Remembering The Multi-Talented Shel Silverstein

Like The Giving Tree, his art continuously gives and gives even long after he’s gone.

Shel Silverstein’s poems and stories are essential reads for children and adults alike. They paint a simple yet beautiful picture of morality with both words and illustrations. Even 20 years after his passing Silverstein’s books are found in almost 50 different languages and countless schoolrooms.

The Giving Tree Cartoon 1973 by Shel Silverstein

But the beatnik artist was far more than just an author.

Born in 1930, Silverstein grew up in Chicago where he was constantly writing and drawing. He was expelled from the University of Illinois for poor grades, then enrolled in Chicago Academy of Fine Arts, but was drafted into the U.S. Army in 1953, serving in Korea and Japan. His wife Susan Hastings died in 1975 and their daughter Shoshana died in 1982, one day before her fifth birthday. He eventually remarried in the 1980s and had a son.

While serving, Silverstein was a journalist and cartoonist for the Pacific Stars and Stripes, a military newspaper. His drawings in the publication were usually Army-centric, but kept lighthearted. He was almost court-martialed after drawing a comic strip about officers dressing their families with stolen uniforms.

After his discharge from the Army, Silverstein became a leading cartoonist for Playboy Magazine. In 1963 he published his first children’s book, Uncle Shelby’s Story of Lafcadio, the Lion Who Shot Back. And then he taught himself guitar.

Silverstein wrote more than 800 songs, including a few surprise hits. He wrote “A Boy Named Sue” for Johnny Cash and won a Grammy. His song “I’m Checkin’ Out” was nominated for both an Oscar and Golden Globe after Meryl Streep performed it in the film Postcards from the Edge. And Silverstein won another Grammy for the album Where the Sidewalk Ends, which was a musical version of his book of poems with the same name.

Meryl Streep singing “I’m Checkin’ Out”

He also wrote and co-wrote hit plays like The Lady or the Tiger, The Devil and Billy Markham and Oh, Hell! in the 1980s. He even co-wrote a film with David Mamet in 1988 called Things Change.

But Silverstein will always best remembered for his satirical yet heartbreaking books like The Giving Tree and The Missing Piece, along with his book of poems Falling Up, Where The Sidewalk Ends and A Light In the Attic. The words and images from these books continue to inspire children and adults two decades after his death—exactly as he would’ve hoped. As Silverstein writes in his poem When I Am Gone:

“When I am gone what will you do?
Who will write and draw for you?
Someone smarter—someone new?
Someone better—maybe YOU!”