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Crooked Smile: What It Took to Escape a Decade of Homelessness, Addiction, & Crime
Featured in the
Wall Street Journal
Crooked Smile details one man's journey that left him homeless on Skid Row, and what it took to escape a decade of addiction.
"Darkly humorous" is an understatement when it comes to this tale of addiction, homelessness, incarceration, and redemption. Jared Klickstein, the child of two heroin addicts who eventually became addicted himself, takes listeners on a raw and personal journey from his unsettling and secretive childhood in the suburbs to the slums of Skid Row. Through tales of violence, relapse, and deep inner struggle, Klickstein provides a harrowing account of his personal encounter with near-death.
But this story is not just about one man's life—it's about the hundreds of thousands of homeless and drug-addicted Americans who are on the streets right now. It's about those who need help the most, and what can be done to address the growing addiction and homelessness problems. Klickstein offers a fresh take and solutions to both epidemics, providing firsthand experience and insight into what policies should be put in place to mitigate the suffering. Crooked Smile recounts one man's escape from a hellish life—and carves a valuable path for others.
Crooked Smile details one man's journey that left him homeless on Skid Row, and what it took to escape a decade of addiction.
"Darkly humorous" is an understatement when it comes to this tale of addiction, homelessness, incarceration, and redemption. Jared Klickstein, the child of two heroin addicts who eventually became addicted himself, takes listeners on a raw and personal journey from his unsettling and secretive childhood in the suburbs to the slums of Skid Row. Through tales of violence, relapse, and deep inner struggle, Klickstein provides a harrowing account of his personal encounter with near-death.
But this story is not just about one man's life—it's about the hundreds of thousands of homeless and drug-addicted Americans who are on the streets right now. It's about those who need help the most, and what can be done to address the growing addiction and homelessness problems. Klickstein offers a fresh take and solutions to both epidemics, providing firsthand experience and insight into what policies should be put in place to mitigate the suffering. Crooked Smile recounts one man's escape from a hellish life—and carves a valuable path for others.
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Published February 25, 2025
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Displaying 1 - 30 of 55 reviews
September 7, 2024
This book is amazing and every American should read it for insight into the addiction epidemic. Thank you Matt McCusker for the recommendation!
July 26, 2024
The most important voice concerning homelessness and addiction is probably an ex-homeless addict. Raw, funny, well-written, and full of actual ideas and refreshing optimism. Check out my conversation with the author here: https://www.patreon.com/posts/crooked...
December 14, 2024
klickstein’s words were a breath of fresh air that everyone needs to inhale. unapologetically written, funny, and insightful, crooked smile drives home the intersectionality between addiction, homelessness, and crime through klickstein’s lived experiences. it’s firsthand accounts like this that should be informing decisions makers on approaches to long term change.
i heard about this book through my boyfriend, who generously let me take his copy of crooked smile on a plane back to new zealand. so if jared ever sees this - hello from the southern hemisphere!
i heard about this book through my boyfriend, who generously let me take his copy of crooked smile on a plane back to new zealand. so if jared ever sees this - hello from the southern hemisphere!
August 22, 2024
“I’m sure if we refrain from funding a proxy war in the next ten years, we could afford to help these people [addicts] for the next century.”
I heard about this book from Shane Gillis and Matt McCuskers podcast.
Such an insane story to read. Jared’s firsthand perspective on how to combat the addiction epidemic in this country was very insightful, and should be taken seriously by policymakers.
I heard about this book from Shane Gillis and Matt McCuskers podcast.
Such an insane story to read. Jared’s firsthand perspective on how to combat the addiction epidemic in this country was very insightful, and should be taken seriously by policymakers.
February 21, 2025
5 ++ stars. Excellent. A terrifying and devastating insight into addiction. This is the tale of an addict from Skidrow to San Francisco, back to Skidrow. This guy has seen it all, done it all and best believe, it is nightmarish.
The level of storytelling and the raw humour in places it had no business being, made this book a stand out addiction memoir, and a stand out book overall. The author may as well have been in front of you, beer in hand, regaling a crazy night he’d had. It reminded me in many ways of Wild by Cheryl Strayed (one of my favourite books). People with a wild story to tell and the ability to tell it in its entirety, with a soul level honesty that lets the story speak for itself. The author did not spare himself any little indignity. There is a depth and authenticity that is compelling to read. I got something from this book that I had been looking for, something that doesn’t come around too often.
