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===="Now here's my plan..."==== [[File:Nowplansilverstein.jpg|thumb|160px|"Now here's my plan...", Silverstein's best known cartoon of the 1950s, became the title of his 1960 cartoon collection]] A cartoon he made during the 1950s was featured on the cover of his next cartoon collection, titled ''Now Here's My Plan: A Book of Futilities'', which was published by [[Simon & Schuster]] in 1960. Silverstein biographer Lisa Rogak wrote: <blockquote>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."<ref name=rogak/></blockquote> Silverstein's cartoons appeared in issues of ''Playboy'' from 1957 through the mid-1970s, and one of his ''Playboy'' features was expanded into ''[[Uncle Shelby's ABZ Book]]'' (Simon & Schuster, 1961), his first book of new, original material for adults.
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