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

Updated April 16, 2020 152.9k views13 items

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. 

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  • 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."

  • Silverstein Loved Women Almost As Much As His Work

    Silverstein spent a few years living at the Playboy Mansion and was a devoted fan of women throughout his life. However, he didn't have much luck when he was younger. When talking about his college experience, he remembered, "I didn't get laid much. I didn't learn much. Those are the two worst things that can happen to a guy."

    As he became more successful and women became more interested in him, he always made sure they were aware he did not want a relationship. The 1966 Playmate of the Year, Diane Chandler, noted, "He instantly saw the signs and would say something like, 'Well, let's see, where shall I put you on my list?' to let the girls know that they shouldn't expect anything from him." 

    Silverstein once said in an interview, "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 Wrote A Disturbing Sequel To 'A Boy Named Sue'

    Johnny Cash once threw a party and invited some of his musician friends to share the latest pieces they'd been working on. Among offerings from Joni Mitchell, Bob Dylan, and Kris Kristofferson, Shel Silverstein sang, "A Boy Named Sue." At the urging of his wife, Cash sang the song at a performance at San Quentin prison and knew it would be a hit. Silverstein later decided to write a sequel to the song where the father was the main character.

    But "The Father of a Boy Named Sue" reveals a side of Silverstein that's a whole lot darker. Sue's father likes to drink and gets in a physical fight with his drag queen son. Then, the father essentially makes the kid his slave and caretaker. He ends his tale with, "And on nights that I can't score/Well, I can't tell you any more," implying that the father manipulates his son to sleep with him.