The author possesses such incredible insight and his experiences and opinions were enlightening. I ended this book with goosebumps.
Thanks to Netgalley for the arc. I wish the author every success with this book.
The level of storytelling and the raw humour in places it had no business being, made this book a stand out addiction memoir, and a stand out book overall. The author may as well have been in front of you, beer in hand, regaling a crazy night he’d had. It reminded me in many ways of Wild by Cheryl Strayed (one of my favourite books). People with a wild story to tell and the ability to tell it in its entirety, with a soul level honesty that lets the story speak for itself. The author did not spare himself any little indignity. There is a depth and authenticity that is compelling to read. I got something from this book that I had been looking for, something that doesn’t come around too often.
The author possesses such incredible insight and his experiences and opinions were enlightening. I ended this book with goosebumps.
Thanks to Netgalley for the arc. I wish the author every success with this book.
October 18, 2024
It’s not an easy read, it's heart-wrenching, it is too long, never ending suffering, worse and worse. If Jared didn't write with such self-irony and humor I probably could not have finished this book. But it's so important not to talk about addicts but to hear them, to get their point of view.
A book for people who are close to an addict, for addicts to see that there's always a chance to turn your life around, and for politicians who have the means to change the way we as society confront the problem.
What Jared proposes is probably the best possible way to react to a crisis that only gets bigger and bigger.
A book for people who are close to an addict, for addicts to see that there's always a chance to turn your life around, and for politicians who have the means to change the way we as society confront the problem.
What Jared proposes is probably the best possible way to react to a crisis that only gets bigger and bigger.
November 12, 2025
An addict’s memoir/message about how we should mandate rehab vs handing out free needles. How briefly jailing and forcing him into sober living made him turn his life around, knowing how enabled he was by himself, people in his life pre- and post-homeless. He asserts this issue doesn’t fall into any politically convenient party answer as everyone’s out to make a buck, taking the word of “expert”s (FDA says Oxy is non-habit forming) or soft do-gooders or not realizing how the problem starts so young and even when it seems addressed properly, it takes many tries to get clean and even rehabs or asylums over-medicate people to keep them less annoying.
Heard this guy on Matt & Shane’s Secret Pod, wish he read it himself though this Audible narrator isn’t bad. Smoking crack on Skid Row was his bag but he’s been to all the major cities, doing heroin and meth. It was there he’d see people kill and rape each other without consequence the most as cops kept away. Lot at first is Cali stats on corruption of allegedly well-meaning systems.
His parents, Eastern Bloc Jew blue-collar, were addicted to heroin and there’s a second semi secret fam drama, making him feel more attention-starved. Some extended fam got addicted while fighting in Vietnam. His mom ODs maybe intentionally when he’s in high school, claims raped at 8, so self-medicates until schitzo. Dad started using at 13 and used functionally for a surprising amount of yrs. He wanted his son to go to college and that’s part of why he sold drugs but soon just did the drugs himself.
It’s ironic he thinks his once-loving parents were just emaciated stoners always involved in fender benders. The paranoid dad would screw and unscrew his boarded basement door every day. The kid gets dozens of pets like Guinea pigs, using their guilt against them. Feeding into their psychosis, guarding perimeters armed. He thinks he’ll never be like them but wants to escape, going to parties, drinking, smoking, and doing pills he assumes must be far safer as they come from drs who easily give out.
“Nothing’s slower than a tweaker in a hurry.” Sayings like that and some knack for writing and callback clarifications or foreshadowing make this voice truly unique without being loud.
He goes to the Occupy Wall Street protests after becoming a wastoid at college, finding this a good place to tent and cop good meth. He steals delivery bikes, sells fake drugs on Craigslist (Ibuprofen, sleep aids), gets tens of thousands of dollars worth of medical treatment for free on his constant infections and “lasagna feet.” He lies to himself uppers are fine compare to h, becomes a ride-along often of dealers to sustain his habit.
