What Do You Call A Black Man Who Flies An Airplane?” - Asks R. Kelly

R. Kelly whirls around, straining to look out his car’s rear window. “You see that?” asks the R&B star, sitting in the middle row of a black SUV cruising down Manhattan’s West Side.

On this sparkling afternoon in early fall, he’s just noticed a young woman driving a red sedan one lane over. “Damn,” says Kelly, as the smoke from his cigar curls along his giant gold watch and up past his diamond earring. “Uhm-hmm,” says a bearded assistant in a baseball cap from the backseat.

This man’s job, as best I can tell, is to light his boss’s cigar and carry around a small duffel bag. The SUV pulls even with the woman’s car, and Kelly, on his way to a Chelsea recording studio, goes quiet, staring at the woman as she looks straight ahead.