Shel Silverstein

Shel Silverstein

1930-1999

DJ Name: Shakin’ Shel

This week in Jewish holiday celebrations is Rosh Hashanah. On September 18, the Jewish community will ring in its New Year and celebrate God’s creation of this world. The celebration spans over 10 days and culminates with Yom Kippur, the holiest of holy days in the Jewish faith. In honor of the upcoming celebration, period of reflection and an abundance of challah, we wanted to highlight a historic Jewish dude who changed the way kids (and, honestly, adults) read and enjoy poetry forever with well-known works like The Giving Tree, A Giraffe and a Half and Where the Sidewalk Ends. That’s right! You guessed it! We’re talking about the inspirational, uplifting and kid-friendly Edgar Allen Poe! 

Lol, gotcha! That’s not right. Okay, moving on.  

So, it was actually Shel Silverstein who wrote The Giving Tree, A Giraffe and a Half and Where the Sidewalk Ends — along with many more works — not Edgar Allen Poe. Silverstein is our shuffler this week, and unknown to all except those who read HistoricShuffle.com, he* created this playlist of his favorite modern day hits for us, his favorite fans (*his ghost): 

A boy named Sheldon Allan Silverstein was born on September 25, 1930, during the Great Depression in Chitown. His father, Nathan, was a first-generation, Jewish immigrant from Russia who tied the knot with Helen Balkany of Cook County, Illinois iin 1926 — the year famous Chicago gangster, Al Capone, disappeared from the city streets and went into hiding for 3 months. Safe to say, that was probably a good time to get married. The Silverstein squad lived together in a place where the sidewalk ended and the street began, and there the sun burned crimson bright into their Humboldt Park apartment that they shared with their extended family — AKA Helen’s mother, AKA Shel’s g’maw and Nathan’s mother-in-law. It was a bit of a chaotic household — overflowing with noise and, probably, people. But it’s what they could afford considering they were living through the Big Ol’ Depression. 

Nathan owned a bakery with his bro, Jack. Every morning as Nathan departed for work, he told Shel and the whole fam, “I’m off to get this bread.” The daily dough (those dolla dolla bills) were in fact quite hard for the Silverstein Brothers to get because of the failing economy. People just weren’t buying baked goods, but the Silverstein Brothers still decided to expand their bakery. They bought a bigger space and rebranded their shop name to the Service Cake Company

With purchase of a larger space came the need to pinch more pennies. Oftentimes, they ate day-old bread and pastries for dinner. There were no silver spoons in sight for the Silversteins, especially after his sister, Peggy, was born. One more mouth to feed meant fewer food for all. As a way to escape the literal overcrowded element of his home and to find a place of his own, Shel turned to his comic books and the radio. He flipped through pages upon pages of adventure, and stations upon stations of his preferred genre, country music. The stories he read and lyrics he heard took him anywhere and everywhere throughout his childhood to places other than a cramped Chicago apartment filled with a stressed family. 

It took some time, but the bakery survived and eventually thrived so much that the Silversteins were able to move out on their own. As a boy, Shel attended Charles R. Darwin Elementary School where he doodled his way through classes and day dreamed of hitting a home run as a member of the Chicago White Sox alongside teammates like Luke Appling and Ted Lyons. Sadly for Shel, he struck out when it came to sports — especially his beloved baseball — he was very unathletic on and off the field. So he stuck to writing and drawing, which required no athletic ability. His teachers were not pleased when he’d turn in a cartoon drawing instead of his math homework. He continued his cartooning ways all the way through college — rumor has it, he was expelled because instead of a term paper, he turned in a caricature of his professor. (Don’t take our word for it. We are the rumor starters).

In addition to his teachers, Shel’s artistic endeavors were not supported by his father. Nathan called his doodles garbage (harsh) and thought he was throwing away his life by pursuing art. Dad Silverstein wanted his Shelly boy to take over the family bakery business. “Visualize it now, son: Baked by Shel Silverstein.” We guess the idea of baking didn’t appeal to Shel. Or perhaps his definition of “baked” was different from his father’s? Regardless, Nathan and Shel had their differences and Shel didn’t take over the family business. He had his own, “No, Dad, I’m not throwing away my life. I’m throwing away yours” moment and moved forward with his creative endeavors in writing and drawing, which actually kept him busy as he blocked out his haters AKA teachers and Dad. Later in life, he encouraged his kiddo (and adult) readers with the wise words in his poem “The Voice”:

There is a voice inside of you

that whispers all day long,

‘I feel that this is right for me,

I know that this is wrong.’

