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Land of the Lost Souls: My Life on the Streets

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A moving, funny, and unforgettable memoir of homeless life in New York

For the past sixteen years, Cadillac Man has lived on the streets of New York City. Over those years, he has recorded the facts of his daily life, writing hundreds of thousands of words in a series of spiral-bound notebooks. Cadillac My Life on the Streets distills those journals into a memoir of homeless life, full of indelible characters and packed with gripping stories. In a gritty, poignant, and funny voice, Cadillac narrates his descent into homelessness, the struggles and unexpected freedoms of his life, and the story of his love affair with a young runaway, whom he eventually (and tragically) reunites with her family. The United States has seven hundred thousand homeless people; ultimately, Cadillac's story is their story.

304 pages, Hardcover

First published March 17, 2009

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Displaying 1 - 30 of 53 reviews
Profile Image for Jessica.
392 reviews40 followers
June 2, 2011
I come away from this book not really knowing how to feel.

On one hand, I found myself thinking, I’d love to hear the other side of the story. Too many times I was PAINFULLY aware that the story I was getting was a highly edited one sided story that was delivered in exactly the way Cadillac Man wanted you to hear it. My BS meter was going a bit nuts at times.

I have issues with someone painting himself as the hero of his own story. Maybe it’s true, maybe he’s a genuinely nice guy that is always there to help out, to care, to be an angel to those in need. On the other hand, I find myself wondering how he managed to be so available to all the “street people” (his term not mine) but couldn’t stay in his kids lives? It’s a bit of a disconnect for me. So you’re nice to all the hookers and if they are in danger will fight for them, but you can’t make an effort to see your kids? Come on dude. And yes, I find it very nice that you helped bathe one of you fellow men that was sick and dying and filthy, but when was the last time you sent your kid birthday wishes?

Another thing that really didn’t sit well with me is the number of times he resorts to physical violence when there really was no need to. Many of his stories would talk about how someone was wronging someone or in a verbal fight and he would escalate to physical violence when he was in no danger of being hurt. The stories attempted to pass him off as being the ultimate badass, that never lost a fight and everyone was afraid of him. In reality it made him look like someone that couldn’t control himself. Maybe that had something to do with his inability to find/keep a job.

He talks about missing home, wanting to go home, but I honestly can’t see any reason why he can’t have a life off the streets. He isn’t an alcoholic or a drug addict. He doesn’t have a whiff of serious debilitating mental disease. He has no physical infirmities to keep him from working. He was a working man for some time, and lost his job so he has the capacity to work. He mentions he was embarrassed to work at fast food and that it didn’t pay well. This may be an insensitive thing to say but the phrase “beggars can’t be choosers” literally applies here.

Too many times he made excuses, or refused to take responsibility and blamed everyone but himself. He was outraged that he had to go to jail for two years to pay off back child support, granted he agrees that he owes it, he is also upset that his family wouldn’t chip in and pay off his back child support for him so he could avoid jail. Afterwards he moves in with a guy he meet there and lives in the business the guy owns. When after a year the guy wants him to move out he couldn’t understand why? Um, because you’re a fricken mooch that won’t support yourself or your family. He bemoans the fact that he has to apply for jobs and pass interviews instead of just having his friends hook him up like they use to. Hmmmmm… methinks you burned too many bridges and no one was willing to vouch for you anymore.

I want to feel sorry for him. I don’t even know that he wants the reader to feel sorry for him. But I just can’t get there. Compared to others on the street, the deck isn’t that stacked against him. I’m not saying it would be easy to re-enter society as a gainfully employed man with a place to stay, but he has a lot going for him.
Profile Image for Liza.
103 reviews9 followers
March 14, 2010

I received this book through the Goodreads First Reads giveaway that I entered. As soon as it arrived in the mail, I put it at the top of my reading queue. At the time I entered the giveaway, I had never heard of Cadillac Man, nor read any of his excerpted works, which have apparently been stirring up quite a bit of attention for homelessness. Living on the streets Cadillac Man was his own life chronicler, writing about his daily life, both the little things like going canning, receiving free meals and clothes from churches, getting harassed and beaten and the bigger things like the death of a friend, a fellow homeless man.


The Introduction at the beginning of the books reads like a disclaimer from the narrator. Cadillac Man makes no excuses for the nature or content of the stories that he tells, because those stories are his life. One common thread that arises throughout the book is Cadillac Man's refusal to be pitied. He accepts that he made choices in the past that have led to where he is now, and he acknowledgeds that he has always consciously chosen to stay where he is: on the streets.


