#111 - Shel Silverstein

Thank you for tuning in!  Welcome back!  After a summer hiatus due to my crazy schedule, we are back! 

On today's show, we will be talking about Shel Silverstein, the beloved author, songwriter, playwright, and frequent visitor to the Playboy Mansion (I'm not kidding!).  You will learn how Silverstein persevered through a tough childhood and became a revered children's author and musician.  We will also talk about his notable works and his legacy following his death in 1999.  

Toward the end of the episode, I mentioned Genevieve Wallace and how she is a very talented artist who created a brand new logo for me :)  You can check out her website here.  You can visit her Etsy store here.  And note - I was not asked to share any of these links, but she is just an awesome person and very talented so I want to tell everyone about her! If you visit my website or click here, you can check out the new logo on all kinds of merch!  Showcase your love for the podcast with some cool schwag!  From t-shirts to stickers to water bottles to duffle bags, my online store sells some cool stuff! 

I also shared information about an exciting new app called Q106.5 where you can listen to music from the '80s and '90s as well as several retro pop culture podcasts! Download the app on Apple & Android.  Pop Culture Retrospective is on there, you can listen to any episode, anytime!  Several other great podcasts are featured, too :) 

Transcript

If my memory serves me correctly, in an old home video from around 1988, my sister and I were sitting on our outdoor patio. My sister was sitting with her legs crossed, and when my dad panned the camera over to her, she lifted her foot toward the camera and said, “Shel Silverstein,” clearly recreating the iconic author photo from the book jacket  from “Where the Sidewalk Ends.” Recently, both of my kids have also become fans of Shel Silverstein's work, so between that and my sister's and my love for this beloved author, it seemed only fitting to dedicate an episode to him.It has been over 25 years since the passing of Shel Silverstein, yet his writings continue to impact generations of readers and will undoubtedly keep doing so. I was truly amazed by what I discovered about Silverstein, and I think you will be too. We will explore some of his most notable works, share some surprising behind-the-scenes information that I didn't expect (surprising is truly an understatement), and much more. While we won’t have enough time to cover everything that Silverstein did in his impressive career, I think you’ll learn why Silverstein continues to fascinate people and why children and adults alike, adore his writings, his artisity and his creativity.We can't cover all of Shel Silverstein's impressive career today, but I believe you'll discover why he continues to captivate audiences and why his writings, artistry, and creativity are adored by both children and adults. So, sit back, relax, and let’s nerd out on nostalgia.

Welcome back to the PCRP.  I am back after my summer hiatus and it feels amazing.  I am self employed and have two young children so the summers become overwhelmingly busy so I have to put a pause on the show most summers.  I swear I start going through withdrawal periods as I miss talking about pop culture, my sister, and collaborating with other retro lovers.  And I think now, more than ever, looking back at the past provides more comfort than I could have ever imagined.  So, let’s get on with the show! Sheldon Allen Silverstein was born on September 25, 1930 in Chicago, Illinois, to a Jewish Immigrant father named Nathan and his Chicago-born mother, Helen.  He spent his formative years in the Windy City.  His parents ran a bakery, which unfortunately was opened during the Great Depression, so money was always tight.  That being said, one positive of owning a bakery was that leftover baked goods often made their way to the Silverstein household at the end of the business day.  Neighbors who also struggled to get by would come to the Siverstein household looking for food.  Food was always rationed and wasting food was viewed as a sin.

As a child, Shel was very active.  He was always on the move and never required a lot of sleep, even later as an adult. Shel did manage to sit quietly and intently when radio shows came on, he especially loved the Grand Ole Oprey Show. 

He wanted to be an athlete with all of his heart.  He loved the Chicago White Sox and wanted to play professionally for them. Sadly, he didn't have much athletic talent so he decided instead to focus on art and writing, much to the dismay of his father.  His father detested his drawings so much that he often referred to them as “garbage.” Nathan Silverstein was allegedly a workaholic, so he didn’t understand why his son wouldn’t want to be involved in the family business or pursue something similar.

