Intern Steve Conquers the Rap World

In the golden age of underground hip-hop, a small-town kid gets behind the wheel on a tour that is doomed from the start.

Illustrations by Nate Beaty

It was at least one in the morning and somewhere in Philadelphia I was driving a van full of rappers to an appearance on Philly native and pioneering female emcee Bahamadia’s weekly radio show, B-Sides. This was in late February, 1999. It was cold and damp and I had no cell phone, no GPS. I followed another van filled with still more rappers and driven by an employee of Zero Hour Records, the parent company of 3-2-1 Records, the fledgling New York City hip-hop label for which I was a mere intern.

We were neck deep in a long-weekend tour to promote Skeme Team’s new single, “Plan A.” I was twenty-two, a recent college grad with a B.A. in jazz performance, and I was driving around a bunch of guys who wouldn’t know a whole note from a hole in the ground. Worse, I was doing it for free, out of a love of hip-hop and a naïve assumption that going on tour would be a cool thing. Cool things were the reason I’d moved to New York in the first place.

We were late. We were…