The nature of Cadillac Man's nature is very approachable. It has a clear storytelling element that most likely derives from the habit of sharing stories on the streets. Each chapter stands alone as its own anecdotal account, often linked to a particular figure in Cadillac Man's life or a certain character on the streets. At the same time each chapter is labeled with the year and burrough, to give a general sense of time and place. Since the chapters are not directly linked, nor even organized chronologically, reading the book straight through can result in some confusion. An event mentioned in an early chapter as having occurred in the is related in a later chapter as though in the present. The reader consequently feels the need to double-check the chronology, or else read the chapters in a different order other than that presented in the published form.


Perhaps the best element about this book is its candor. It isn't that Cadillac Man has no sense of privacy; it's more like he really understands basic human nature. Essentially, we all do have the same biological drives and needs- food, clothing, shelter of some kind, and human interaction. Cadillac Man shows us that this last thing, the need for human interaction, is seemingly the strongest of all. Each chapter of this book is about a connection, a human interaction of some kind. Some chapters are about the loss, erosion or destruction of a human connection.


In the chapter "Irish", Cadillac Man tells about a man called Irish that Cadillac Man met soon after becoming homeless. In a way, Irish saved Cadillac Man from himself and reconnected him to humanity. When Cadillac Man lost Irish, he developed a gaping hole of grief inside just as any other human being would. Also, this loss reverberates in Cadillac Man's relationships with other individuals on the streets, and the threat of this loss is woven throughout the chapter "Penny" and motivates Cadillac Man's decision about the young runaway who inspired love and true human connection in him.


Land of the Lost Souls collects the unabashed stories of Cadillac Man, a thirteen-year veteran of the New York City streets. If his longevity on the streets is not enough to suggest the depth and wealth of his experiences, one need only listen to his words. His character and very identity shine through the stories he tells, and although he does not seem to intend that his stories, the chapters in this book, be read as parables , they often subtly convey certain powerful life lessons.

Profile Image for Darcia Helle.
Author 30 books735 followers
August 15, 2013
I was disappointed in this book. I expected a gritty tale, showing us the truth of what life is like for the homeless. I was hoping for an enlightened look at how average people find themselves on the street, and how difficult it is to find help once there. That is shown here to a small degree, but I found the story almost comically slanted throughout. Cadillac Man portrays himself as the superhero of the streets. When people give him money, he passes it on to the church or other people in need. He refuses to take food or handouts from store owners. Indeed, he watches out for and takes care of all the lost souls, while turning his back on his own daughter.

This leads me to the second reason I found this book impossible to like. Cadillac Man tells us quite honestly that he likes being on the streets. He loves the freedom. He loves not having to answer to a boss or a wife. He does what he wants, when he wants. His reasons for walking out on his family are shallow at best. He would have us believe he is altruistic, helping all his street friends and expecting nothing in return. Yet he leaves his young daughter without a father and without any financial help.

Sadly, I think this book reinforces some people's beliefs that the homeless are on the streets because they want to be. While that is true for some, and certainly it is for Cadillac Man, it is not true for most. This book is a hindrance to all the people who have lost their jobs and their homes, who have no family and nowhere to go, who can't get a job or state aid because they have no address. To me, Cadillac Man is simply a guy who ran from responsibility and is now being glamorized by his own self-indulged words.
Profile Image for Jeff Scott.
767 reviews83 followers
September 13, 2010
From the journals of Cadillac Man (so named when a Cadillac hit him so hard, it left its imprint on his body), comes the story of the homeless.

Cadillac Man has been on the streets for over five years, his story is one of many, but his style is compelling. It's a journal, but it reads like a book of short stories each a different genre style. In Eddie and the Wizard, it reads like a hard-boiled detective novel. Cadillac Man takes on a human leech and his mob to stop him from taking advantage of the weak. There are love stories like Penny, where he helps a runaway go back to the real world. There is his own story which provides a glimpse as to why many are homeless. Many are hurting, feeling that they failed their friends and family, they seem bent on punishing themselves by living on the street.

His own story is told in three parts, overcoming his hard upbringing to create a life with a good job, and a family, all to have it fall apart. He makes a choice to live on the street, seemingly to punish himself for his failures. It also allows him to walk away from pressures and demands, not that he doesn't find plenty of difficulties on the street.