Further, according to writer Lisa Rogak, who we will touch on again in a moment, Shel’s father, Nathan, would say that he quote:  “didn’t puke his guts out in steerage to make it over here and then serve for a year in the war only to have his son throw his life away by drawing cartoons and daydreaming.” end quote. Shel disagreed with his father’s criticisms, so he worked tirelessly to hone his craft as an artist.  He began by tracing the drawings found in comic strips in the newspaper.  Later, Shel started writing stories to go alongside his drawings.  Since he wasn’t involved in many extracurricular activities, he was sort of a loner. Shel’s early years are described in detail from an excerpt from a book entitled- A boy named Shel : the life and times of Shel Silverstein by Lisa Rogak

Quote:  He also began to think up stories to go with the cartoons. “I didn’t have a lot of friends,” said Shel. “I just walked around a lot and made up stories in my head. Then I’d go home and write them down. That’s how I got started.” Shel also loved books. Because he was lonely, he turned to books for companionship. “One of the things that made me happy was to go to old bookstores and look through the books,” he said. “I would hold them, smell them, and even hug them. They were my friends.”  But he didn’t have the money to buy the books he wanted. So he vowed that when he got older and had money, he’d spend it on books. He dreamed of a day when he would have so many books on his shelves that he couldn’t read all of them in a year if that was the only thing he did.Drawing cartoons and reading books gave him something nothing else could: They gave him comfort.” end quote.

His mind was often focused on drawing, reading, or writing.  He loved books including those about Knights of the Round Table, the Civil War or anything about the conflict between Cowboys and Indians (now Native Americans). 

Drawing was truly an escape for Shel.  His home life was very chaotic, money was tight, and his parents fought a lot, often about how Shel was spending his time.  His father thought his artwork was a waste of time, and Shel’s mother wanted her son to follow his dreams.  

His parents relationship was so dysfunctional that Shel vowed to himself that he would never get married.  There were also people around him constantly between his sister, Peggy, and the neighbors downstairs.  Shel just wanted some quiet time to draw. Further, Shel’s parents were a bit on the older side for the time when he was born, so they didn’t have a lot of energy or patience to deal with his aspirations like younger parents would have, especially his dad.

Despite not being athletic, Silverstein did love sports.  As previously mentioned, his favorite team was the Chicago White Sox (I won't fault him for that as I am a life-long Cubs fan as was my sister, but I digress), and eventually he did work for the team by selling peanuts and hot dogs at the field.  

As a student, Silverstein was known as being defiant and argumentative.  School was not easy for Shel as he didn’t feel like he fit in.  He wasn’t a jock, he just liked to draw and read.  It has been said that Silverstein struggled with spelling. For example, he once misspelling his middle name on his social security card and often submitted manuscripts to his editors when he became a writer with significant spelling errors. Some researchers have said it’s possible he was dyslexic.  He was often bored while at school and would tell stories at inappropriate times.  Further, he was a small fish in a big sea.  He attended Theodore Roosevelt High School in Chicago, which at the time, housed over 4,000 students.  The school was so big that it took up 2 city blocks.  Surprisingly, Silverstein participated in ROTC while in high school.  The school is still in operation today, but there are a lot less students.  

After high school ended, Silverstein attended the University of Illinois, where he was allegedly expelled due to poor grades.  He then transferred to the Chicago Academy of Fine Arts. Although this school focused on one of his favorite subject areas, he felt like he didn't fit in at this art school.  He would often complete his assignments before anyone else, he would determine what he wanted the outcome to look like as he was doing a piece.  While his classmates would throw out page after page of their drawings, Silverstein would have it completed in one sitting and on one piece of paper.  His classmates would get frustrated with his process.  Presumably because he felt like he didn’t fit in, Silverstein then transferred to Roosevelt University where he studied Performing Arts and English. His first writing was published in the Roosevelt Torch, which was a student publication. Before he finished his degree, though, he was drafted into the military and served for several years from approximately 1949 -1955 during the Korean War. He created cartoons for adults while stationed in Japan and Korea.  Sometimes he would poke fun at military leaders in his comics, much to the dismay of the higher ups.  He reportedly got in trouble a few times for his antics.

When he returned home to Chicago, Silverstein continued to work harder and harder on his cartoon drawings and was soon published in notable periodicals such as Sports Illustrated and Look Magazine.  He is noted for saying that his previous attendance in college was ultimately a waste of time; he should have traveled the world instead so he could meet people.  

Silverstein started writing for Playboy!!! in the mid-1950s and continued to do so until the mid-1970s. He contributed dozens of pieces of his writing, and he was given the chance to travel around the world to create an illustrated travel journal called “Shel Silverstein visits….” I didn’t realize this, but Silverstein was also an accomplished musician and songwriter.  His first album, Hairy Jazz debuted in 1959.  The album included several original songs by Silverstein himself as well as several others devoted to his unique take on jazz music. His debut album, Hairy Jazz, was released in 1959. It featured several original songs by Silverstein, alongside others showcasing his distinctive approach to jazz music.

As a matter of fact, Silverstein has at least 800 songs registered with BMI which is not body mass index, but rather Broadcast Music Incorporated, which is a performance rights organization. 

