Now Here's My Plan: A Book of Futilities

A cartoon he made during the 1950s was featured on the cover of his next cartoon collection, titled Now Here's My A Book of Futilities, which was published by Simon & Schuster in 1960. Silverstein biographer Lisa Rogak The cartoon on the cover that provides the book's title would turn out to be one of his most famous and often-cited cartoons. In the cartoon, two prisoners are chained to the wall of a prison cell. Both their hands and feet are shackled. One says to the other, "Now here's my plan." Silverstein was both fascinated and distressed by the amount of analysis and commentary that almost immediately began to swirl around the cartoon. "A lot of people said it was a very pessimistic cartoon, which I don't think it is at all," he said. "There's a lot of hope even in a hopeless situation. They analyze it and question it. I did this cartoon because I had an idea about a funny situation about two guys."