I’m surprised so many are willing to share their drugs, but they’re lonely and need a friend like the author. What started the spiral to begin with for everyone. He gets help from friends and rich fam “to kick” at many stages. Including a Christian dude who was in same boat on Xmas. Glad he’s aware how much he screwed up and took advantage of people so selfishly/spoiled over and over. Cushy rehabs and meals and care normal people would have to pay so much for or never experience even if they did everything right and never got on drugs.
At the worst points in his addiction, after many golden opportunities to quit, he links up with a fellow methhead paranoid he stole her phone, so she ties him up naked, stuffs in a suitcase, and gets friends to threaten to human traffic him. Wiggling out of that with talk of cops and news stories, he continues to buy drugs. His dealers even have their tiny kids sell for them!
Once he’s finally jailed (he’s busted like three times but just in and out w/ crazy legal leniency), he has to hide he’s Jewish among white supremacists. Since it’s de facto to join, they’re weirdly affectionate but all rules that say you can still be friendly with other races but not too much cuz they don’t want race riot to break out as an excuse when one person does something wrong.
There’s also rules about beating people if they’re not hygienic enough. So funny the swastika guys are like “Hey, calm down about that race shit” and turn out not to be “half-breeds” of whatever and even happy their friend comes out so they can eat his kosher meatballs. He sells such to make money there. It’s not the 10k he could pull easy scheming on streets for dope money, but jobs give him purpose anywhere. Make him less suicidal like writing this book and getting clean with connections w/ sober people.
Heard this guy on Matt & Shane’s Secret Pod, wish he read it himself though this Audible narrator isn’t bad. Smoking crack on Skid Row was his bag but he’s been to all the major cities, doing heroin and meth. It was there he’d see people kill and rape each other without consequence the most as cops kept away. Lot at first is Cali stats on corruption of allegedly well-meaning systems.
His parents, Eastern Bloc Jew blue-collar, were addicted to heroin and there’s a second semi secret fam drama, making him feel more attention-starved. Some extended fam got addicted while fighting in Vietnam. His mom ODs maybe intentionally when he’s in high school, claims raped at 8, so self-medicates until schitzo. Dad started using at 13 and used functionally for a surprising amount of yrs. He wanted his son to go to college and that’s part of why he sold drugs but soon just did the drugs himself.
It’s ironic he thinks his once-loving parents were just emaciated stoners always involved in fender benders. The paranoid dad would screw and unscrew his boarded basement door every day. The kid gets dozens of pets like Guinea pigs, using their guilt against them. Feeding into their psychosis, guarding perimeters armed. He thinks he’ll never be like them but wants to escape, going to parties, drinking, smoking, and doing pills he assumes must be far safer as they come from drs who easily give out.
“Nothing’s slower than a tweaker in a hurry.” Sayings like that and some knack for writing and callback clarifications or foreshadowing make this voice truly unique without being loud.
He goes to the Occupy Wall Street protests after becoming a wastoid at college, finding this a good place to tent and cop good meth. He steals delivery bikes, sells fake drugs on Craigslist (Ibuprofen, sleep aids), gets tens of thousands of dollars worth of medical treatment for free on his constant infections and “lasagna feet.” He lies to himself uppers are fine compare to h, becomes a ride-along often of dealers to sustain his habit.
I’m surprised so many are willing to share their drugs, but they’re lonely and need a friend like the author. What started the spiral to begin with for everyone. He gets help from friends and rich fam “to kick” at many stages. Including a Christian dude who was in same boat on Xmas. Glad he’s aware how much he screwed up and took advantage of people so selfishly/spoiled over and over. Cushy rehabs and meals and care normal people would have to pay so much for or never experience even if they did everything right and never got on drugs.
At the worst points in his addiction, after many golden opportunities to quit, he links up with a fellow methhead paranoid he stole her phone, so she ties him up naked, stuffs in a suitcase, and gets friends to threaten to human traffic him. Wiggling out of that with talk of cops and news stories, he continues to buy drugs. His dealers even have their tiny kids sell for them!
Once he’s finally jailed (he’s busted like three times but just in and out w/ crazy legal leniency), he has to hide he’s Jewish among white supremacists. Since it’s de facto to join, they’re weirdly affectionate but all rules that say you can still be friendly with other races but not too much cuz they don’t want race riot to break out as an excuse when one person does something wrong.