Silverstein also wrote music for other groups, including several for Dr. Hook and the Medicine Show, Tompall Glaser, Loretta Lynn, and Johnny Cash.  Some of Cash's biggest hits were ones written by Silverstein, including “25 Minutes to Go,” which was about a man on death row, and “A Boy Named Sue,” which was released in the late 1960s. Here are a few lines from A Boy Named Sue and if you listen closely, you can tell this is clearly the writing of Shel Silverstein:

Well, my daddy left home when I was three

Didn't leave very much to my mom and me

Except this old guitar and an empty bottle of booze

Now I don't blame him 'cause he run and hid

But the meanest thing that my daddy ever did

Was before he left, he went and named me Sue

Well, he must've thought that it was quite a joke

And I got a lot of laughs from a lots of folk

Seems I had to fight my whole life through

Some gal would giggle and I'd turn red

And some guy'd laugh and I'd bust his head

I tell you, life ain't easy for a boy named Sue

But I grew up quick and I grew up mean

My fist got hard and my wits got keener

Roam from town to town to hide my shame

But I made me a vow to the moon and stars

I'd search the honky tonks and bars

And kill that man that gave me that awful name

Well, it was Gatlinburg in mid-July

And I just hit town and my throat was dry

Thought I'd stop and have myself a brew

At an old saloon on a street of mud

There at a table, dealing stud

Sat the dirty, mangy dog that named me Sue

Silverstein wrote music for most of his professional life, with one of his last musical works being with a group called “Old Dogs,” who released an album of the same name in 1998.  The group felt there were no good songs about getting old, so the foursome, which included Silverstein as a member and lead song writer, did just that.

And, as if being an artist, an author, and a songwriter wasn’t enough, Silverstein was also a playwright, wrote “The Devil and Billy Markham” and the 1981 hit “The Lady or the Tiger.” 

Since Silverstein is most known for his writings for children, let’s back up a little bit and discuss his journey as an author for younger audiences. Even though much of his earlier drawings and writings were for adults, Shel had a few people in his circle who believed he could also be a successful children’s author.   The individual who was likely the biggest influence on his author journey was a friend named Tomi Ungerer, who was an author and illustrator of children’s books.  Ungerer brought Silverstein to meet a well-respected editor at Harper and Row named Ursula Nordstrom.  

She too could see Silversteins talent and would allow him a lot of autonomy which is exactly what Shel wanted. Had Shel been forced to drastically edit his work, who knows what would have happened. Silverstein would go on to publish several books which included his special way of writing and his unique drawings.  Nordstrom once said of Silverstein:  “he published good books for bad children.” 

This supportive relationship led to his first publication for children entitled “Uncle Shelby’s Story of Lafcadio: The Lion Who Shot Back” in 1963.  The character of Lafcadio first appeared in a story Silverstein wrote for Playboy but the lion’s story evolved into a children’s book.  Silversteins official website describes it this way:  “Shel Silverstein's first children's book, Lafcadio, the Lion Who Shot Back is a whimsical tale of self-discovery and marshmallows.Is a famous, successful, and admired lion a happy lion? Or is he a lion at all? Written and drawn with wit and gusto, Shel Silverstein's modern fable speaks not only to children but to us all!”

Giraffe and a Half was published in 1963 and has been described as:  “If you had a giraffe and he stretched another half, you would have a giraffe and a half. But what happens if you glue a rose to the tip of his nose? Or if you used a chair to comb his hair? Join this giraffe on a rollicking and ridiculous journey that will charm readers from beginning to end.”

His next book, The Giving Tree which was published in 1964, made Silverstein a household name and set him down the path of success as a children’s author and illustrator.  Again, the official website provides an excellent description:  “So begins a story of unforgettable perception, beautifully written and illustrated by the gifted and versatile Shel Silverstein. This moving parable for all ages offers a touching interpretation of the gift of giving and a serene acceptance of another's capacity to love in return. Every day the boy would come to the tree to eat her apples, swing from her branches, or slide down her trunk...and the tree was happy. But as the boy grew older he began to want more from the tree, and the tree gave and gave and gave. This is a tender story, touched with sadness, aglow with consolation.”

“The Giving Tree” took a total of 4 years to get published.  There was a lot of back and forth when it was being written - some said it was too sad, and some said it was too short.  Despite the criticism, the Giving Tree has been a beloved book to millions of people across the globe since it’s release.

Who wants a Rhinoceros was also released in 1964 and asks readers about who they may want to have as a pet.

Need a pet? What’s the best kind to get?

A dog, a cat, a frog, a rat?

How about a cheap rhinoceros?

He’s funny and sweet and loyal as they come.