No teacher, preacher, parent, friend

or wise man can decide

what’s right for you – just listen to

the voice that speaks inside.

Are you feeling nostalgic? Because, same. 

So back to (non-virtual) school: Shel really was expelled from the University of Illinois for poor grades after a year and went on to study at the Chicago Academy of Fine Arts. Unfortunately, he only lasted a year there. Shel eventually found his place at Roosevelt University where he studied English and put his talents for doodles and words together as a contributing author to the school paper called The Roosevelt Torch. These not yet kid friendly cartoons were satirical takes on school policies like no smoking in class. However his time with the Torch was cut short. He was drafted by the Army in 1953 to serve in Japan and Korea during the Korean War. 

Turned out that Shel’s strongest weapon was actually his pen. He drew and wrote cartoons for the military newspaper, Stars and Stripes. His cartoons entertained his fellow troops while challenging the censor system. These were eventually compiled and published in his first book, Take Ten. After his stint in the war, Shel returned to Chicago and continued his writing pursuits. He wrote for publications like Look, Sports Illustrated and This Week. But every starving artist/writer needs a side hustle, and his was selling hot dogs at Chicago ballparks. Though there were no ifs, ands or “bunts” (ha, baseball puns) about his unfortunate athletic ability, the man made a mean hotdog and got to be right where he loved: near the ballpark, cheering on his White Sox and talking #sports with fellow fans of the game and about his #1 team. 

By 1957, Shel’s cartoonist career had begun to really balloon. He took his provocative cartoons to Playboy (kid friendly!), where he embarked on a long friendship with none other than Hugh Hefner — a huge advocate for kid friendly content, are we right?! He was a leading contributor to Playboy, and he also got to travel all over the world documenting far-flung places — from a Chicago White Sox training camp to Fire Island to a Swiss village where no one yodeled — in his series “Shel Silverstein Visits…”. Another book came for Shel in 1961, which was an elongated version of one of his Playboy features, called “Uncle Shelby’s ABZ Book.” Perhaps because of the name, or maybe because of his child-like cartoons, people were unsure if it was for kids. It most certainly was not for kids. The book is a satirical and cynical take on the archetypal children’s alphabet book and was not best suited for wee innocent minds, but hey, Shel said, the youth and the elderly should be treated the same as everyone else. 

While Shel found moderate success — and disdain — among his adult audience, his editors pushed him to enter the children-book-writing field. Mommy and Daddy wanted questionably provocative stories for their kiddos, and Shel needed to be the one to deliver, obviously. His editors said, “Shel, shoot your shot.” So Shel gave us The Giving Tree. And Where the Sidewalk Ends. And Falling Up. Because he’s a boss who can cross generational divides with his wit and dope drawing skillz. 

But Shel wore several creative hats, and refused to be only a children’s book writer, or only an adult satirical writer, or only a Playboy boy. He dipped his toes in music, too, and penned the Johnny Cash song “A Boy Named Sue” in 1969, which won him a Grammy. Shel wrote a bunch of other songs, too, but they’re not as cool or famous as “A Boy Named Sue” so you can take yourself to Wikipedia if you want an exhaustive list. And after his death, Shel received even further accolades and was inducted into the Nashville Songwriters Hall of Fame in 2002 and the Chicago Literary Hall of Fame in 2014. 

Besides contributing frequently to Playboy and maintaining a friendship with Hugh, Shel himself was a bit of a playboy. He never married, but he claims to have slept with hundreds — if not thousands!! — of women. Hubba hubba. Too bad for him though, he never slept with the two chicks behind Historic Shuffle. He did, however, have two kids with two different women: Shoshanna, who died in 1982 at the age of 11 from a cerebral aneurysm, and Matthew, who was born in 1984 and is still kickin’. Throughout his life, Shel often spent time on his houseboat, anchored in Sausalito, California, and he also owned non-houseboat homes in Greenwich Village, Martha’s Vineyard and Key West. 

On May 10, 1999, Shel passed away at age 68 after suffering a heart attack in Key West. The man of many stories had a long and storied career, rubbing elbows with all kinds of people of various ages from 2 to 92 and attending many a Playboy Party (trademark pending). So as you dip your apples in honey this year for Rosh Hashanah, remember Uncle Shelby and crack some possibly inappropriate jokes at the dinner table. He would definitely be proud as you usher in this forthcoming sweet, sweet new year. 

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