In Penny, the reader can see the difference between the experienced and inexperienced living on the street. Most don't make it two years, he's been out there much longer. The journal criss crosses at different times in his life, some on his background, others to illustrate a point. Overall this is a must read for anyone who wants to know about those living on the street. It's not stories full of empathy and sadness, but frustration, humor, and a little anger that drive the story.
Profile Image for Hectaizani.
733 reviews20 followers
March 29, 2010
The author of this memoir, Cadillac Man, was homeless on the streets of New York City for over thirteen years. For a not well defined reason, he chose to leave behind his wife and children and move into the great outdoors. At first he wanted to die, but when death wasn't forth-coming he then began to embrace his new life of freedom.

According to his narrative, most of his time was spent "canning" or picking up discarded aluminium cans and returning them for the deposit. It paid fairly well, often $50 or more a day. Cadillac Man isn't a drinker or drug addict mostly living off coffee and cigarettes.

The material in the book was culled from a series of spiral-bound journals and it was originally excerpted in Esquire magazine. It deals with his day to day life on the streets, the interactions he shares with other street people, his daily wanderings around the city, and survival tips if one were to find oneself in the same position.

Since the book was published, Cadillac Man's situation has changed. He is now only homeless part-time, otherwise he lives with his girlfriend in Astoria. There was a documentary film made about his life, called "Cadillac Man: Life Under the Viaduct" which was released in 2006 by Hell's Kitchen Films.
Profile Image for Rachel Lee Harris Sagers.
2 reviews3 followers
March 22, 2009
I've often wondered, sitting on the train, passing port authority, about the circumstances that lead someone to a homeless life.

From the varied reasons Cadillac Man reveals in his survival guide to the streets, this one stood out as the most culpable:

"Blue shirt, red tie, black pants, and green sneakers. Perfect. This is not me, an image of the life I once had and don't wish to go back to. I lost everything, and to try again with the chance of failure, I won't risk my sanity."

We, the "outsiders," as Cadillac Man calls us, think living on the sreet is insane. But what home doesn't come with it's own brand of insanity?
Profile Image for Grrlscientist.
163 reviews26 followers
May 12, 2018
The homeless are everywhere in New York City. I run across them every day while riding public transit, while walking around the city and while using wireless in the public libraries. After a few conversations with homeless people, I’ve learned that most of them avoid shelters because of the risk of violent crime there. So where do they sleep? Where do they go to get a shower and clean clothes? Are all homeless people either crazy or crackheads? How did these people end up living on the streets in the first place? Don’t they have families and friends? You will learn the answers to these and other questions in a compelling new memoir, Land of the Lost Souls: My Life on the Streets by Cadillac Man, who lived on the streets of New York for 16 years (Bloomsbury; 2009).

The author introduces his book by writing;


I ain’t no scholar.
I ain’t no bum.
I have never been good in grammar, so there will be misspellings and perhaps some passages that make no sense to you.
But hey, I’m a street person, not a Rhodes Scholar. You, the reader, will just have to bear with me. You’ll see vulgar language, nudity, street jargon, romance, etc. You may laugh or cry or both. You may even say this guy is nuts and should be committed to a padded room with Demerol cocktails. And in a way you’re right. You have to be crazy to live out here, but craziness is a way of survival, which I’ll explain to you later.
These are my people, my friends, my enemies […] This is my story, their story.
Empathy!


Although I don’t recall any misspellings, Cadillac Man does deliver, as promised.

From the moment I began reading this memoir, I was captivated. Despite the sometimes coarse language and odd timing of the details in some of his stories, I think this book works really well. The personalities of the men and women shine from the pages containing their collected stories; some humorous, others poignant, all compelling. Through Cadillac Man’s eyes, we get a rare insider’s glimpse into the lives of homeless people — many of them veterans with peculiar and memorable names like Chocolate Milk, Old Crow, the Wizard, and Twinkies. In this book, we also meet newly destitute families and pimps and prostitutes as well as those who provide a helping hand whenever and where ever they can. We learn about the many trials of street life: poor sleep; violence; bad weather; filth and the constant presence of illness and death. We also pick up a few tips for surviving on the streets: for example, crumpled up newspaper stuffed inside one’s clothing makes good insulation and can also double as toilet paper in a pinch; garbage spread around one’s sleeping place is a good way to hear people sneaking up on you; and refrigerator boxes, known among the homeless as “box Hiltons,” make superb sleeping quarters.

