attain.


Book cover of Fat City

Peter Alson Why did I love this book?

Denis Johnson loved and studied this novel so much that he had to swear it off lest it give him a complex about his own writing. I totally relate. Spare and beautiful, full of wistful melancholy, Gardner’s tale about a friendship between two boxers, one on the way up, one on the way down, but both of them headed toward the same dead-end future, perfectly captures the California bleakness that I’ve also encountered when reading two other favorites, Joan Didion and Raymond Chandler. 

By Leonard Gardner,

Why should I read it?

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

What is this book about?

'Tremendous' Geoff Dyer

'A pitch-perfect account of boxing, blue-collar bewilderment and the battle of the sexes' San Francisco Chronicle

A major cult film directed by John Huston

Stockton, California: a town of dark bars and lunchrooms, cheap hotels and farm labourers scratching a living. When two men meet in the Lido Gym - the ex-boxer Billy Tully and the novice Ernie Munger - their brief sparring session sets a fateful story in motion, initiating young Munger into the "company of men" and luring Tully back into training.

Fat City is a vivid novel of defiance and struggle, of the potent…


Book cover of A Fan's Notes

Peter Alson Why did I love this book?

Exley’s “fictional autobiography” charts with comic brilliance his struggles with mental illness and alcoholism, his obsession with USC classmate Frank Gifford, the golden boy of college football, whose successes and failures as a member of pro football’s New York Giants, come to be a way for Exley to look past his own inadequacies, so much did he invest in and identify with Gifford as he watched each Sunday from the bleachers of the Polo Grounds. He writes: “Each time I heard the roar of the crowd, it roared in my ears as much for me as him; that roar was not only a promise of my fame, it was its unequivocal assurance.” In fact, it is from the depths of despair that his fantasies helped distract him from, that Exley finds actual fame and salvation in sitting down to write this book. We can all be grateful that he did.

By Frederick Exley,

Why should I read it?

3 authors picked A Fan's Notes as one of their favorite books, and they share why you should read it.

What is this book about?

The narrator of this tale is the ultimate unreconstructed male. his primary concerns are booze, sex and the New York Giants. But things go very wrong for him - he drinks too much, he's impotent, and the Giants start to lose. So we follow his trail, through failed marriages, to mental hospital.


You might also like...

Luck of the Irish

By Kate Darroch (editor),

Book cover of Luck of the Irish

Kate Darroch Author Of Death in Paris

New book alert!

Why am I passionate about this?

Living on Devon's gorgeous coast, I'm melding my lifelong love of reading Cozy Sleuths with my love of writing and years of living in foreign climes to write Travel Cozies. I also have a Vella Heist serial Found Money starting on Vella soon, and a Cozy Spy series They Call Him Gimlet coming out in the Autumn.

Kate's book list on humorous murder mysteries

What is my book about?

Ten Tantalizing Cozy Mysteries to enjoy on Saint Patrick's Day! Sure to make you chuckle and keep you guessing! Plus, the authors' favorite Saint Patrick's Day Recipes.

Have fun curling up with these Cozy stories and a delicious drink, knowing that just by enjoying these tales you are doing good in the world as well - because 100% of book sales proceeds go to a non-profit helping children living in terrible conditions (through the non-profit RAICES Texas). 

Luck of the Irish

By Kate Darroch (editor),

What is this book about?

Ten Tantalising Cozy Mysteries to enjoy on Saint Patrick's Day! Sure to make you chuckle, make you go "aawww", maybe even raise goosebumps,too - or a bump of curiosity! Plus the authors' favorite Saint Patrick's Day Recipes.

Have fun curling up with these Cozy stories and a delicious drink, knowing that just by enjoying these tales you are doing good in the world as well - because 100% of book sales proceeds go to a non-profit helping children living in terrible conditions, RAICEStexas.org


Topics
  • Coming soon!

5 book lists we think you will like!

Interested in gambling, romantic love, and presidential biography?

10,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about gambling, romantic love, and presidential biography.

Gambling Explore 40 books about gambling
Romantic Love Explore 827 books about romantic love
Presidential Biography Explore 18 books about presidential biography