11 of the Most Wonderfully Weird Shel Silverstein Poems

Poetry is a natural part of most childhoods, from Dr. Seuss and Sesame Street to nursery rhymes and lullabies. But when I look back on the countless hours I spent sitting inside my closet and reading my heart out as a kid, there is one poet who especially stands out to me: Shel Silverstein. Don’t get me wrong, I love Dr. Seuss just as much as then next person—but ol' Shelly just always seemed to speak straight to my nerdy soul, and he still does.

Though Shel had a long and colorful career that included drawing cartoons for Playboy and writing songs for Johnny Cash, what I and most '90s kids remember are his extremely weird and wonderfully intriguing poetry collections, such as Where the Sidewalk Ends, Falling Up, and my personal favorite, A Light in the Attic.

Shel had a knack for blowing the minds of pre-adolescents around the world with his witty, ironic, absurd, humorous, and sometimes heartbreaking lines that never failed to rhyme. So, in celebration of his would-be 85th birthday, here’s a nostalgic look back at some of Shel's best work.

  1. "The Nailbiter"
    As a life-long nailbiter myself, this poem has always given me a certain kind of satisfaction. Just add this to the long list of ways that Shel just gets me.  
  2. "Homework Machine"
    Oh, the "Homework Machine." Every finals week throughout college, I would get out my old worn copy of A Light in the Attic and read this poem just to remind myself that even if such a thing existed, homework machines wouldn’t be as good as they might seem. Thanks, Shel.
  3. "Needles and Pins"
    A wisher and a dreamer at heart, I remember this poem fueling my wanderlust from a young age. I spent so many boring summer afternoons just wishing that someone like Shel would sweep me away to “anywhere new.”
  4. "Whatif"
    One of the things that Shel has always done best is personifying very abstract things—in this case, worrisome thoughts he called "whatifs." Not only did this poem validate the everyday worries of childhood (“Whatif I don’t grow taller?” and “Whatif my teeth don’t grow in straight?”), but it also turns these worries into things that kids are able to laugh at and overcome. 
  5. "Listen to the Mustn’ts"
    Just another bit of unconventional inspiration from Mr. Silverstein, this poem encourages children to break the rules and to challenge themselves in order to achieve their dreams. 
  6. "Hinges"
    I remember the drawing that accompanies this poem more than anything. (Who could forget it?) I was fascinated by the idea that thoughts and wishes could be tangible things just floating around in our heads, able to be plucked out and tossed aside whenever we pleased.
  7. "Backward Bill "
    Reminiscent of “opposite day,” Backward Bill always made me laugh. Aside from the catchy anecdote, this poem’s irony was something that I didn’t truly understand until I was much older. But that is the beauty of Shel’s work—it can still be appreciated decades after you first read it. 
  8. "Mr. Smeds and Mr. Spats"
    Sometimes Shel enjoyed being just downright silly. This poem’s illustration says it all.
  9. "Cloony The Clown"
    In light of the recent loss of great comedian Robin Williams to the cold grip of depression, this poem takes on new significance. I laughed right along at Cloony when I was a child, but now, this poem is so real and haunting that it brings tears to my eyes. 
  10. "One Inch Tall"
    Shel’s overactive imagination was so relatable as a child, which is what made poems like "One Inch Tall" so much fun to lose yourself in.
  11. "Happy Ending?"
    Concluding this list is a piece of wisdom from the man himself. Counteracting every fairy tale we’ve ever heard, Shel reminds us that endings—even good ones—are irrelevant when compared to the meaning of the rest of the story. I hope your start and middle were as unforgettable as your work is to me, Shel. Happy Birthday. 

(Featured image via Instagram)