IN MANY WAYS, Freddy Negrete’s life is the life of Los Angeles. It is a life lived out on the edge, mapping the fringes of the city’s experience, showcasing the dramatic contours of the Wild West. It traces the story of a throbbing postwar Los Angeles sprawl, but also unpacks the unique drama of Negrete himself, the gangbanger-turned-artist.

Negrete possesses near rock-star status in the tattoo art world. Today one might catch a casual glimpse of him at his West Hollywood parlor, Mark Mahoney’s Shamrock Social Club Tattoo (a block west of Book Soup), but don’t bother trying to introduce yourself. Gawkers from around the world drop into the shop, eager to see the master of the black-and-gray prison-style tat. If you want him to work on you, you’d better book months ahead of time. But Negrete’s life is more than just the art — it’s where the art comes from. And this book, Smile Now, Cry Later: Guns, Gangs, and Tattoos — My Life in Black and Gray (co-written with Steve Jones), tells the whole compelling tale.

The story starts earlier, with his mother’s Jewish family, who emigrated from Germany before Hitler rose to power in the early 1930s. Landing in racially segregated Los Angeles, they settled in once-Jewish Boyle Heights, where Negrete’s mother was born and raised, and where she later met Negrete’s father, a Chicano pachuco from East LA. In 1957, a year after Negrete’s birth, his father was sent to San Quentin and then Folsom for a failed train robbery; the year after that his mother was off to California Institute for Women on a manslaughter charge. That’s when things really went off the rails.

Sent to foster care with an abusive, white, Mormon family, who were as troubled as his birth family, Negrete became a surfer kid for a season — although he didn’t actually surf. After running away several times, usually to Seal Beach, he wound up in juvenile hall and did a stint in the California Youth Authority (CYA). It was in this setting that he reconnected with his Mexican and Chicano roots through gangbanging: “[W]ith white friends there was none of that ‘love for your homeboys’ thing going on. One day a guy was your friend and the next day he wasn’t.” When Negrete joined the San Gabriel gang Sangra, on the other hand, “[T]here was love there, so strong that you would be willing to go to battle for your friends and risk your life, or they would risk their lives for you.”

The gang epitomized family for Negrete, as it did for others, like the former LA Poet Laureate Luis Rodriguez, who came from a rival “set” (gang), Las Lomas. Rodriguez’s moving foreword to this book communicates the depth of what it meant to be Chicano in Los Angeles during the 1960s and ’70s, when Freddy and Luis put in “work” and did their time.

And it was hard time. Negrete’s years in the now-outmoded (though not yet completely dead) CYA were especially formative. It was there that he began to develop his tattoo style, drawing on his father’s tattoo artistry, with enthusiastic encouragement from guards. (Some of these guards even made an effort to come to see him win the Tattoo Artist of the Year Award in 1980, though it’s generally not permitted for guards to interact with former wards.) He also developed tenacity and a set of social skills in CYA that carried him through Preston reform school in Ione, California’s oldest youth prison. Negrete notes that, in prison, there are some mature men who just want to do their time and get out, but “in YA everyone’s a fuck up.” The Youth Authority’s destructive dynamic is described in vivid detail. Negrete didn’t emerge unscathed; he was stabbed and locked horns with the notoriously violent and unpredictable YA gangs, birthed from the relentless penal logic of California’s criminal system, which locked up far too many kids. Miraculously, he managed to negotiate and survive that perilous terrain, populated by guards, wards, gangs, and his own demons.

After his release, he got a job at Good Time Charlie’s Tattooland, where so many of Los Angeles’s major tattoo artists — including Mark Mahoney, Mike Brown, Shanghai Kate, and Jack Rudy — first got their start. Today, it’s run from Anaheim by Rudy, but in the late 1970s it was owned by Ed Hardy, who was fascinated by Negrete’s black-and-gray prison style. But this brief period was followed by his turn to religion, and his life as an “active Christian”; he became convinced that tattooing was sinful and left the art for a decade. Not unlike others who find religion in or after prison, he went all the way. Turning his attention to the causes of street kids and justice reform, he eventually became a pastor, and was married. But his Christian life would eventually fall apart, leading him into a severe depression. He plunged back into the drug scene and spent a year in LA County jail for a 1988 robbery.

Once he was free again, Rudy gave Negrete another chance at Good Time Charlie’s in San Diego. This led to an opportunity to work as lead artist on the film Blood In, Blood Out (1993). To date, Negrete has worked on over 30 Hollywood films. But the rest of the road wasn’t free of bumps. He violated his probation and served another year in County in 1993. After early release, he settled in Santa Barbara, where “life was good” and where Negrete opened a new tattoo venue, Rat-a-tattoo. But drugs would continue to plague his life, and a second marriage would fail. He was forced to leave Santa Barbara. His son Lorenzo struggled in school, got involved in gang activity, and was killed in a shooting. This triggered another downward spiral for Negrete. Drugs put him back in prison — this time Folsom — and later in Los Angeles County jail.

Then, Negrete was diagnosed with a congestive heart condition, which forced him to confront his own death as never before. He prayed and began to turn his life around. The last two chapters of this book chronicle the man’s self-reinvention and even redemption, as well as a stronger relationship with his son Isaiah. He was accepted into the Jewish rehabilitation center Beit T’Shuvah and began working at Mark Mahoney’s Shamrock Social Club Tattoo parlor, where he’s been for over 10 years. The rehabilitation was intense, requiring full-on commitment, which is essential to kick the challenge of drug addiction, and the community of Beit T’Shuvah and its practices of Jewish spirituality proved incredibly helpful for Negrete. In a sense, they helped him recover his Jewish identity, from his mother. Furthermore, his own Christian beliefs were never challenged by the Jewish community — he never denied Christ. His particular kind of theology is indigenous to Los Angeles, born of his own multicultural roots and experience.

As I read this gripping memoir, I reflected on the fact that Negrete’s story is a communal one, both dashed and rebuilt with the help of others, and ultimately highlighting the power of Angelenos to believe in one another, to accept one another as we really are. On a personal note, the book helped me understand the deep roots of the first tattoos I got as a 13-year-old: clown faces, “smile now, cry later.” Negrete invented this style, dubbed black-and-gray realism — which is a fitting designation for much of his life. Did it have to go that way? If “tough-on-crime” drug laws hadn’t been in effect when Negrete was a teenager and young adult, might he have gotten the help he needed much earlier? It’s a good thing these laws have now been tossed aside with the passage of Propositions 47 and 57. In Freddy Negrete’s life, we see a truer image of Los Angeles’s past and present — a truer image of ourselves. Angelenos are finally learning to take care of their own.

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Jason S. Sexton teaches at California State University, Fullerton, is the Editor of Boom California (UC Press), and is a Visiting Fellow at the UC Berkeley Center for the Study of Religion and the Center for the Study of Law and Society.