Schoolly D Is Living the American Dream

A gangster rapper looks at 50.


I walked into a bar with the rapper Schoolly D not long ago. It was a new place on 21st Street, so new that it still had the name of the old establishment­ on the door. Schoolly had recently begun deejaying here as part of a series of famous Philly DJs, but tonight he wasn’t working. He was trying “to get into some trouble,” he told me. He flashed a toothy grin.

Do you know Schoolly? No? Well, have you heard of Jay-Z? Kanye West? Ice-T or Ice Cube? Any rapper at all, really? You probably wouldn’t have, if not for Schoolly D. Exactly 30 years ago, Schoolly, whose real name is Jesse Bonds Weaver Jr., wrote the world’s first gangster-rap anthem, a tune he called “Gangster Boogie.” He did it right here in Philly. Many people are under the impression that gangster rap is originally a Los Angeles phenomenon, or a New York one. But it was Schoolly, the Philadelphian, who became the first rapper to make bitches and hos, drugs and guns, his exclusive lyrical territory. He was the first to channel the lives of hustlers, gangsters and pimps—people who sold dope and sold sex and broke the law because there were no other options for economic advancement­ in their neighborhoods­—into a new kind of street poetry. He was the first to fashion a motif of the word “nigga.” (Once, he rapped about walking into a bar and seeing a sucker-­ass nigga tryin’ to sound like me. Put my pistol up against his head. I said, Sucker-ass nigga, I should shoot you dead.) He was also one of the first to slow down the cadence of rap from a fast babble, a faucet of words, to a drip, so that you could hear every word with beautiful, terrible clarity. Like Langston Hughes before him, Schoolly was a black man writing a letter to America about a particular slice of the black experience.

Anyways, as soon as Schoolly and I walked into this particular bar, Schoolly spotted a young blond woman near the door. She was tall, with wavy hair. He walked toward her. Schoolly is sprightly and muscular and has a smooth, unlined face. Wikipedia says he’s 45. He looks 30. He’s actually 49. On this night, he wore a light gray Kangol cap with skinny black jeans and black leather Steve Madden boots. He put his hands on the blonde’s hips and twirled her around 360 degrees. Then he spun off of her like a tailback and lurched into the darkened main room of the bar, where he bear-hugged another, different blonde, who happened to be a former top 100 finisher on American Idol. Her name is Erika Schiff. Schiff is lithe and plump-lipped and trying to launch a music career. I followed in Schoolly’s wake with a pen and notepad, awkwardly interviewing the women he had engaged, asking the first blonde how she knew Schoolly (“Schoolly?” she said, confused. “No, I don’t know him at all”) and getting a quote from the second blonde, from Schiff, the Idol girl. “Schoolly’s not just the gangster,” Schiff said. “He has these other sides. He’s sweet.” Then I sat down at a table in the corner next to a heavyset guy with bulging eyes, and I watched Schoolly and the Idol girl start to dance. I took a sip of beer and looked up, and he was kissing her. Not amorously. Not exactly. Just a peck on the lips. Then another peck. She was laughing and throwing her hair back.

After a time, the heavyset guy next to me, who was drinking a vodka on the rocks, and who had been silent up until now, started to talk. It was late, a little after 1 a.m., and this was the third bar/party that Schoolly and I had visited that night, and I was pretty buzzed. The heavyset guy said something like—I’m paraphrasing—“A lot of the stuff on those early records, the hustling, the lifestyle, Schoolly got that from me, okay? It was my experience he was talking about.” He pointed to his heart with both hands.

The heavyset guy told me that he was a figure of importance from Schoolly’s past. He told me about how he had been struggling lately, in the recession. How he had a kid. How he had tried to support his family by starting an appliance service but the company had fallen through. How things were looking up because he had a package coming through in the near future. As soon as the package came through, he said, everything was going to be all right. He nodded his head vigorously and glanced at Schoolly D, who was still dancing with the Idol girl.

Later that same night, I mentioned this conversation to Schoolly. He was lucid. All along, Schoolly had been drinking water and passing it off as vodka. He has found, over the years, that people like to see musicians drinking, and although he doesn’t binge—not anymore—he doesn’t wish to disappoint. This was what the original gangster rapper had meant by getting into trouble: drinking water and dancing. (Although a few days hence, in the shotgun seat of my car, he will suddenly shoot me a nervous glance and ask if any of my sources are telling me that Schoolly D is a coke fiend. He’ll look relieved when I tell him no.)

That night, Schoolly D thought for a moment about the heavyset guy, then said, “He’s one of those cats who believed it when people told him that there were some places he couldn’t go.”