We learn that not all homeless are panhandlers. At least some earn a living by “canning” .. collecting tin cans and redeeming them for cash. From what I could discern about the income generated by this activity, it pays better than my postdoc did, and of course, this is tax-free income, too.

Sometimes, it seems that Cadillac Man is a bit of a hero with impossibly noble ideals, such as the time when he stepped into a late-night fight to rescue a homeless stranger who was being beaten up by a group men. Interestingly, he later discovered that this “man” was not what he appeared to be. Instead, “he” was a “she” — a runaway teen-aged girl. Cadillac Man ends up taking care of this young woman, Penny, as if she was his daughter, introducing her to his circle of friends and teaching her how to survive on the streets. Later, they end up falling in love. Even though Penny is adamant about remaining on the streets with him, this spring-autumn romance ends after Cadillac Man secretly sets up a meeting at the Grand Central bus station between Penny and her aunt and sisters.

But why is Cadillac Man homeless? He doesn’t seem to be crazy or addicted to anything (except perhaps, to coffee). He teases his readers by peppering cryptic and leading comments throughout the early parts of his book, such as “I had a good life and I screwed up, plain and simple.” Only after the reader’s curiosity has reached a fever pitch does he finally share this particular story. Knowing this story makes me realize that it is nothing short of miraculous that there aren’t more people living on the streets, especially as the direct result of these current disastrous economic times combined with many people’s social isolation.

After I finished the book, I wrote the author with a few questions. He told me that he has not heard from Penny since the book had been published. He also told me that he has a home in Queens, and is in a stable long-term relationship, although he maintains close contact with his former street colleagues by visiting them frequently. Of course, this revelation raises more interesting questions, such as how did he get off the streets? It sounds as though a second book might be in Cadillac Man’s future.

Despite its rough prose, this readable and engrossing account of one man’s experiences on the streets of New York City is a must-read for politicians and public policymakers, those who work with the homeless and the impoverished, and also for anyone who is interested to learn about the lives and culture of “street people.”


NOTE: Originally published at scienceblogs.com on 12 April 2009.
Profile Image for Jenny.
3,364 reviews39 followers
April 3, 2010
A win from Goodreads
I gained compassion for those living on the streets, and you can kind of see how it happens. But I found this hard to read... lots of profanity and he had such a difficult life. I found parts really compelling, and other parts I could barely read.
Profile Image for Sarah.
385 reviews8 followers
May 13, 2015
If you've read my blog, you know how I came by this book. I live in Astoria, New York, and I'd been walking past a very friendly man for almost six months every day on my to the subway. I couldn't tell if he was homeless, though I did sort of think he was. When I finally stopped to speak with him, it was because I saw him writing. A few days later, he called me over and handed me his book.

Man, what a book. Cadillac warned me that it was written in "street", but I've read Pygmalion and Henry IV Part I. After an "ain't" in the first sentence, which I can't help but feel is there purely for shock factor, it's just like listening to him: great, deadpan sense of humor, natural language. It feels like having a conversation...well, with maybe more swears than he's used in my presence. For some reason people think that because I don't swear I'll be actively bothered if they do, which is not always the case. But I digress.

It starts rough, with a truly awful first Christmas on the streets of New York, and then both broadens to taken in the colorful individuals in Cadillac's life and narrows to focus on his past. I had a little difficulty following his timeline, but since he talks about how time means little when you don't follow the calendar, I wasn't terribly fussed--it was the sum total of the experience that mattered, not the order in which things happened.

Cadillac asked which parts interested me most. I said Irish and Penny (the latter seems to be everyone's favorite part), but I was also really interested in Chocolate Milk, Amber, and the other South Bronx prostitutes. Everyone Cadillac interacts with is met on their own terms, with the respect or contempt that they earn in his eyes. There's a very distinct moral code that he follows--this is a truly good man making his way in a very difficult world.

I told Cadillac it was sometimes hard for me to remember that the sometimes-violent version of him in the book is the same man who always greets me with a smile in the morning, though I know intellectually it's the truth.

I'm so, so thankful I had a chance to read this book. I've been volunteering at a soup kitchen for over a year now, and reading this book gave me a better appreciation of some of what our guests might be going through. Obviously Cadillac's experience is not representative of everyone's, or even most homeless people's, but that's kind of the point. There may be similar themes, but everyone has a different story of how they ended up where they are.

