Sly and Subversive Children's Poet Shel Silverstien--National Poetry Month 2026

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  

What Bill Mauldin and Willie and Joe Taught a Boy From Cheyenne

 

                Sgt. Bill Mauldin on the job in Italy covering the war from the front lines for Stars and Stripes.  He looked younger than his 22 years.

When I was a boy I was obsessed with the great event of my parents’ lifetime—World War II.  It was hard not to be.  Almost every house I ever visited had at least one framed photo of a handsome young man in uniform proudly displayed.  Sometimes more.  Husbands, brothers, fathers.  Most came home.  Some did not.

The survivors of those photos were still mostly youngish men in the prime of their lives—my father and the fathers of almost all my friends.  They were serious, hard working men.  They were very busy doing things, sometimes big things.  To a man those I knew best, my father and uncles, could hardly be made to talk about their experiences.  If pressed they would say, “Well, I was in Europe for a while.”  Or “I was a Seabee.”  Further details were seldom forthcoming.

They belonged to the Legion or the VFW, but seemed neither super-patriotic nor querulously eager for the next war.  They took comfort in being around other men who had been there, but they distrusted the occasional braggart and blowhard at the bar.  Their contempt for that ilk was summed up years later in a Bill Mauldin cartoon in the Chicago Sun Times showing one of the bellicose Legion leaders of the Vietnam era beginning and ending his World War II service, “folding blankets in Texas.”

For real information on what our dads did in the war, we had to turn to our mothers.  Mine was glad to share her meticulously kept scrap books with photos, postcards, newspaper clipping, maps, V-mail letters, and even un-used ration stamps.  And she dug out the long buried footlocker in the basement chocked full interesting stuff.  I claimed a khaki overseas cap, which for a season or two I wore everyday in lieu of my customary cowboy hat, a web belt, canteen, mess kit, ammo pouches, a gas mask bag, and a helmet liner.  I was outfitted well for the endless games of war the neighborhood boys played in backyards among hedges and window wells.

On Sunday afternoons I was glued to the TV documentaries about the war that were still a staple of the air—the Army’s The Big Picture, Victory at Sea, Silent Service, and most episodes of Walter Cronkite’s The Twentieth Century.  And then there were the old movies that played on the daily movie matinee show which came on just as I got home from school.  I thought I knew what war was about.

 

Finding a well-thumbed copy of Mauldin's Up Front was an eye-opener for World War II teen fan boy in Cheyenne,  So was Ernie Pile's collected columns in This is Your War.

But of course, I didn’t know squat.  Until I found in my mother’s bookshelves well-thumbed editions of This is Your War, a collection of columns by the great war correspondent Ernie Pyle and a couple of collections of Bill Mauldin’s Willie and Joe cartoons for Stars and Stripes.

Both Pyle and Mauldin rose to fame covering the brutal, unglamorous Italian campaign as troops slogged slowly north through the Boot against stubborn German resistance, treacherous mountainous terrain, rubble strewn street fighting, supply shortages, and often incompetent leadership.  So much for Winston Churchill’s “soft underbelly of Europe.”  Fighting there dragged on after it was relegated to a side show and Allied troops, liberated at last from the Normandy beaches, were racing across France far to the north.

Both men talked about the war from the front line perspective of the G.I. dogface—exhausted, bitter, cynical, stripped of all illusions of glory, immune to patriotic exhortations, and suffering as much at the hands of clueless generals and idiot second lieutenants as from the usually unseen Nazis.  Pyle drew the picture with words.  Mauldin just drew the picture.

And remarkably, he did so in the official GI newspaper Stars and Stripes as a sergeant in the Army he chronicled.  Willie and Joe were his creation to represent the lives of the grunts on the ground.  They were unshaven, slovenly, and perpetually exhausted.  They looked in those drawings like old men.  But Mauldin, who was only 22 and looked years younger, pointed out that Willie and Joe were the same age he was.  War did that to them.

The old spit-and-polish brass hated Mauldin and often tried to get him banned from the paper or refused to issue passes to their front line units—where he went anyway, regardless of any stinking passes.  General George Patton called him to his headquarters and threatened to have him arrested for disturbing morale.  Dwight Eisenhower had to personally intercede with orders to leave Mauldin alone.  He thought the comics helped his men “let off steam.”

Stuff like this jab a Old Blood and Guts got Mauldin personally called on the carpet by George Patton.  General Eisenhower had to personally intervene to keep him out of trouble and in print.

Mauldin was born on October 29, 1921 in Mountain Park, New Mexico.  His family were no strangers to the military.  His grandfather was a cavalry scout in the campaigns against the Apache.  His father was an artilleryman in World War I.

The family moved to Phoenix, Arizona where Mauldin finished high school and became interested in art.  He enlisted in the Arizona National Guard, but was able to go to Illinois where he attended classes at Ruth VanSickle Ford’s Chicago Academy of Fine Art.

He never completed his studies.  He was called up from the Guard to active duty in 1940.  He was assigned to the 45th Division, the first all-Guard unit activated prior to America’s entry into the war and made up units from New Mexico, Arizona, Colorado, and Oklahoma including many Native Americans.

Mauldin was a good soldier despite his almost childish appearance.  He advanced to the rank of sergeant quickly and began contributing cartoons to the Division newspaper.  While still training stateside he created Willie and Joe, based on his best friend and himself.  When the unit deployed overseas he was assigned to the Division Press Office.  He did not consider that to be behind the lines duty.

