Silverstein began drawing at age seven by tracing the works of Al Capp. He told Publishers Weekly: "When I was a kid—12 to 14, I'd much rather have been a good baseball player or a hit with the girls, but I couldn't play ball. I couldn't dance. Luckily, the girls didn't want me. Not much I could do about that. So I started to draw and to write. I was also lucky that I didn't have anybody to copy, be impressed by. I had developed my own style; I was creating before I knew there was a Thurber, a Benchley, a Price and a Steinberg. I never saw their work 'til I was around 30. By the time I got to where I was attracting girls, I was already into work, and it was more important to me. Not that I wouldn't rather make love, but the work has become a habit. "