There's less concrete and literary criticism in here because I can't quite approach such a personal work in that way. Oh, sure, if this was in a literary writing workshop I could pick at the stitching and offer suggestions, but that's not why I'm reading this. I read this to learn more about a new friend than I ever have in one go.

I highly recommend this book to anyone who lives or wants to live in New York City. I'm guilty of looking away from the homeless on the street--I think almost all of us are--and I can't promise that I'm going to stop, but I'll definitely be thinking a lot every time I do it. There are so many stories, and we can't ever presume to know the "real" one that each person might have. I'm just grateful that Cadillac got to tell some parts of his.


Quote Roundup

Thar be swears ahead...

33) “You’re from Brooklyn, right?”
--“Yeah, how did you know?”
--“I recognize the accent.” The fucking accent, I mean.
I love Cadillac’s sense of humor, on text and in life! This line was especially great, though out of context it really doesn’t make much sense.

44) I bet if I walked in with no money saying I was hungry, they would have given me something. Unlike the yuppie restaurant that will chase you away, then afterwards any leftover food is dumped in the garbage. One day right in front of me and some of my people, an employee at one of those places deliberately dumped bleach over all the food in the dumpster, pouring slowly and watching our reaction. I wanted to bash that fucking smirk off his face, but that would have created problems for everyone so I did the next best thing. I started hanging out in view of the place. Picking my nose or scratching my balls in plain view of the customers, and others did the same.
Perfect revenge. What kind of sick freak does that to people? I’m actually reminded of something I saw in Stratford outside a 500-year-old house: it was a wooden cupboard the size of a microwave, with wooden slats spaced far enough apart that you could see inside. When I asked what it was, the curator said that the wealthy would put their leftovers out there each night for the poor. Is it so hard to do that little in this day and age?

60-61) In two years everything flipped over completely. I went from being the breadwinner to being at home with Jessie, and I resented it. I resented it. I wasn’t fulfilling my obligation as a husband and a father. The stay-at-home dad is just a recent thing: it was nonexistent back then.
This is why we need feminism, folks. While I can’t fault anyone for resenting unemployment, breadwinning shouldn’t societally be the obligation of the man in the house.

67) I could’ve called a friend, but I was just embarrassed. I took the attitude that whatever happens, happens. I guess I wanted to punish myself. For being a failure. For not trying hard enough to keep my family together. I didn’t care.
This from one of the nicest people I know…and in some very important ways, a very successful person, too.

94) Acting like sisters, [the prostitutes] talk about the johns and the tricks, their clothes, their dream of someday getting out of the profession. In reality most won’t, they just disappear. The lucky ones move on to another location, the unlucky you read about in the newspaper. The world’s oldest profession is also one of the world’s deadliest. The leading causes of death are pimps/boyfriends, johns, and in some instances other working girls. And suicide, the final act of desperation, which allows a girl to get out of this profession quickly.
I actually really liked this section. I was a little nervous to be reading about prostitutes from a man’s perspective, but Cadillac’s as even handed, kind, and no-nonsense with them as he is with everyone. Made it a bit easier to deal with hearing about the danger inherent in the line of work.

117) Unless she’s a big earner, losing a girl is no more than a minor annoyance. Sad but true, there are plenty more where she came from. They are everywhere--runaways, girls trying to make it as models, dancers, or actresses. The pimps wine them, dine them, then rape and beat them until they agree to work out of fear of dying. By then all hope for anything else is lost. Some get hooked on drugs and grow even more dependent.

140) So I thought, I’m going to be getting off the streets--[my brother’s] going to take me in, so maybe things will work out for me, maybe I’ve got a chance here. I stayed overnight, and the next day I was out canning and my sister came over to me and she says, you know something? You’ve got lice. Dan’s two daughters, they got lice. I said, I don’t have lice. But the street people, they’re stereotyped, so all right, I got lice. I had to go to her place, and she got this stuff from the drugstore, some crap to put in your hair. Whatever it was, it stunk like hell. Later on that day my brother came over and apologized, saying the kids got lice from some kids in school. So he told me I could go back to his place. I didn’t want to go back. I knew that if it wasn’t lice, it would be something else.

142) It hit me hard the first couple of months I was out there. Nobody was talking to me, I mean nobody. When you’re homeless, who would talk to you? People don’t even want to see you. So sometimes you may not realize it, you’d be talking out loud to nobody. You’re just getting it out of your system.
I used to hear a phrase to the effect that speaking to yourself was a sign of genius. Bit of a double standard there.

