Schoolly D Is Living the American Dream

A gangster rapper looks at 50.

A FEW DAYS LATER, SCHOOLLY SAID he wanted me to meet one of his five sisters, so that I could get a sense of how he grew up. “I don’t know what she’ll tell you,” he said. “I think she still thinks of me as 12 years old.” From Center City, we got in my Honda and drove to King of Prussia. Schoolly can’t drive, due to a seven-year-old DWI. I apologized for the state of my car, which was strewn with my daughter’s clothing, and Schoolly grinned and said, “I understand how it is, yo.” Schoolly has a 10-year-old daughter with his longtime girlfriend. For years they all lived together in Gladwyne, alongside “katrillionaires,” but recently Schoolly and his girlfriend separated, and he’s moved back to the city. (Schoolly also has a 23-year-old son from a different relationship.)

He directed me to a shopping mall, and after we killed a few minutes inside a Barnes & Noble (“They have a porn section here, only they call it ‘erotica,’ ha ha ha”), Schoolly got a text and walked into the parking lot. A woman in a thick black coat approached us and started to laugh. She held out her arms, and she and Schoolly embraced. Then I interviewed Gloria Branch while Schoolly hung out in Bed Bath & Beyond.

She was on her lunch break from an office job nearby. I asked her what Schoolly was like when he was a kid, and she said, “Well, I call him Jesse. When I’m mad at him, he gets Jesse Jr. And when I’m really mad, he gets the whole name—Jesse Bonds Weaver Jr.”

They grew up in a large family of nine kids—five girls, four boys—at the corner of 52nd and Parkside, behind the Mann Center for the Performing Arts. Branch recognized Jesse’s artistic talent early on; he would videotape his favorite Saturday-morning cartoons,­ then pause the frames and draw the characters, over and over, until they were perfect. “He was the youngest boy,” Branch said, “spoiled by all the women.” Their father worked two jobs, one at the post office and the other at the General Motors plant in Camden. He told his kids to make sure they never worked in a factory like him.

I asked Branch if she had listened to Schoolly’s records. “After the first couple, not really,” she said. “I’m a smooth-jazz type of girl.” However, she does own one of Schoolly’s earliest records, which is now a collector’s item, “and I got him to sign it. And that is mine. No one is ever getting that, no no no.” “What did she say about me?” Schoolly asked once we were back in my car. “Anything really funny?”

We drove into West Philly. Schoolly had another person he wanted me to meet. He directed me to a street off Girard Avenue. We got out, and I left my bag in the car. Schoolly said, “You might want to bring your bag with you. Just sayin’.” He knocked on the door of a tan-and-burgundy rowhouse. A woman answered. We peeked around the door and saw an obese man with a breathing tube sitting in a recliner, watching a History Channel show about John Dillinger. Schoolly leaned down to hug the man, and I went to shake his hand. He gave me a fist bump instead. “Pimp,” he said, nodding.

Pimp Pretty, whose real name is Nicholas Garstar, grew up with Schoolly at 52nd and Parkside. For the next 45 minutes, he and Schoolly took turns telling stories about the old neighborhood.

“It’s a rough world,” Schoolly said. “You had to be prepared for the rest of your life to fight at a moment’s notice.”

“I was the little fat kid who could,” Pimp said. Unlike Schoolly, he lacked brothers to protect him from the local hoods. Once, one of Schoolly’s older brothers heard that a kid was talking shit about Schoolly. The brother didn’t say a word. He simply hammered a nail into a two-by-four, approached the kid, and swung. Schoolly, telling this story, grabbed his temples and rocked forward in his chair. “Have you ever heard the sound of a nail sucking itself out of a kid’s skull?” (The brother is now in prison for a different crime, robbery with threat of immediate injury.)

So that was where they came from. Pimp and Schoolly looked out for each other, and it bonded them forever. In 1982, when Schoolly began pressing his own records on his own label and hawking them to record stores out of the back of his father’s truck, and when he started getting calls from established hip-hop acts like 2 Live Crew, asking him to go on tour, there was no question. Pimp would come with him. Pimp was there, backstage, when “crazy little girls” would seek out Schoolly after a show. Pimp was there at the New York parties, in a coat of white cashmere and dark sunglasses. (“I still got my white cashmere.”) Pimp was there in the Miami airport when he and Schoolly discovered their then-manager smuggling a coat full of bootlegged Schoolly records, at which point Pimp and Schoolly beat the man with a champagne bottle and canceled his plane ticket back to Philly. The way they told me this story, there was something almost sweet about it—the tale of a family banding­ together to fend off a threat. Compared to a nail in the skull, a beat-down with a champagne bottle was almost kind.

In the mid-’80s, Schoolly signed with Jive Records, a major corporate label, and began to broaden his lyrical repertoire beyond the topics that once led the New Republic to call him “a rapper from whom you would flee in abject terror if you saw him walking toward you late at night.” (“I was pretty fuckin’ scary,” Schoolly said. “I think I even scared myself sometimes.”) On a track from 1988’s Smoke Some Kill (“kill” is slang for “weed”), he intercut his lyrics with a speech by H. Rap Brown, the black activist. On 1989’s Am I Black Enough For You?, Schoolly quoted Malcolm X and advised listeners to leave the fuckin’ crack alone. Schoolly earned, and burned through, about $10 million between 1985 and the early 2000s—chump change compared to the bounties that his successors would reap, but still, enough for him to afford a lavish NoLibs loft with 35-foot ceilings and a remote-control gate that allowed him to drive his Jaguar straight into the house. He called it his Bat Cave.

He was impulsive. Once, while opening for James Brown in front of 100,000 people in London, Schoolly walked off the stage in the middle of his set. “I got bored,” he explained. “The crowd thought it was part of the show. They got worked up. They got really worked up. I did five more songs. They were fuckin’ pleased. So I go back to get my pay, and James Brown comes through. He’s like, ‘Schoolly! Gidyomodafckczbtitmey!’ I’m like, what the fuck did he say? ‘Get your money, get the fuck out, ’cause I’m about to get MY money!’” The promoters went to fetch four silver suitcases full of cash for James Brown, and in the ensuing rush they handed Schoolly two envelopes, not one. They paid him twice. “So I make like 35 grand for the afternoon. Ha!” There’s something fundamental about this story—Schoolly opens for his childhood hero and walks off the stage because he’s bored, yet it somehow only makes him richer and more beloved.

In 1996, Schoolly’s father passed away after a long illness. Jesse Weaver Sr. had never listened to any of his son’s records until a week before he died. Around this time, Schoolly was extending himself into a new musical realm, working on a film score for the Bronx-born director Abel Ferrara. Schoolly drank heavily to deal with the stress and grief. Drug dealers and hookers found their way to the Bat Cave. “I was stretching myself a few ways, like we all do,” Schoolly says. “We start thinking that outside help, outside help. Some people use powder, some people use weed, some people use alcohol. … It works out the first year, but then in year two, three, four, five and six, you start sayin’ Whoa.” After a couple of stints in detox facilities, Schoolly stopped drinking. “I found my way back to my cartoon world,” he says. But more than that, he found a completely new audience.