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Shel Silverstein taught himself to draw at the age of 5 by tracing the comics in the newspapers. When he started writing his own stories he also began drawing stories to go along with them. As he got older his drawings became more relatable to adults. In the 1950s, he drew for the Military magazine Stars and Stripes while serving in Japan and Korea. When he returned home, to Chicago, his illustrations were published in magazines such as Look, Sports Illustrated and This Week. The cartoon that made him famous was on the cover of his collection Now Here's My Plan: A Book of Futilities in 1960. Then he got a permanent job at Playboy and drew with them until the mid 1970s.
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