Philly Hip-Hop Legend Schoolly D Has a Message for Wannabe Rappers

Plus, he weighs in on cheesesteak battles and the desserts at Fork.

Schoolly D

Schoolly D / Photograph by Stevie Chris

Meek Mill. Lil Uzi Vert. Tierra Whack. Black Thought. All famous rappers from Philadelphia. But long before they started making rhymes and beats — and, indeed, long before some of them were even born — Schoolly D was the undisputed heavyweight champion of Philly rap. We caught up with Schoolly D ahead of his Philly Music Festival show this month.

The name on my birth certificate is … Jesse Bonds Weaver Jr. When I needed a rap name, I didn’t want to be Jesse B. I loved to school people, so Schoolly D was born. The “D” stands for “dunk” — I could slam-dunk a basketball.

People who say I invented gangsta rap are … absolutely correct. I released the first known gangsta rap album, Schoolly D. Some Spin journalist called the genre “gangsta rap” because he was interviewing these gang members in Baltimore and all they were listening to were my songs, like “P.S.K. What Does It Mean?,” so the journalist said, “This must be gangsta rap.” And that is how that all started.

I was born in … West Philly, at 52nd and Parkside. Grew up there and in Georgia. In the Black community, when you did something wrong, they would send you to your family in the South.

My first car was … an old, dirty Mustang. Burgundy. It was so rusty that my sister made me resell it after two weeks.

These days, I live in … a condo in Germantown.

I knew I wanted to be a rapper when … I saw Richard Pryor on Johnny Carson in 1976. And I listened to the way he talked and his rhythm. I turned to my mother and said, “That’s what I want to do, but with music.”

When I’m not rapping … I’m painting and sculpting. I just came back from a gallery showing in L.A., and I sell stuff at Sotheby’s and all over the world.

My secret junk food obsession is … watermelon in a bowl with salt on it, topped with vanilla ice cream.

The biggest difference between rap today and when I started out is … that you couldn’t get a deal unless you were actually good back then. And you could also tell where a rapper was from by the way they sounded, but now, it all sounds the same, so there’s no regionality to it.

schoolly d in 1986

Schoolly D in London in 1986 (Getty Images)

My relationship status is … as complicated as always.

For my next project … I am doing a wax boxed set of all my music and repainting­ all my album covers. And Sony Pictures is doing a story of my life.

The best restaurant in Philadelphia is … Fork. Hands down. The desserts there are just outrageous.

I like to collect … mid-century­ lamps. I have lamps that were on Star Trek and other TV shows, but my favorite one is from Dr. No.

Some of the biggest acts I’ve opened for are … James Brown and Prince. James Brown was in London. I don’t remember the year. James knew who I was and at one point backstage, he says to me, “Schoolly: Get your money and then get the fuck out, ’cause I’m about to get my money.” The promoter goes and gets these silver cases filled with money for James. And in the middle of all the chaos, the promoter accidentally paid me twice.

The last time I had a cheesesteak was at … Chubby’s in Roxborough. So much better than Dalessandro’s across the street. We did a blind taste test. They don’t even compare.

When I released my first album in 1985 … Philly was in turmoil­ over the MOVE situation. I was in West Philly when they dropped the bomb, and I thought, “This is some Vietnam shit.”

Some of my famous friends include Christopher Walken and Laurence Fishburne, from when I worked on King of New York with them.

If I want to relax … I watch film noir.

When people today tell me they want to become a rapper, I tell them … to eat a dick. They need to become a doctor or a lawyer. Most wannabe rappers suck, and you’re not even allowed to tell people they suck anymore. The world is a strange, strange place.

Published as “One of Us: Schooly D” in the October 2023 issue of Philadelphia magazine.