To say Moshe Kasher had a tumultuous upbringing would be an understatement at best. The 32-year-old comedian and author now appears regularly on E!'s Chelsea Lately and his clean-cut look — slicked-back hair with thick black glasses — appears to dispel the notion of any momentous regrets. But Kasher in the Rye, his compelling memoir of a rough-and-tumble childhood with two deaf parents and a festering substance-abuse problem, isn't exactly easy to stomach.

Written in Kasher's distinctly witty and often frantic narrative voice, the book takes you on a journey through his stints in rehab, jail and therapy as a teenager. It's not so much a redemption story as it is a comical reflection on a past life, one that Kasher left behind after getting sober at 16. “When I was about to turn 30, I had a realization that I had this full measure of life between that insane period and where I'm at now,” he explained recently in an interview at the vegan restaurant Flore in Silver Lake.

Kasher's parents split up when he was 9 and his mother whisked him and his older brother away to Oakland, where they lived mostly on disability assistance and food stamps. In the book, he tells of his parents' romantic first encounter, at the World Games for the Deaf in 1967, but his father, a painter before rededicating himself to Hassidic Judaism, often flew into uncontrollable fits of rage, once breaking his mother's fingers. “Seems like my dad might've been born angry too,” he writes in the first chapter.

Later, Kasher would spend summers in Brooklyn with his father, awkwardly trying to fit in with ultra-Orthodox children his own age. Back in Oakland, humor came in handy when he started hanging out with “the fuckups” in middle school, seeking out a sense of family. “I always found myself in this abnormal middle space, and when I found these other kids that seemed to live in that middle space too, then we just found a little groove,” a groove that included robbing rich kids for their weed, stealing his mother's car and being falsely implicated in a gang rape.

See Kasher's appearance on Conan, above

After getting kicked out of four different high schools and enduring numerous therapy and treatment programs foisted upon him by his mother, Kasher took it on himself to finally clean up. “It was kind of an awakening rather than a particular event,” he says, quick to deny the “rock-bottom” cliché. “This idea of a guy waking up in a hotel room with $60,000 and a dead hooker. It's exciting, but it's not as scary as the idea of having a thousand degrading moments and not realizing it until you've been in this grind for months.”

Kasher earned his G.E.D. at age 16 and later became a sign-language interpreter, sitting in on the same family therapy sessions he had attended in the years prior. Still staying sober, he surprisingly found his next social niche in the company of ravers at local warehouse parties. Raves offered him a “second childhood” and the kind of loving social group he had never experienced, though he's the first to admit most of it was chemically induced.

On a recent episode of the You Made It Weird podcast, Kasher told fellow comedian Pete Holmes about the first rave he went to, when he stashed a heavy bottle of cologne in a sock in his backpack to use as a weapon in case a fight broke out. Though six months sober at the time, he obviously had yet to shed his rough exterior. “I was violent. I was sexist. I was a pig,” he said. But by the end of the night, Kasher explained how he “melted, as this violent, awful kid and slowly became this soft guy.”

The story is part of a strong musical influence in Kasher's life, beginning during his childhood when he and his brother would blast gangster rap in the car, while their mother drove along, unaware of the misogynistic lyrical stylings of Too Short and Snoop Dogg. As a dedication to the heavy influence of gangster rap during his adolescence, each chapter of Kasher in the Rye is titled after a different rap song from the early '90s.

Another Kasher stand-up bit, in the video above

Kasher jokingly claims that he and longtime friend and comedian Chelsea Peretti were the “original wiggers” (a term for a white person who emulates African-American culture in some way). The two met in junior high and, as two of the only white kids in their school, became fast friends; they remain close to this day. In fact, Peretti was the person who first inspired Kasher to try stand-up comedy. Before graduating with a religious studies degree from UC Santa Barbara, he attended community college in the Bay Area, where he studied theater and wrote several long-form monologues.

On a trip to New York, he saw Peretti perform her stand-up routine and reacted viscerally. “I thought, this is like the perfect mixture of the two things I love, performing and writing your own stuff,” Kasher explained. He returned to the Bay Area and began performing in small rooms around San Francisco, leaning toward more subversive influences, such as well-known pot comic Arj Barker, absurdist W. Kamau Bell and new Daily Show correspondent Al Madrigal. In Los Angeles, he's found a home at alternative venues like UCB and Largo at the Coronet.

The uniquely sly and sarcastic wit of Bay Area culture is still an integral part of Kasher's comedic style. In his act, he deftly broaches heavy subjects like sex and religion, often dropping several punchlines within the same joke. And though the subject matter of his book is also quite heavy at times, Kasher is one of the few comedians able to effectively mirror his comedic tone and sensibility in writing. “The first note my editor gave me was 'less jokes,'” he says of the writing process. “I had to kind of purge all of these things that were distracting from the narrative.”

When he isn't doing stand-up or readings to promote the book, Kasher hosts a weekly podcast called The Champs with Chappelle's Show co-creator Neil Brennan and comedian DJ Douggpound. He's also toying around with the idea of turning Kasher In the Rye into a one-man show, along the lines of comedian Mike Birbiglia's Sleepwalk With Me, which was featured on This American Life and recently made into a movie. When asked what his story would look like on the big screen, Kasher replies casually, “It'd be like The Wonder Years, but a lot darker.”

Kasher in the Rye: The True Tale of a White Boy From Oakland Who Became a Drug Addict, Criminal, Mental Patient, and Then Turned 16 is available now from Grand Central Publishing.

Follow us on Twitter @LAWeeklyArts, Aaron Frank @franknbeats and like us on Facebook.

Advertising disclosure: We may receive compensation for some of the links in our stories. Thank you for supporting LA Weekly and our advertisers.