There’s also rules about beating people if they’re not hygienic enough. So funny the swastika guys are like “Hey, calm down about that race shit” and turn out not to be “half-breeds” of whatever and even happy their friend comes out so they can eat his kosher meatballs. He sells such to make money there. It’s not the 10k he could pull easy scheming on streets for dope money, but jobs give him purpose anywhere. Make him less suicidal like writing this book and getting clean with connections w/ sober people.
January 11, 2025
An enthralling, disturbing, and funny read. I'm just happy that Jared made it out of the shit.
March 22, 2025
This was actually so interesting to read about Jared’s life of drug abuse and homelessness. It’s honestly impressive to me that he remembers as much as he did to write this book.
September 10, 2024
I really enjoyed this book. Been awhile since I started a book and couldn’t put it down. It’s well written and keeps you wanting to read on and learn about Jared’s story. Couldn’t recommend more.
October 20, 2024
Amazing and unbelievable story. Starts such an important conversation about homelessness and addiction in our country.
May 11, 2025
With Alberta facing “Compassionate Intervention” otherwise known as mandatory treatment for addiction, this is a very timely book! Having worked in addiction and mental health for the last 12 years I have some very strong views on mandatory treatment for addiction. Evidence shows it doesn’t work long term. I’m thrilled it finally worked for Jared. But his path is not the only one.
Going into a book where you already have your mind made up, may have made me a bit jaded by the forward that said mandatory treatment must be used. But as I listened to Jared’s story I thought….who am I to judge? Each person has their own journey and whatever worked for Jared worked for Jared. What I didn’t like was Jared’s premise that if it worked for him it would work for everyone. I also disagree with his conclusion that it was mandatory treatment that got him clean. I believe it was the community he built while in mandatory treatment. It is that human connection and feeling of worth that breaks the addiction cycle.
The best part of the book was the ending where Jared supplied ideas for change. The after care ideas of work programs for retraining and stable housing are awesome!
Overall I really enjoyed the writing and the story and this book might have changed my mind slightly about the evils of Compassionate Intervention. We currently have LONG wait lists to get into voluntary treatment and then once a client is finished, there is little after care.
Highly recommend reading this.
Going into a book where you already have your mind made up, may have made me a bit jaded by the forward that said mandatory treatment must be used. But as I listened to Jared’s story I thought….who am I to judge? Each person has their own journey and whatever worked for Jared worked for Jared. What I didn’t like was Jared’s premise that if it worked for him it would work for everyone. I also disagree with his conclusion that it was mandatory treatment that got him clean. I believe it was the community he built while in mandatory treatment. It is that human connection and feeling of worth that breaks the addiction cycle.
The best part of the book was the ending where Jared supplied ideas for change. The after care ideas of work programs for retraining and stable housing are awesome!
Overall I really enjoyed the writing and the story and this book might have changed my mind slightly about the evils of Compassionate Intervention. We currently have LONG wait lists to get into voluntary treatment and then once a client is finished, there is little after care.
Highly recommend reading this.
August 25, 2024
Even apart from the harrowing stories of his time on skid row, Jared pens some of the best descriptions of the Mental side of addiction that I've ever read. Also he rules and is The Man. I spoke to him about his experience with manual labour and its role in his recovery on the NICE podcast, which can he listened to here: https://open.spotify.com/episode/3Nnp...
March 13, 2025
Klickstein’s story reveals how Anglo-Protestant hyper-individualistic social conditioning reinforces the belief that mental illness and addiction are the result of personal failings, further entrenching people in their lack of self worth. Klickstein’s commentary on the wellness industry and public policy with the purpose of reversing these societal woes are fundamentally flawed as they consistently have the underlying goal of profit maximization and convenience, showing how neo-liberal policies and strategy are inherently unpragmatic and do not seek to tackle the root causes of societal troubles. Klickstein’s emphasis on the need for community and hope, underlines two fundamental aspects of the human experience that make rehabilitation and reintegration into society possible; deep connection and support to those around you and the ability to make small incremental steps towards a higher purpose.
March 1, 2025
It is funny at times. It is maddening at times. It is an incredible story throughout.
March 19, 2025
I love this book, so much
May 30, 2025
Crooked Smile won’t win any prizes for writing, it doesn’t need to. A harrowing, funny, and bizarre look into the life of a modern addict. The book left me feeling troubled and a little ashamed about the way our nation handles drug addiction.
