Watch Shel Silverstein, The Most Interesting Children’s Author In The World, Perform “A Boy Named Sue” With Johnny Cash

Johnny Cash country music

The late Shel Silverstein is not just the most interesting children’s author in the world: he may be the most interesting man in the world.

I grew up reading his children’s poetry books like “The Giving Tree” and “Where the Sidewalk Ends,” and having nightmares about the terrifying photos of him on the back covers of those books.

But, when he wasn’t writing bizarre, memorable poetry for kids or staring into your soul through a photograph, he was living a sex-filled, celebrity lifestyle at the Playboy Mansion and writing songs for some of country music’s biggest stars.

And my childhood reading list just got a whole lot more interesting.

According to Ozy, Silverstein began his career as a cartoonist for the fledgling Playboy Magazine. His success and popularity there made him a frequent and popular guest at the Playboy Mansion, where he lived for weeks or months at a time.

According to his biography, A Boy Named Shel by Lisa Rogak, he slept with “hundreds, perhaps thousands of women through the years.” In fact, many believe that Shel wrote many of his children’s poems under Hugh Hefner’s infamous roof, to the chagrin of my mom and every elementary school librarian who might rather not know about the exploits of the man behind their children’s bedtime reading.

But the prolific (with words and women) Silverstein didn’t stop at children’s poetry and wooing Playboy bunnies: he was also a highly popular country songwriter.

He wrote charting songs for Brenda Lee, Bobby Bare, Loretta Lynn, Jerry Lee Lewis, and Waylon Jennings, among many others on his way to his posthumous induction into the Nashville Songwriter’s Hall of Fame in 2002. But his most famous song, “A Boy Named Sue” earned Silverstein a Grammy Award in 1970 for Best Country Song, and earned Johnny Cash the Grammy for Best Male Country Performance. 

In his appearance on “The Johnny Cash Show,” Silverstein and the Man in Black performed part of the song together. And while Shel’s shrill, gravelly vocals were a little shocking opposite Cash’s iconic baritone, you can’t deny the man’s talent. 

Shel Silverstein on The Johnny Cash Show:

I re-read portions of Shel’s (in his words) “weird children’s books” recently, and I was shocked at how many of them I remembered. His simple drawings combined with mesmerizing and outlandish verse are stuck in my brain, much like the image of a deadbeat dad fighting his son named “Sue” outside a bar, “kicking and a-gouging in the mud and the blood and the beer.”

If you’re in the mood for some nostalgia, pick up some classic Shel Silverstein books at the library and leaf through some of your childhood memories.

And this time, think of Shel writing those silly poems while lounging at the Playboy Mansion, surrounded by half-naked women, with Johnny Cash or Kris Kristofferson on the phone.

What a life.

“A Boy Named Sue” live at San Quentin:

A beer bottle on a dock



A beer bottle on a dock