143-144) I felt so free, nobody riding my back, saying do this, do this, do that. I did whatever I wanted to do and I didn’t have to answer to anybody. I was free. I was free. You have so much freedom, so much time. Out in the streets I could basically come and go as I pleased. Like, today I’m going to be in Queens and tomorrow I’m going to be in Brooklyn, next day I’ll be in Staten Island. … When I was out there, I didn’t answer to anybody but myself. Not that I’m trying to glamorize homelessness, because it does have its bad points, but to me the beauty is there were no pressures.
As I think Cadillac says somewhere else in the book, you adapt. People always adapt. That said, I’m sure there are plenty of homeless people who would not agree. There are certainly restrictions, voluntary and societally imposed. And, of course, the lit student part of my brain demands to point out that the repetition of “I was free” could have just as much to do with convincing the narrator as the reader...though I’m obviously throwing “death of the author” out the window for this book.

152) After what happened with Harold, I said, I’m through. It seemed like everyone I ever got close to I lost. Same thing with the jobs, and after the garage closed, I said, that’s it, I don’t want to have another job again, never. I was terrified that it would happen again. After so many disappointments, how much can you take before you break? That’s it, I said, enough is enough. I can’t deal with this shit anymore.

206) It’s not rainwater falling from my eyes, it’s tears for a young woman with an awesome smile walking proudly wearing a garbage bag. Does that make any sense to you?
Yes, yes it does.

215) Sooner or later one of us will die, and I don’t want Penny to be alone out here.
Those who know me know I'm a cold-hearted crocodile, but Cadillac's selflessness really touched me. It's hard to get close to people, but letting them go is so much harder.

234) At some point we went past a large storefront window that caught my image passing and I had to step back to look again. Blue shirt, red tie, black pants, and green sneakers. Perfect. This is not me, an image of the life I once had and don’t wish to go back to. I lost everything, and to try again with the chance of failure, I won’t risk my sanity. The past is dead and my future is in God’s hands. Whatever he has in store for me, I accept willingly with open arms.

244-245) With Central Park back in the seventies and eighties, forget about it, your life wasn’t worth a nickel if you went through there after dark. Now it’s like Little House on the Prairie over there. But still a lot of people won’t go in there at night, so that’s a plus for the street people because they know they won’t be hassled by one of the outsiders going jogging.
I was actually just talking about the relative safety of Central Park these days.

248) People beat on the homeless because they can get away with it. We got mental problems, right, s they say. People are malicious. That’s their mental problem. To let their frustrations out they’re going to pick on somebody like me.
It’s amazing how many sickos there are among the “normal” people in this world.

