Before Ice-T, born Tracy Marrow, became a Grammy-winning rap artist, police-procedural detective, and reality-show star, he was a Los Angeles– area high-school student suffering through required readings like Moby Dick and The Adventures of Tom Sawyer. It wasn’t until he got his hands on a paperback copy of Iceberg Slim’s 1969 memoir, Pimp: The Story of My Life—which, he says, cool upperclassmen toted in the back pocket of their Levis each day—that he felt he connected to something.

“I started to read it, and I could quote lines out of it,” Ice-T told VF.com during a recent interview. “It just did wonders for my life. I started to idolize the books. Later on in my life, when I got into music, I started to write [songs], but I would write them like books, like stories.” His admiration for Iceberg inspired his rap name, his creative career, and his gift choices—the rapper and Law and Order: Special Victims Unitstar has presented a copy of the book, which has drawn comparisons to the groundbreaking literature of Ralph Ellison, to everyone from his daughter to his longtime manager, Jorge Hinojosa, as a “crash course” on his life.

More than three decades after first discovering the book, when mulling over possible film projects, Ice-T decided with Hinojosa to investigate Iceberg Slim’s complex life in a documentary. With the help of other Iceberg Slim devotees, such as Snoop Dogg, Bill Duke, and Chris Rock (who hands out copies of Pimp: The Story of My Lifeas wrap presents)—along with archival footage and interviews with members of Slim’s family—first- time director Hinojosa and executive producer Ice-T have pieced together a fascinating, complex account of the criminal turned best-selling author’s life in Iceberg Slim: Portrait of a Pimp. Introduced to prostitution by his mother, Slim (born Robert Beck) ultimately turned against it after jail time and drug dependency and, with the help of his wife, recorded his experiences in the revolutionary memoir, which both artfully depicts the seedy underworld he inhabited and cautions readers against it.

To discuss their documentary, Ice-T and Hinojosa sat down with us recently at the Toronto International Film Festival. Among the other topics covered: the enduring sexiness of the criminal lifestyle, Ice-T’s favorite line from Fargo, and why the Gangsta Rap artist might start making children’s movies next.

Julie Miller: This was such an interesting, multi-layered film.

Jorge Hinojosa: Thank you. I went through mental anguish making this thing, beginning with, “What am I doing spending all of this money?” There were points where I couldn’t even watch the rough cut. But you just go back to it, keep hammering, and then you get it done. It’s a relief, but you’re also happy that you suffered through this. Then I look at [Ice-T], and he makes everything look easy.

Ice-T: Well, it’s part of art. Art is something you have to be willing to bare yourself for. A lot of people can’t take the hit and the rejection. But Jorge is my manager. He’s stepping in the art. He’s writing a book. This is a new thing. A lot of people won’t be able to be artists because they can’t take the rejection. It’s such a high-risk game. You put it all out there, but the rewards are incredible.

Ice-T, in the documentary you talk about how you originally misinterpreted the book and pursued crime rather than art.

Ice-T: Right, I misinterpreted the book and so I got in the street. I was doing all kinds of heavy stuff. I had a lot of false starts before I got it right. When I actually finally got involved in that game, I realized it was more a headache than anything else. Like I said in the documentary, we were trying to pimp some chicks and they stole our car! So, I went off and started making my own money.