On This Day in 1999, We Lost the Singer-Songwriter, Poet, and Cartoonist Behind Johnny Cash’s Best-Known Whimsical Hit

Shel Silverstein is known by one generation as an excellent Grammy Award-winning singer-songwriter who wrote songs for the likes of Johnny Cash, Tompall Glaser, Marianne Faithfull, and others. To another generation, he’s the man who wrote and illustrated countless children’s books, from The Giving Tree from 1964 to Where The Sidewalk Ends from 1974. 

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He’s a legend and was a particularly complicated man with his own vices, but his legacy lives on today in a positive light. And, tragically, on May 10, 1999, Silverstein passed away at the age of 68. Let’s look back at his career in music, specifically, to honor the legend himself.

The Legacy of Shel Silverstein

Shel Silverstein was born in Chicago, Illinois, on September 25, 1930. He spent much of his time between Chicago and Kenosha, Wisconsin, throughout his childhood, both of which are referenced in several of his books. 

Throughout his life, Silverstein was known for being eccentric. He lived in a houseboat in California in the late 1960s. He was also known for his sexual proclivities and was a frequent visitor to the Playboy Mansion. That’s not exactly what you’d expect from a famed children’s book author. But Silverstein never actually planned to become a children’s book author, according to the man himself.

“I never planned to write or draw for kids,” Silverstein once said in a 1975 interview. “It was Tomi Ungerer, a friend of mine, who insisted—practically dragged me, kicking and screaming, into Ursula Nordstrom’s office. And she convinced me that Tomi was right; I could do children’s books.”

Silverstein, the Songwriter

And while Silverstein is known by many as a children’s book author, he was also an accomplished songwriter. He recorded quite a few albums of both music and poetry over the years, starting with the 1959 recording Hairy Jazz.

Silverstein most notably wrote the 1969 classic “A Boy Named Sue”, made famous by Johnny Cash. That song earned Silverstein a Grammy Award in 1970. He also wrote the tune “I’m Checkin’ Out” for the film Postcards From The Edge, performed by Meryl Streep and Blue Rodeo. That song earned him nominations for the Academy Awards and Golden Globe Awards. 

In 2002, Silverstein was posthumously inducted into the Nashville Songwriters Hall of Fame.

While not technically music, Silverstein did record “Where The Sidewalk Ends”, a collection of poetry, on cassette in 1983. His friend and producer Ron Haffkine also worked on the song. It would later earn a Grammy Award for Best Recording for Children in 1984. 

Shel Silverstein passed away on this day in 1999 at the age of 68, following a series of heart attacks. His books carry his memory forward, as well as the beautiful music he made.

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