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

Many children grew up reading Shel Silverstein's poetry, but stories about the poet's darker side depict him in a completely different light. Hints to his creative yet twisted mind appear in some of Silverstein's creepy poems, but the real Shel Silverstein personality emerged through his work for adults, including songs, plays, and cartoons. Silverstein was a private man who never gave many interviews. Instead, he threw himself into almost every area of creative expression.

Born in 1930, Silverstein began drawing at a young age but was quickly seen as a rebel with controversial ideas and the lifestyle of a drifter. Some of Silverstein's best books, like The Giving Tree, Where the Sidewalk Ends, and A Light in the Attic, harbor interesting insights into the genius' mind. Although these are the titles that brought him the most fame, they also created some controversy by appearing on banned book lists. So, what was Shel Silverstein like? What really lurked in the mind of a man who possessed tremendous amounts of imagination, creative passion, and a twisted sense of humor? These dark Shel Silverstein stories may help shine a little light in that attic. 

  • He Sent Away His Young Daughter When Her Mother Passed Away, Only To Have The Child Die At An Early Age, Too

    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." 

  • Playboy Jumpstarted Silverstein's Career As A Cartoonist

    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. 

  • Shel Silverstein Hated The Children's Book Genre

    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. 

  • A Cartoon He Drew For The Army Almost Got Him Court-Martialed

    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. 

  • His Most Famous Cartoon Was Used For Psychological Testing, Which He Thought Was Ridiculous

    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."

  • Shel Silverstein Penned Some Pretty Raunchy Songs

    In addition to being a cartoonist, children's author, and playwright, Shel Silverstein was also a musician. During his career, he created nine albums, as well as one unreleased album with more adult content. He also wrote songs for other artists, including Dr. Hook and Johnny Cash, since his fans were unimpressed with his own voice. He once claimed, "I don't see anyone running out and buying my records, but I like the way I sing."

    In addition to songs about substances, Silverstein also penned songs about venereal disease, self-pleasure, nude beaches, and sexuality. Clearly, he didn't want his career to focus on one art form or one audience, stating, "I run into difficulty because people want to find a nice clean handle for everyone, and you can't do that for any creative person. Nobody has only one side. You want people to allow for all of you."