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19 Creepy Meanings Behind Shel Silverstein Poems and Stories

Considering his colorful life, it makes sense that there are some dark Shel Silverstein poem meanings, as well as some deeply witty and intentionally creepy Shel Silverstein stories. The man was certainly offbeat, if not extraordinary. He was unflinching and one of the most relatable children’s writers in the world. 

Silverstein lived a far-from traditional life. He wrote some pretty raw songs, illustrated cartoons for Playboy, hung out with Hugh Hefner, and allegedly slept with hundreds of women. He never married but had two children with a former Playmate. Tragically, he lost his 11-year-old daughter to a brain aneurysm. 

The meanings behind Shel Silverstein poems and stories are debated to this day, but it’s undeniable that some were inspired by his weird and complex life. Are Silverstein’s poems and stories a safe place to dream, ponder extreme possibilities, and question the morals of society? Or was he promoting drug use, cannibalism, disrespect for authority, violence, anarchy, and the occult?  

Let’s put it to a vote. Which of these Silverstein stories or poems strike you as the creepiest?

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