A Shel Silverstein Forever Stamp was unveiled at a ceremony at Darwin Elementary in Chicago's Logan Square neighborhood in 2022.
In April 2022 the United States Postal Service unveiled a new First Class Forever Stamp honoring beloved children’s poet Shel Silverstein at the Chicago elementary school he attended as child. My friend Mike Gold, former Chicago Seed staffer, pop culture commentator, and comic book maven described the event as “Honoring the most subversive folkie I’ve known” adding, “this is stupidly cool, but I do not believe these folks did their vetting.” That was especially true of the earnest school official who also unveiled a mural honoring the alumnus and spoke in the kind of uplifting platitudes that Shel would have mocked mercilessly. After all, he had been a subversive rebel since he prowled those same school corridors.
Silverstein was an almost entirely self-taught artistic polymath—writer, poet, cartoonist, singer, songwriter, and playwright. He brought his own quirky, irreverent, and off-center viewpoint to all of these efforts.
He was born in Chicago to a Jewish family on September 25, 1930 and raised in the Logan Square neighborhood. A social misfit—we’d call him a nerd today—he attended Darwin Elementary and Roosevelt High School. He described his development those days:
When I was a kid—12 to 14, I’d much rather have been a good baseball player or a hit with the girls, but I couldn’t play ball. I couldn’t dance. Luckily, the girls didn’t want me. Not much I could do about that. So, I started to draw and to write. I was also lucky that I didn’t have anybody to copy, be impressed by. I had developed my own style; I was creating before I knew there was a Thurber, a Benchley, a Price and a Steinberg. I never saw their work ‘til I was around 30. By the time I got to where I was attracting girls, I was already into work, and it was more important to me. Not that I wouldn’t rather make love, but the work has become a habit.”
He did not, however, become a monk to his work. The girls and women would buzz around his uniqueness as an adult and he became kind of a Satyr sleeping with hundreds of women in a chain of casual relationships. He became a poster boy of Beat generation sexual rebellion, and the post-Pill sexual revolution of the 1960’s.
Silverstein with his guitar.
Silverstein briefly attended—and was expelled—from the University of Illinois and briefly attended the Chicago Academy of Fine Arts and Roosevelt University, where his first cartoons were published in The Torch before he was drafted. He was not entirely disappointed. He came to believe that college was a waste for him and that he would have been better served traveling and experiencing the World.
The Army posted him to Japan and Korea in a non-combat role on the staff of Pacific Stars and Stripes. Assigned to lay-out and design, he began to submit cartoons to fill empty space and eventually got a regular series, Take Ten. The paper published a collection under that title in 1955. After his discharge Ballantine Books issued a mass market paperback of the cartoons as Grab Your Socks in 1956. The new edition included an introduction by another former Stars and Stripes cartoonist Bill Mauldin. The book was a success and marked the real beginning of his career.
Ballantine Books published Silverstein's 1956 collection of cartoons from Pacific Stars and Stripes, foreword by Bill Mauldin.
The book led to steady employment by hometown entrepreneur Hugh Heffner. In 1957 he became one of the lead cartoonists for Playboy. Hef soon also noted Silverstein’s writing talent and his itch for travel and adventure inspired by Jack Kerouac and On the Road. He was given his own regular feature, Shel Silverstein Visits...witty first-person travel pieces illustrated with images of himself. His bald/shaved head and full black beard quickly made him a recognizable celebrity. The series took him to off-beat and hip destinations—a New Jersey nudist community, the Chicago White Sox training camp, San Francisco’s Haight-Ashbury, Gay Mecca Fire Island, Mexico, Swinging London, Paris of mademoiselles and posing existentialist intellectuals, Hemingway’s old stomping grounds in Spain and Africa, and an Alpine Swiss village.
Silverstein was a character in many of his Playboy cartoons.
Another Playboy feature was expanded into Uncle Shelby’s ABZ Book in 1961, his first book of new, original material. The adult alphabet book let him to being practically drafted into writing for children. He explained it: “I never planned to write or draw for kids. It was…a friend of mine, who insisted—practically dragged me, kicking and screaming, into [Harper & Row editor] Ursula Nordstrom’s office. And she convinced me that Tomi was right; I could do children’s books.
His relationship with Nordstrom was fruitful largely because she understood the boundaries Silverstein demanded of his editors. Asked if he would change something he had produced on an editor’s say-so, he answered with a flat “No.” But he added: “Oh, I will take a suggestion for revision. I do eliminate certain things when I’m writing for children if I think only an adult will get the idea. Then I drop it, or save it. But editors messing with content? No.”
The result were a remarkable run of illustrated children’s books beginning with Uncle Shelby’s Story of Lafcadio: The Lion Who Shot Back in 1963 followed by instant classics like the poignant fable The Giving Tree in 1964, his first collection of poems Where the Sidewalk Ends in 1974, and A Light in the Attic written after the tragic death of his 11 year-old daughter Shoshanna Jordan Hastings and dedicated to her in 1981.
Where the Sidewalk Ends was an instant classic.
All during these years he was also dabbling in music and composing or co-writing songs in many genres. He began appearing in smoky folk clubs in New York’s Greenwich Village and back in Chicago. He made many friends with whom he collaborated and/or wrote songs for including Clancy Brothers and Tommy Makem, Dr. Hook, Johnny Cash, and Chicago’s Steve Goodman. Silverstein’s debut album was Hairy Jazz in 1959, Inside Folk Songs in 1962 during the popular folk revival, the racy Shel Silverstein’s Stag Party in 1963, I’m So Good That I Don’t Have to Brag in 1965, and Boy Named Sue and Other Country Songs in 1969. He also did film soundtracks including Ned Kelly in 1970 and Who Is Harry Kellerman and Why Is He Saying Those Terrible Things About Me? in ’71.