When the Division landed in Sicily in July of 1943 for its first combat operations, Mauldin was right there with the front line infantry.  He stayed there.  He was with them again on September 10 when the Division landed at Agropoli and Paestum, the southernmost beachheads of the Salerno campaign.  Thus began the long, grinding inch-by-inch slog up the length of the Italian Boot.

Mauldin’s cartoons were being reprinted in Stars and Stripes and in February 1944 he was transferred to the Army newspaper, issued a Jeep and given nearly a carte blanche to cover the front as he thought best.  His reputation among GIs was high and everywhere he went they welcomed him even if officers were usually mortified.  Recognition that he often took the same risks as infantrymen won him credibility, especially after he was wounded by mortar fire while visiting a machine gun crew near Monte Cassino.

 

                                 Bogged down hopelessly in Italy, Willie and Joe were a tad cynical about all of the glory of D-Day.

He returned to the front and his drawings, which were now also being circulated by the Army to civilian papers in the States.  The Brass felt that the cartoons would make clear to the public the realities of the war and explain the slow pace of advance in Italy to a public which expected quick victories.

Mauldin was awarded the Legion of Merit, an award usually given to field grade officers in combat operations.  At the end of European operations, Mauldin wanted to have Willie and Joe killed on the last day of combat, a final thumb of the nose to the futility of war.  The horrified Brass quickly nixed that idea.

Back in the States and out of the service, Mauldin found himself something of a celebrity.  He had even made the cover of Time.  He won the Pulitzer Prize in 1945.  His first book Up Front, one of the books I purloined from my mother’s selves, was a best seller.  It contained many of the best Willie and Joe cartoons along with no-holds-barred essays that stripped all glory from war.

A defiant liberal, Mauldin found it difficult to fit into an America in the throes of Red Scare paranoia and hardening conservatism.  His attempts to establish a career as an editorial cartoonist were stymied as newspapers shied away from controversial content especially when he echoed the views of the American Civil Liberties Union and its opposition to witch hunts, blacklists, and attacks on individuals for their political opinions.

Willie and Joe had a hard time adjusting to civilian life back home.  Work was hard to find, their relationships broken or strained, and uncomfortable in the emerging post-war red scare.  In this panel Mauldin took a swipe at hardening racial and religious attitudes.  

He tried to transition Willie and Joe to civilian life and chronicled the hard times they had fitting in.  The public wasn’t interested.

Discouraged, Mauldin turned to illustrating magazine articles and books.  He even tried his hand at acting, appearing with another youthful looking veteran, Audie Murphy in the Civil War film, The Red Badge of Courage.

Mauldin starred with another young vet, Audie Murphy who was the most decorated soldier of World War II, in John Huston's adaptation of Stephen Crane's The Red Badge of Courage.

Mauldin also struggled with his personal life.  He married three times and fathered eight children.

In 1956 at the height of the Cold War Mauldin ran for Congress in a rural Upstate New York District as a peace Democrat.  He campaigned hard and was personally well received by local farmers—until his foreign policy positions failed to match to staunch conservatism of the district.

 

Liberal Bill Mauldin was not a good fit for the conservative, anti-Communist Up State New York Congressional District in his 1948 run for Congress.

In 1958 he finally got steady work as staff editorial cartoonist for the Saint Louis Post-Dispatch and the national syndication that went with it.  Ironically, Mauldin’s still struggling career got a boost when he won a second Pulitzer Prize 1n 1959 for a cartoon that was acceptable to the anti-Communist crowd.  It pictured Boris Pasternak, author of Dr Zhivago in a Soviet Gulag asking a fellow inmate, “I won the Nobel Prize for Literature. What was your crime?”  In fact, the cartoon was in line with Mauldin’s consistent defense of the rights of free speech and civil liberties.

Mauldin moved in 1962 to the Chicago Sun-Times, Marshal Field’s liberal challenger to Col. Robert McCormick’s hyper-conservative Chicago Tribune.  It gave him a supportive home for outstanding political cartooning for the rest of his career.  Mauldin’s editorial page panel was one of the big reasons I became a dedicated reader of that paper for years.

Among his famous Sun-Times cartoons is the picture of Lincoln seated in the Lincoln Memorial burring his face in his hands the day after the assassination of John F. Kennedy—which inexplicably failed to win a third Pulitzer.    He was a bitter opponent of the Vietnam War and supporter of anti-war protesters.  His cartoons during and after the Democratic Convention in Chicago in 1968 featured Mayor Richard J. Dailey as a Keystone Kop, which made Hizonor apoplectic.

Mauldin's depiction of Mayor Daley as a Keystone cop during and after the 1968 Democratic National Convention enraged undisputed Boss of Chicago politics.  He also took swipes at the Chicago press and media, including his own Sun-Times, for their often fawning coverage of Hizzoner as the master of the "city that works."

Mauldin retired in 1991.  He was missed.  He occasionally contributed a cartoon and did several interviews.  He entertained old friends and admirers.

But his fine, sharp mind was fading.  Suffering from Alzheimer’s Disease Mauldin was badly scalded in bathtub accident and died in great pain in Newport Beach, California on January 11, 2002.  He was buried with so many of his fallen comrades at Arlington National Cemetery.

Willie and Joe endure.

These days it is hard not to imagine Bill Mauldin as one of the original Antifa and wonder how he would skewer and enrage our would-be tinpot dictator.