week 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 mocked
mercilessly. After all, he had been
a subversive rebel since he prowled those same school corridors.
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.
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 I those
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.”
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
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.
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.
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
Silverstein was a character in many of his Playboy cartoons.
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.
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.”
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.
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.
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.
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.
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.
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.
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.
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.
Uncle Shelby’s ABZ Book for adults:
A Light in the Attic:
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....
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
“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.