After almost two decades on the road as a drummer for various rock and jazz bands, Chris Pyle, 44, went back to the drawing board — literally. He’d taught himself to draw as a child, studying ”classic” caricaturists Miguel Covarrubias and Paolo Garretto, whose work appeared in the Depression-era Vanity Fair. Then, at the end of the ’80s, he decided to try his hand at art and began making large-scale paintings for galleries. Still, ”something was missing,” Pyle says. ”That’s when I decided to get involved in illustration.” An EW contributor since the mid-1990s, Pyle, who lives in Indianapolis with his wife, Lou Ann, and his son, Leo, 14, sprinkled the Best of 1999 with his twilit, pseudo-cubist celebs. He counts Drew Carey among the easiest stars to capture (even if he did have to complete the piece under the pressure of a deadline), but found his highest highs and lowest lows in a recent treatment of the Friends cast. ”Those people change everything about themselves every two weeks,” he says. ”Their clothes, their hair…Matthew Perry was pretty tough. He goes up and down. You don’t know whether to do him with a full face or a thin face.” Do both, Chris, we might need them.