11 of Shel Silverstein's Most Weird and Wonderful Poems

Like most kids, I heard poetry almost from the moment I popped out of the womb — in the lullabies and nursery rhymes my mom sang to me when putting me to bed, in Dr. Seuss books, and on Sesame Street. But when I think back on who really unlocked the power and potential of poetry for me, there's only one answer: Shel Silverstein.

Silverstein, born Sheldon Allan on Sept. 25 1930, had a long and varied career that involved working as a lead cartoonist for Playboy and writing songs for artists like Johnny Cash and Waylon Jennings. But for me (and millions of others who grew up in the latter part of the 20th century) he's the mad genius behind poetry collections like Where the Sidewalk Ends, A Light in the Attic, and Falling Up, as well as the classic children's story The Giving Tree.

I don't remember exactly when or how Silverstein's poetry came into my life. I do remember it blowing my pre-adolescent mind. Sure, some of the nursery rhymes I had been singing since infancy were a little dark, but the stuff in Where the Sidewalk Ends was on a whole different level — absurd and ironic, combining sharp wit, gross-out humor and heartbreaking pathos. Silverstein veered from the fanciful ("Melinda Mae") to the gentle and inspirational ("Hug O' War"). He captured the innocence of a child's imagination (WILL my finger get bitten off if I stick it too far up my nose?) without talking down to kids or being trite and sentimental. And those drawings! A self-trained illustrator, Silverstein had a visual style that was a lot like his writing — a little loose, a little sloppy, and completely indelible. What child could forget images like this?

So in honor of what would have been Silverstein's 84th birthday (he passed away in 1999), here's a look back at 11 of his funniest, weirdest, most inspiring and most memorable poems.

1. "Sick," Where the Sidewalk Ends

Before Ferris Bueller, there was Peggy Ann McKay, who couldn't go to school today because of two-page long list of (rhyming) ailments. What kid couldn't identify with Peggy Ann's creative and valiant (if misinformed) attempt to skip school? We secretly cataloged "instamatic flu" and "caved-in belly button" for our own personal future use.

2. "Whatif," A Light in the Attic

As someone whose anxious tendencies have only increased with age, this one hits just as hard now as it did then. Who hasn't had a nighttime (or daytime... or lunchtime... or any time) visit from the Whatifs? The questions range from the silly ("Whatif green hair grows on my chest?") to the devastating ("Whatif nobody likes me?") but the message was what mattered — being a kid doesn't mean you can't have legitimate worries and fears, and if you do, you're not alone.

3. "Where the Sidewalk Ends," Where the Sidewalk Ends

Admit it, after you saw the accompanying cartoon for this poem, you wanted to follow every road to its conclusion, in hopes of finding the mystical ledge, just so you could say you peered over the edge of the world.

4. "Smart," Where the Sidewalk Ends


Adding "Smart" to this list was a no-brainer — not only did it teach us the value of money, it taught us the wonders of irony as well. 

5. "The Loser," Where the Sidewalk Ends

There's no deep, meaningful message in "The Loser" (except maybe be careful with your valuables, lest they roll away), but this clever little poem (and it's accompanying wacked-out illustration) is as LOL-funny now as it was then.

6. "This Bridge," A Light in the Attic

Like so many of Silverstein's poems, "This Bridge" cuts two ways. Sure, it's inspiring, telling the reader that it's possible for him or her to go out into the world and see wondrous things, but the last line hints at the scary part of making big things happen in your life — you have to do it alone, no one else can do it for you.

7. "Needles and Pins," Falling Up

As a restless child with an overactive imagination, this poem spoke directly to the wanderlust in my heart. I spent a good chunk of my adolescence wishing for a captain and crew to "take me, oh take me/To anywhere new."

8. "It's Hot!," A Light in the Attic

With the sticky, humid days of summer still fresh in our minds, this delightfully demented poem rings loud and true. A common argument in the winter vs. summer debate is that you can always put more layers on, but there is only so much you can take off; Shel Silverstein begs to differ.

9. "Skin Stealer," A Light in the Attic

Silverstein's poems and illustrations were not so ghoulish that they gave me nightmares, but this one came pretty close. Unzipped skin, unscrewed heads, and that cycloptic coo-coo with his creepy grin definitely sent some shivers down my spine.

10. "Listen to the Mustn'ts," Where the Sidewalk Ends

These eight lines pretty much sum up everything that Shel Silverstein and his children's poetry are about — throwing off conventionality and negativity, and embracing the power of imagination and possibility. It's not just a great message for kids — it's a great message for everyone. 

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