Schoolly D Is Living the American Dream

A gangster rapper looks at 50.

I’M BORED LET’S BOUNCE, SCHOOLLY TEXTED. It was 10 o’clock in Old City, and he was trapped in a place called Cipher Prime. When he first heard about the party, he thought that Cipher Prime was a steakhouse, but instead it turned out to be a tech company that designs video games.

If not for two things, Schoolly would have left already. One was the presence of his friend Susanna, an extremely thin young woman with a tattoo of an origami crane on the inside of her left wrist. The other was the spread of fresh-baked Christmas cookies. Schoolly’s standard contract rider says that he must be provided with cake or cookies. The cookies must be sugar, oatmeal raisin or chocolate chip—soft and fresh-baked at each performance. “I’ve been to enough of these joints where it’s like, you eat as many cookies as you can, then bolt,” he said. (Schoolly is sometimes paid to appear at parties, but that night he was there because Susanna invited him.)

Schoolly had set himself up in a cavelike computer room. He had found a bottle of vodka and placed it next to a mouse pad, for ambience. Susanna came by every so often and sat on his lap.

After a time, he got up to leave, then noticed a busty woman in a black tank top installing a stripper pole. wait stripper pole, he texted. The woman tried to suspend herself horizontally from the pole. She dropped to the ground and laughed nervously.

Schoolly grabbed the pole, jumped, then thought better of it and let go.

“Schoolly!” he said, scolding himself. “You fuckin’ asshole! You’re 50!”

A cute woman in a black turtleneck, black leggings and a black skirt now approached Schoolly and asked to take a picture with him. Schoolly laughed and put his arm around her. It turned out the woman was dating a writer for Pitchfork Media, the influential music-review website produced mostly by young white men. She turned to me. Her boyfriend, she said, “told me all about Schoolly. He’s wonderful.”

It’s easy to see why people, especially people in my generation, in their 20s and early 30s, respond to Schoolly D. When we were kids, we watched gangster-rap videos on MTV. Gangster rap was something raw and new that scared our parents. Today, it’s such a familiar part of the culture that those early songs and videos evoke feelings of nostalgia. As an art form, it has traveled the well-worn path from revolution to satire target. Now we get our gangster rap filtered through the avatar of a talking milkshake on Cartoon Network.

And who is the man who hovers, ageless, at both extremes, like some pop-culture guardian angel? Schoolly D, that’s who. And he’s not bitter about the way his career turned out, even though if there’s anyone with cause to be bitter, it’s Schoolly D, who spawned a multibillion-dollar industry and then watched other men collect the eye-popping checks. He was vital and terrifying when he was young, and he’s funny and happy when he’s older, the kind of happy that makes you question the way you’re living your own life. You can experience the reflected glow of that happiness for yourself if you’re lucky enough to live in Philadelphia, a city where on a Thursday you can show up at a video-game-company party and eat sugar cookies from the same plate as the architect of a major cultural movement, or where, three days later, on a Sunday night, you can duck down an alley off Broad Street and pay $5 to an enormous man with elaborately braided hair and listen to the architect spin records for sleepy-eyed men and topless women.

“I got my girl Devon comin’ up,” Schoolly crooned, ensconced in a deejay booth at the Gold Club. “Aw, gimme a smile, baby, it’s Schoolly D night.”

While the strippers waited to dance on a patch of lacquered hardwood no bigger than a janitor’s closet, they leaned over the deejay booth and talked to Schoolly. For a few seconds, their eyes lost that glazed look, that 50-yard stare. They laughed.

He played old-school soul. James Brown. Otis Redding. I chatted with the bartender, a platinum blonde with flaring black eyebrows. “Sundays are always fun with Schoolly,” she said. “Other deejays just say ‘And heeeeere’s Candy,’ but he plays music.”

Schoolly descended from the booth. “This is so not what it looks like,” he told me. “I’m not a strip-club person. I’d rather be at home.” He said I didn’t have to stick around for the whole night if I didn’t want to. The women, he said, were getting antsy. I was scaring them with my questions.

I told him I’d take off. He brightened. “My brotha.”