Shel Silverstein Has Pretty Much Lived The Most Kid-Unfriendly Life Imaginable

Shel Silverstein had at least two children, including a daughter named Shoshanna who stayed with her mother until she passed from cancer. Since Silverstein had no intention of being a father, he sent Shoshanna to live with an aunt and uncle. At the age of 11, she passed without Silverstein really getting to know her. He was said to have always felt guilty for not spending more time with his daughter and dedicated A Light In The Attic to her memory.

In an obituary written by David Mamet, the playwright noted of his good friend's feelings about his wife and daughter's passing, "And he told me that the terrible thing was not that they were dead, but that they stayed dead." 

As a child, Shel Silverstein was always drawing. Growing up, he was able to translate his childhood love for art into a few paying gigs for magazines like Sports Illustrated and Look. Eventually, he landed the job that would launch his career - creating cartoons for Playboy. The magazine had started only a few years earlier and Hugh Hefner was excited by Silverstein's work. 

In addition to gaining a larger audience for his cartoons, the new gig at Playboy meant Silverstein was finally able to make a living as an artist. Eventually, he took on more of a writer role at the magazine, creating a series of travelogues, complete with photographs and illustrations. 

Considering Shel Silverstein has become one of the most beloved children's book authors of the world, it's funny to think the thing that led him to write stories and poems for kids was his hatred of the genre. He was offended not only by the condescending writing style many children's authors used, but also the artwork. 

After writing Uncle Shelby's ABZ Book: A Primer for Tender Young Minds, a children's style book that was definitely not for children, a few friends finally convinced Silverstein to give writing a real children's book a shot. Lo and behold, the books were a global hit. 

Like many American men, Silverstein was drafted into the US Army in the early 1950s. He was sent to serve in the Korean War, but was luckily able to hold onto his love of art, becoming a cartoonist and writer for a military newspaper called Stars and Stripes. He quickly became known as a sort of rebel and some of his humorous illustrations received complaints from offended soldiers and officers.

In fact, a few of his cartoons almost got him court-martialed. Luckily, the controversy was caused by military officials not completely understanding Silverstein's message in the questionable pieces, and he was let off the hook. Misunderstanding or not, it quickly became evident that Shel Silverstein was not afraid of taboos, even in cartoon form. 

Shel Silverstein expressed frustration with readers examining his work too closely. For example, take his most famous cartoon where two men are chained in a prison cell. Their tattered clothing and unshaven faces show they've been stuck there for some time. The caption of the cartoon, as one man speaks to the other, reads, "Now, here's my plan." Silverstein thought this image was funny, but many people saw a deeper meaning in it and the cartoon was even used in psychological testing to observe people's reactions to it.

Silverstein expressed that people were reading too much into the drawing:  

You ask about the story behind it because everyone was, you know, trying to figure out the psychological and philosophical connotations of this, which is a lot of sh*t, because I don't do stuff that has any deeper meaning than what the stuff shows. Yeah, it's been used in psychological testing; it's been used by Alcoholics Anonymous to describe courage. You do something, you make it simple, and everybody else starts loading it up with deeper meanings."