Cartoons
Born in Chicago, Silverstein began drawing at age 12 by tracing the works of Al Capp. He told Jean Mercier of Publishers Weekly: "When I was a kid—12 to 14, around there—I would 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 till 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."
He graduated from Theodore Roosevelt High School. He began studying art at the University of Illinois but was forced to leave due to bad grades. Then he attended the Art Institute of Chicago but left after one year. He was first published in the Roosevelt Torch (a student newspaper at Roosevelt University), where he studied English after leaving the Art Institute. In 1953 he was drafted by the US Army and served in Japan and Korea. In the military, his cartoons were published in Pacific Stars and Stripes, where he had originally been assigned to do layouts and paste-up. His first book, Take Ten, a compilation of his military Take Ten cartoon series was published by Pacific Stars and Stripes in 1955. He later said his time in college was a waste and would have been better spent traveling around the world meeting people.
Returning to Chicago, Silverstein began submitting cartoons to magazines while also selling hot dogs at Chicago ballparks. His cartoons began appearing in Look, Sports Illustrated and This Week.
Mass-market paperback readers across America were introduced to Silverstein in 1956 when Take Ten was reprinted by Ballantine Books as Grab Your Socks! with a foreword by Bill Mauldin.
In 1957, he became one of the leading cartoonists in Playboy, which sent him around the world to create an illustrated travel journal with reports from far-flung locales. During the 1950s and 1960s, he produced 23 installments called "Shel Silverstein Visits..." as a feature for Playboy. Employing a sketchbook format with typewriter-styled captions, he documented his own experiences at such locations as a New Jersey nudist colony, the Chicago White Sox training camp, San Francisco's Haight-Ashbury district, Fire Island, Mexico, London, Paris, Spain and Africa. In a Swiss village, he drew himself complaining, "I'll give them 15 more minutes, and if nobody yodels, I'm going back to the hotel." These illustrated travel essays were collected by the publisher Fireside in Playboy's Silverstein Around the World, published in 2007 with a foreword by Hugh Hefner and an introduction by music journalist Mitch Myers.
In a similar vein were his illustrations for John Sack's Report from Practically Nowhere (1959), a collection of humorous travel vignettes previously appearing in Playboy and other magazines.
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