270) Politicians claim they will make the shelters safer by adding more security. What good would that do with the lights off? Security is no good to us, staying in their warm, cozy office while someone is being robbed, beaten, or worse in front of the place. Why do you think some of us go into hiding and take our chances with Jack Frost?
There were a few truly horrifying things in this book, and this was one of them. I never knew just how bad the shelters could be—I’ll never why people don’t go to them again.
Profile Image for Ellen Morris Prewitt.
Author 8 books8 followers
November 12, 2018
This memoir of living on the streets has humor and bravado and the bonds of community that form on the street, and (often questionable) survival tactics. And, every so often, tucked inside all of this spectacle, are one-line sentences acknowledging how emotionally difficult it all is. These quiet lines reflect the title, "Land of the Lost Souls." Several times, Cadillac Man mentions those who are no longer on the street, and the wishful thinking that they have returned to family or gone onto better situations ("We all wish for it, and a few are lucky to be accepted back to the family fold.") But the truth is, they have died. Living on the streets is tough and terrible (for 8 yrs, I facilitated a weekly writing group of men and women who were experiencing homelessness, with hundreds of writers joining us over the years, which culminated in the group's memoir Writing Our Way Home: A GroupJourney Out of Homelessness). Land of the Lost Souls' good writing and jokes and startling details can overpower these moments of poignancy, but, for me, they are the moments of the most honesty and vulnerability.
Profile Image for Fortunato.
76 reviews
August 12, 2025
it's an alright book. for those unaware of the issues faced daily by the homeless and the cycle they can find themselves trapped in, it will be eye opening. it's entertaining but the guy definitely gives the impression he's embellishing and a lot. though to be fair, the introduction says he'll lie occasionally. but then later "word is bond." so take what you will from it, but it's still a good read
Profile Image for kris.
3 reviews
September 1, 2023
When I first read this book I was in high school but it was only certain chapters but as an adult I read the whole book and I really enjoyed the whole story. I enjoyed how Cadillac man put his whole heart and soul into is life story into a book. And how it was in the street of New York
Profile Image for Becky.
563 reviews
August 16, 2023
Raw, real, intriguing, funny, sad. Definitely worth the read.
Profile Image for Joel.
196 reviews8 followers
April 27, 2009
This is a must read. I wish there were more stars than 5 to give this book. The author, a homeless man, who, like many of his friends in the book, was not always homeless. The author, Cadillac Man, does a stunning job at taking the reader from his/her location and transports them to NYC, NY where he is homeless. The pages are filled with rude, crude, lude, even nude stories that are real, or so he says. There is love like you've never seen, heart ache and break like you've only imagined or maybe have seen in a movie, there is triumph and defeat. Cadillac Man takes you into the real life and lives of the homeless, from a boots-on-the-ground perspective that as far as I know is unrivaled. The prose with which he writes is honest, open, gritty, and grainy. It's not polished and pretty, it's raw, painfully raw. The emotions bleed on every page. If you want to know what it is to give when you have nothing, to help others when others should be helping you, to be happy under any circumstance, to really love someone, then this is a book you cannot pass up. It is not only a character study but it is informative, to the point of being a guidebook should you ever find yourself homeless. It is a mini-ethnography on homelessness. It is so much wrapped up into one scrumptious literary morsel. You have to read it.
Profile Image for Mike.
42 reviews1 follower
May 4, 2010
I really liked almost everything about this book from start to finish. The only downfall was when Cadillac Man continuously used the phrase "word is bond", it made me angry actually, that is how much I hate that phrase. The rest of the book was really written really well. The way the story was told made me feel as if I was conducting an interview with the author. The pace of the story moved well and had many interesting sidebars that shed light on some of the peculiar behaviors of homeless people I have previously seen. I definitely have a different outlook as to the way I consider a homeless person's situation. I wish more people were as kind and good hearted as Cadillac Man. The life of this man was at one time very difficult, I hope because of this book he made enough money to enjoy a more comfortable existence.
Profile Image for Rita.
17 reviews
September 12, 2015
Life on the streets of New York

Writing keep me interested. Initially was suspicious re actual existence and many strength of social supports reported among street people. Have never noticed them talking to each other. Distrust Cadillac mans self portrait as a person of strong values, a sort or robin hood of the streets. Also find questionable his allegations of all the stuff he carries on his cart for hygiene and wound care from baby wipes to peroxide; dressings + antibiotic ointment . Also living in NYC have never noted a street person too proud to accept $ handouts. Difficult to feel any sympathy given that he seems to present his life as now chosen and much preferred rather than a low paying job where he would be expected to be accountable for his time.
19 reviews1 follower
March 31, 2018
One of the best books I've ever read. Cadillac Man's jumpy writing style suites me perfectly. Imperfect grammar and punctuation, but only when it assists to get his point across more fully.

The lines between suicide and indifference blend so thoroughly in him that his simple habit is to not look both ways crossing the streets of New York. As a younger man, his wife and child disowned him, and his urge to live hovers just above the bottom of the barrel.

Well written, with many insights into the life of the depressed and homeless (example: Don't EVER go to a NY homeless shelter at night). There is no one I couldn't recommend this book to.
Profile Image for Deodand.
1,299 reviews23 followers
April 9, 2010
I'd read Cadillac Man's Esquire dispatches, so I knew to expect something good. (Say what you will about men's mags, overall I find the reportage is much higher in quality.) I really like his prose style - I'm a sucker for something simple. Cadillac Man pulls us into his world very effectively.