Among Silverstein’s best known songs are several for Dr. Hook and the Medicine Show—On the Cover of the Rolling Stone, Freakin’ at the Freakers’ Ball, Sylvia’s Mother, and The Ballad of Lucy Jordan also covered by Marianne Faithfull. Loretta Lynn had country chart toppers with One’s on the Way and Hey Loretta. Judy Collins recorded the poignant Civil War ballad and the more raucous Hey Nelly Nelly. The Irish Rovers had a hit with the pub sing-along The Unicorn. Johnny Cash did 25 Minutes to Go about a man on death row with each line counting down one minute closer to his end and had his biggest single ever with A Boy Named Sue.
Silverstein on The Johnny Cash Show in a duet of A Boy Named Sue.
Beginning in 1959 Silverstein also began writing for the theater with Look, Charlie: A Short History of the Pratfall, a chaotic off-Broadway comedy in collaboration with Jean Shepherd and Herb Gardner at New York’s Orpheum Theatre. He went on to pen more than 100 one act plays and skits which were produced in a variety of settings and venues. On television he co-wrote Things Change, is a 1988 comedy/drama with David Mamet and starring Joe Mantegna and Don Ameche.
In addition to Chicago and Greenwich Village, Silverstein lived on a houseboat in Sausalito, California from 1967-’75. He also owned homes on Martha’s Vineyard and Key West, Florida. He also spent time in the Chicago and California Playboy Mansions where he cavorted with Bunnies, Playmates, and other guests.
He never married although he had hundreds of affairs. He met Susan Taylor Hastings at the Playboy Mansion and lived with her in Sausalito. The had daughter Shoshanna in 1970 but Taylor died two days before the girl’s 5th birthday. The girl was sent to live with relatives but died of a brain aneurism at age 11. Later in Key West he met Sarah Spencer, who drove a tourist train and they had a son Matthew De Ver on November 10, 1984, who later became a New York City–based songwriter and producer.
Silverstein’s last album in 1998, Old Dogs, was a two-volume set with country stars and old pals Waylon Jennings, Mel Tillis, Bobby Bare, and Jerry Reed.
On May 10, 1999, Silverstein died at age 68 of a heart attack at his home in Key West. He was buried at Westlawn Cemetery in Norridge, Illinois.
Silverstein believed that written works needed to be read on paper—the correct paper for the particular work. He usually would not allow his poems and stories to be published unless he could choose the font size and color, and quality of the paper.
From Uncle Shelby’s ABZ Book for adults:
From A Light in the Attic:
Many consider this Silverstein’s masterpiece.
The Giving Tree
Once there was a tree....
and she loved a little boy.
And everyday the boy would come
and he would gather her leaves
and make them into crowns
and play king of the forest.
He would climb up her trunk
and swing from her branches
and eat apples.
And they would play hide-and-go-seek.
And when he was tired,
he would sleep in her shade.
And the boy loved the tree....
very much.
And the tree was happy.
But time went by.
And the boy grew older.
And the tree was often alone.
Then one day the boy came to the tree
and the tree said, “Come, Boy, come and
climb up my trunk and swing from my
branches and eat apples and play in my
shade and be happy.”
“I am too big to climb and play” said
the boy.
“I want to buy things and have fun.
I want some money?”
“I’m sorry,” said the tree, “but I
have no money.
I have only leaves and apples.
Take my apples, Boy, and sell them in
the city. Then you will have money and
you will be happy.”
And so the boy climbed up the
tree and gathered her apples
and carried them away.
And the tree was happy.
But the boy stayed away for a long time....
and the tree was sad.
And then one day the boy came back
and the tree shook with joy
and she said, “Come, Boy, climb up my trunk
and swing from my branches and be happy.”
“I am too busy to climb trees,” said the boy.
“I want a house to keep me warm,” he said.
“I want a wife and I want children,
and so I need a house.
Can you give me a house ?”
“I have no house,” said the tree.
“The forest is my house,
but you may cut off
my branches and build a
house. Then you will be happy.”
And so the boy cut off her branches
and carried them away
to build his house.
And the tree was happy.
But the boy stayed away for a long time.
And when he came back,
the tree was so happy
she could hardly speak.
“Come, Boy,” she whispered,
“come and play.”
“I am too old and sad to play,”
said the boy.
“I want a boat that will
take me far away from here.
Can you give me a boat?”
“Cut down my trunk
and make a boat,” said the tree.
“Then you can sail away...
and be happy.”
And so the boy cut down her trunk
and made a boat and sailed away.
And the tree was happy
... but not really.
And after a long time
the boy came back again.
“I am sorry, Boy,”
said the tree, “but I have nothing
left to give you—a
My apples are gone.”
“My teeth are too weak
for apples,” said the boy.
“My branches are gone,”
said the tree. “You
cannot swing on them—”
“I am too old to swing
on branches,” said the boy.
“My trunk is gone,” said the tree.
“You cannot climb— ”
“I am too tired to climb” said the boy.
“I am sorry,” sighed the tree.
“I wish that I could give you something....
but I have nothing left.
I am just an old stump.
I am sorry....”
“I don't need very much now,” said the boy.
“just a quiet place to sit and rest.
I am very tired.”
“Well,” said the tree, straightening
herself up as much as she could,
“well, an old stump is good for sitting and resting
Come, Boy, sit down. Sit down and rest.”
And the boy did.
And the tree was happy.
—Shel Silverstein
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