It also helped me understand the mind of an addict and see similar tendencies in myself and others. The copious excuses people use to maintain their status as righteous (or at least the victim of circumstance) can be just as devastating when applied to work, love, or status seeking.
Complete and utter freedom, the kind of freedom that can only exist without ties to any person or place, leads to selfish, carnal fulfillment and eventual self destruction.
It also helped me understand the mind of an addict and see similar tendencies in myself and others. The copious excuses people use to maintain their status as righteous (or at least the victim of circumstance) can be just as devastating when applied to work, love, or status seeking.
Complete and utter freedom, the kind of freedom that can only exist without ties to any person or place, leads to selfish, carnal fulfillment and eventual self destruction.
October 2, 2024
I have been longing for this book ,even though I didn’t realize it, ever since I saw a crackhead for the first time. Finally I get some insight into how these guys operate. Crafty fellows. I love them.
December 4, 2025
Jared has excellent insight into how to approach our addiction crisis. I hope he continues to advocate and becomes a leader in our struggle to mend society.
January 9, 2025
One of the funniest and intense books I have ever read. Couldn’t put it down.
December 5, 2024
Excellent! Riveting stories, interesting perspectives on addiction and overall uplifting
January 1, 2025
Amazing book!!! I can’t recommend this enough, Jared did a fantastic job telling the narrative of his journey with drugs. Huge thank you to Matt McCusker for the recommendation.
December 27, 2024
Were your parents heroin addicts? Mine neither, but Jared’s were. This autobiographical tale of a life dominated by elicit drugs will change the way you think about addiction, homelessness, and the current efforts put forth to stop both. It is the only biography that has made me laugh, tear up, and literally squirm with discomfort. I would recommended this book to anyone who is curious on how to curb the homeless/drug issues that plague modern America.
November 11, 2025
Definitely recommend it!!!
I absolutely loved this book, I can't recommend it enough I honestly
think that everyone should read it
It is very well written
I absolutely loved this book, I can't recommend it enough I honestly
think that everyone should read it
It is very well written
November 7, 2024
Genuinely one of the most raw, insightful books I have ever read. I learned so much about a part of the human experience I am in some ways so far removed from, but in other ways is right in front of me every single day.
I would strongly recommend this book to anyone looking to truly understand the state of the drug addiction and homelessness crises in America. But I’d also recommend it to anyone struggling with either/both of those challenges themselves. I’m planning to donate my copy to a place where it can be used as a resource, and I’d encourage anyone who reads it to consider doing the same.
I would strongly recommend this book to anyone looking to truly understand the state of the drug addiction and homelessness crises in America. But I’d also recommend it to anyone struggling with either/both of those challenges themselves. I’m planning to donate my copy to a place where it can be used as a resource, and I’d encourage anyone who reads it to consider doing the same.
November 6, 2024
Well if you want to read about someone spiraling many times into drug addiction hell - this books for you. This book did give me more insight into the mind of a drug addiction and was as interesting as it was depressing. It also gave me something to think about on how are society deals with addicts which isn’t something I really thought about. Maybe over compassion is not good.
October 23, 2025
devastating, humanizing, and insightful. this author’s reflection of his own descent into drug addiction and homelessness is one i would recommend to anyone looking to expand their knowledge of the drug epidemic from someone who lived it first hand!
January 28, 2025
Jared takes you on a journey through his crazy life of addiction to just about every drug under the sun. His prose is direct, deeply reflective, highly self-aware, and has no trace of the usual cliches of blame and self-pity. From getting stuffed into a suitcase by a group of methed out ladies to being the most popular guy in prison because of his Jewish diet, Jared really lays it all out there.
This entire review has been hidden because of spoilers.
October 8, 2024
Spectacular writing and storytelling. All I could’ve asked for was more stories but that’s just me being greedy. Thoroughly enjoyed from start to finish, and has caused me to think deeper about the state of addiction treatment. Highly recommend!!
March 20, 2025
Legitimately an incredible read. Very thought-provoking commentary between the absurd/darkly humorous stories in this book. This really opened my eyes to a world that I have only experienced from a very outside perspective, but have no first-hand experience with.
Displaying 1 - 30 of 55 reviews