Naturally you will find that Cadillac Man is the hero of his own stories, but that's OK with me. He doesn't waste time painting pictures or putting much context on the situations, he just tells the story. It's probably a bit like listening to the man speak about his life.
Profile Image for Liz.
399 reviews4 followers
October 2, 2010
What a great book! Cadillac Man tells about his life on the streets in Manhattan and how you survive on the streets. He writes about how he got on the streets with his failed marriage and his wife's expectations. He tells about how to can and all the friends he meets on the streets. He tells about the struggles and how bad the shelters are. He even meets someone he falls in love with that could be his daughter. He helps Penny (who is a teenage runaway) get back to a family that loves her. It is a very moving memoir!
Profile Image for Joe.
51 reviews8 followers
June 14, 2011
I wouldn't say this is the most entertaining of reads, but it's an extremely insightful book about the homeless written by someone who's been living on the street for 15+ years if I remember correctly. Because it is essentially just a collection of stories about street life gathered from the journals of Cadillac Man, you can't go into this expecting the most grammatically-correct book or very sophisticated story telling. However, you CAN expect authenticity and very interesting anecdotes from someone who chose to live an unorthodox life.
Profile Image for Jamie.
92 reviews6 followers
September 4, 2010
Pithy and honest, this book is one of the best memoirs I have ever read. Many of the situations and aspects of homeless life are opened up for us to see accurately, and I was consistently surprised by my own ignorance of the reality and the incorrectness of my impressions. Even if you don't particularly villainize or victimize the homeless, even if you simply accept them how they are and have compassion for them, this book makes it very clear that an "outsider" can't understand what street people live through. But this book educates by beginning to break down that wall.
Profile Image for Glenda.
155 reviews15 followers
April 30, 2018
Cadillac Man's stories of his life on the streets need no embellishments or exaggerations. He narrates with a stripped down view of the world around him, showing the stark realities of homeless life, some tragic and some entertaining. He shows the reader that not all homeless fit the stereotypical "drugged-out, alcoholic psychopath" mold. The people who wander in and out of the narrative evoke empathy and provide humor and tragedy. A fascinating read.

Librarything giveaway and review 4/5/2010
Profile Image for Lenny.
5 reviews1 follower
August 18, 2012
Wow, this one just floored me. The true story of life on the streets for a man who's been homeless in New York City for many, many years. So he's not the best writer and likes to make cheesy jokes...didn't matter, his tale was enthralling. Maybe it's just because I spend so much time in NYC, maybe it's because I've always wondered how the homeless survive. This was a funny, touching story that often left me cringing....you can't help but feel like you're in his shoes. Well worth it, and a pretty quick read.
Profile Image for justablondemoment.
372 reviews7 followers
August 25, 2017
This was a very honest no bull book on what living on the streets is like. Hard to follow at times as the chapters which are each different stories jump around.

My heart breaks for the children out there as they to me are the innocent and most have tear-producing stories, of HOW they came to be there, just as with the girl, Penny in Cadillac Man's life.

I must admit; it is harder for me to give sympathy to the older street people, but this book changed me some making me think of things I hadn't taken into consideration before. Overall, well worth the read.
Profile Image for Kristy.
639 reviews
April 16, 2010
Cadillac Man has been homeless on the streets of New York City for 13 years, and this memoir was distilled from his journals. He goes back and forth between vignettes of his life as a homeless man and the story of how he got where he is today. The narrative is interesting and moving, and his personality bursts through every page of the book. The dialogue is a little goofy, but fits with the book and the storytelling/journaling style. Definitely worth a read.
120 reviews1 follower
May 21, 2010
A fantastic look into homelessness in NYC and, more specifically, into the life of Cadillac Man, a man who's been on the streets over sixteen years. Cadillac Man tells the story of how he ended up on the streets of New York and what living in the streets entails. The good, the bad, the heart-warming and the heart-breaking. There's no sugar-coating here. A wonderful read and one that just may change the way you view homeless people.
Profile Image for Robyn Obermeyer.
556 reviews47 followers
December 8, 2014
this book was very interesting, I liked the way the guy describes life on the streets> Canning and fighting and watching out for each other and making coffee on the street, what he gets by on, how he describes liking being cold out and noone bothering him putting down traps around himself before sleeping. All very real stories that definitely give valuable insight into the homelessness in New York city!
Profile Image for Amy.
244 reviews2 followers
March 13, 2010
I got this book as part of Goodreads First Reads. I enjoyed it because it painted the men and women who live on the streets in a different light. Cadillac Man explained the lives of the homeless in a matter of fact way, and he was endearing.

It also made clear that our current solutions for ridding ourselves of the homeless problem are not working.
Profile Image for Jennifer.
434 reviews3 followers
October 26, 2009
This was interesting book that provided a brutally honest portrayal of what life is like for the homeless. It addressed some of the stereotypes that society holds about the homeless population, while being honest with the reader about things like safety, violence, health, and welfare.
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