When former “procurer of women” Iceberg Slim (Robert Beck) published his now iconic first book Pimp with Holloway House in 1967, he had already fled “the game” in the Chicago streets and was living as a square in California. Kindasorta married to a White woman named Betty, with whom he would have three daughters, Slim was working as an exterminator in Los Angeles while trying to figure out his next move on the big chessboard of life. 

At the urging of his mother, he exposed his past explicit exploits to the woman that he loved. Instead of being repulsed, Betty encouraged her sweet daddy to write a book about his streetwise adventures. With Beck dictating, Betty typed the pages, and Pimp was constructed. 

A few months later, the book was through. As though struck with luck, a few days later Betty saw an ad placed by Holloway House in the Los Angeles Sentinel: “Black writers needed! Publishers will pay you for your stories!”

Promoted as a fictional autobiography, in the 46 years since its release Pimp: The Story of My Life has sold millions of copies, been translated into different languages and has influenced a generation of creative folks including Brooklyn born mogul Jay Z, Scottish scribe Irvine Welsh and, of course, rapper Ice-T. In fact, the pretty boy rapper introduced his manager Jorge Hinojosa to Slim’s novels 28 years ago.

“I was 19 years old, a former prep school kid, when Ice-T gave me a collection of Iceberg Slim’s books,” Hinojosa remembers. “Believe me, that was a profound experience.” Almost 30 years later, the close encounter with Slim’s wildstyle fictional autobiographies, as well as the complexity of the writer’s post-hustling life, inspired Hinojosa to direct the already critically acclaimed documentary, Iceberg Slim: Portrait of a Pimp.

After four years in the making, Portrait of a Pimp delves deep into the long life of the writer whose brutal books—which include Trick Baby (1967) and Mama Black Widow (1969)—depicted “the ghetto experience” in all its gore, guts and glory. 

“Iceberg Slim’s world was a violent one, but he wrote about it so poetically,” Hinojosa says. “He wrote about these grime situations very artfully. To me, he is like a perfect combination of Mark Twain and Hannibal Lecter. Twain, because he was able to write about his strange world so perfectly; Lecter, because of how he was able to manipulate so well using just his intellect and prowess.”

The film contains stunning archival footage, period photographs, cool Ralph Bakshi-inspired animation and interviews with such luminaries as Quincy Jones, Snoop Lion, Bishop Magic Don Juan and actor/director Bill Duke, who once attempted to get Pimp made into a feature film. 

Hip-hop renaissance man Fab Five Freddy, whom Ice-T says introduced him to Slim via a telephone conversation back in the day, befriended the former player in the late 1980s. “I had read his books when I was a teenager growing up in Bed-Stuy, Brooklyn,” remembers the artist and former Yo! MTV Raps host. “Iceberg Slim’s books were a precursor to Blaxploitation films like The Mack and Willie Dynamite, as well as inspiring a million rap records.”

Originally connecting through Iceberg’s publisher Holloway House, they spent many hours talking inside his crib on Crenshaw, where the New York native got to know very well the man instead of the myth. “He told me that his mother encouraged him to be a lawyer, but he instead choice the streets. Later, his books took us on a journey into that lifestyle the way nobody did. At the time, there wasn’t anyone else doing it.”  

While his publishers at Holloway were also the owners of the Black nudie magazine Players, they later published the pulp paperbacks of druggie writer and Slim disciple Donald Goines, as well as Odie Hawkins, Joe Nazel and Cole Riley. “Iceberg’s novels were essentially urban cautionary tales, where the dreams of the ghetto could turn on you and bite you in the ass,” Riley says. “That’s why they have a definite lasting value.”

Riley, who published Hot Snake Nights and Rough Trade with the small press in the 1970s, says, “The pay was almost nothing, but I learned a lot. I got a note of approval from the master himself, Iceberg, telling me that he liked my style and ‘don’t let the ofays change me.’ ”

Although Pimp is Iceberg’s most famous book, cultural critic and Iceberg Slim aficionado Mark McCord believes that Mama Black Widow was the writer’s masterpiece. “No other book articulates the loneliness and desperate struggle the way Mama does. The works of James Baldwin and Ralph Ellison are cool, but they never spoke to me the way Iceberg Slim did. He was the master of metaphors. Iceberg could make the words jump off the page and breakdance. He was the truth.”

Literary agent Marc Gerald, who also cites Mama Black Widow as his favorite Iceberg book, couldn’t agree more. “Slim’s books have a dark heart, but his characters are timeless,” Gerald says. “His take on the ways of the street was beyond cool, and often a little sad.”

Unfortunately, because of bad contracts and alleged shady dealings, Iceberg Slim died penniless on April 30, 1992. His friend Mike Tyson, who went to Iceberg for marriage advice, gave him money in advance to pay for the funeral.   

In 2011, when the rights for Iceberg’s mack daddy tomes reverted to his three daughters, Gerald was influential in getting them a new publishing deal with Cash Money Content. “[Cash Money’s Bryan ‘Birdman’ Williams and Ronald ‘Slim’ Williams] were, of course, familiar with Iceberg’s books, and they were thrilled to be involved,” Gerald says.

Back in 1999, after the success of Soul Souljah’s wildfire-success novel The Coldest Winter Ever, a new generation of authors began writing about their ’hoods from a hip-hop perspective.

“Iceberg Slim is the grandfather of street hip-hop lit,” says Washington, D.C. based novelist Kenji Jasper. “He told stories about the urban underbelly before such a term even existed. To look back at it now, he gave three-dimensional shape to the worlds of pimps, pushers and prostitutes that required a circumspect kind of vision that most brothers of that era probably didn’t have.”

Says director Hinojosa, “My goal with this project was to not just show a snapshot of Iceberg, but the full spectrum of his life.” Going from pimping women to pimping the page, Iceberg Slim: Portrait of a Pimp is a must-see for both players and lames.

Iceberg Slim: Portrait of a Pimp opens Friday, July 19, 2013 in New York and other select cities. The film is also available on iTunes.

Cultural critic Michael A. Gonzales has written cover stories for VibeUptownEssenceXXL, Wax Poetics and elsewhere. He's also written for New York and The Village Voice. Read him at Blackadelic Pop and follow him on Twitter @gonzomike.