He’s huggable and lovable.

So who wants a cheap rhinoceros?

Maybe you!

While Silverstein was publishing children’s books left and right, he was still writing for adults in Playboy. His drawings appeared in every issue of the magazine while working with the company.  During his time writing for the infamous publication, he became close friends with Hugh Hefner. Apparently, he enjoyed the company of 100s if not 1000s of women.  He also met a woman named Susan Hastings at the mansion, eventually they had a daughter together named Shoshanna Jordan Hastings in 1970.  Tragically, Susan passed away when their little girl was just 4 years old. She would go on to live with her maternal Aunt and Uncle, who would raise her much to the gratitude of Silverstein.  And tragedy would strike again seven years later when little Shoshanna died of a brain aneurysm when she was just 11 years old.  Silverstein appreciated his close friends who recognized his painful loss, not just when it happened, but in the days, weeks and years that followed. Several years later, when “A Light in the Attic” was published, Silverstein would dedicate the book to her.  More on that later.  And although he didn't write for Playboy his entire life, he did maintain a space at the mansion for him to rest his head and sleep, if you will, over the years.  He would visit the mansion several times a year, for many a rendezvous with the opposite sex. 

In 1974, we got to start enjoying Where the Sidewalk Ends.  We had this book as children and I can remember reading it over and over again.  

My very favorite poem was entitled “For Sale.”  The poem talks about selling your sibling which I found hilarious as a kid both because sometimes my sister drove me crazy and I know I drove her crazy, too!   

One sister for sale!

One sister for sale!

One crying and spying young sister for sale!

I’m really not kidding,

So who’ll start the bidding?

Do I hear the dollar?

A nickel?

A penny?

Oh, isn’t there, isn’t there, isn’t there any

One kid that will buy this old sister for sale,

This crying and spying young sister for sale?

Other poems from this collection include:  “Jimmy Jet and his TV set,” "Sarah Cynthia Sylvia Stout Would Not Take the Garbage Out,” and “Captain Hook.” 

Where the Sidewalk Ends was dedicated to several people including Ursula Nordstrom who really believed in Silverstein.  An audio edition of the book was released in 1983 and it won a grammy for best recording for children.  The entire album was performed by Shel Silverstein himself!

The Missing Piece was published in 1976.  This book is not a collection of poems like his other books, but rather a fable.  As described on Shel Silverstein.com, the book is:  “It was missing a piece. And it was not happy. What it finds on its search for the missing piece is simply and touchingly told. This inventive and heartwarming book can be read on many levels, and Silverstein’s iconic drawings and humor are sure to delight fans of all ages.”

A Light in the Attic was published in 1981 and as previously mentioned, this book was dedicated to his daughter Shanna.  On one of the first few pages there is a drawing of a potted plant with a sign reading- “To Shanna.”  This book as well as Where the Sidewalk Ends, I think, are two of the books that make children fall in love with the writings of Silverstein, including my youngest son.  He was recently on a Shel Silverstein kick and I found myself laughing so hard I cried over this poem entitled- “Little Abigail and the Beautiful Pony.”  

Because my family loves this poem so much I invited my 9 year old son Kai, to read it.  Enjoy his fun interpretation of this beloved yet dark, poem.

Some other poems from this book include: “How Not to Have to Dry the Dishes,” “The Sitter,” and “Adventures of a Frisbee.” A Light in the Attic was the first children’s book to break into the adult NYT best seller list, where it remained for over 3 years. 

The publication of Falling Up in 1996 would be Silverstein's last before he passed away.  Some of the poems in this book included:  “Big Eating Contest,” “Foot Repair,” and “Eggs Rated.” This book was dedicated to his son, Matthew via a drawing of a person wearing a hat with the words:  “To Matt” written on top.  Since I found the title of Eggs Rated to be quite an intriguing, I figured this woud be a good one to share.

Throughout his life, Silverstein was the antithesis of what it meant to be a stereotypical celebrity.  He did everything he could to avoid being discovered while out in public.  As a result of this, he avoided places like the grocery store.  Instead, he would order room service whenever he was at the Playboy Mansion, and would juice fruits and vegetables when staying at one of his residences.  Apparently, he did not like being approached for autographs, or being spotted while out in public.  Also, he was not an avid technology user, he preferred to do all of his writing on yellow legal pads.  

He preferred landlines to cell phones.  Furthermore, he avoided banks as much as possible, too.  Instead, he would rely on friends to cash his checks, giving him enough funds to take care of his needs for several weeks at a time.  In addition, Silverstein was often viewed as a bit of a nomad.  He never stayed in any one spot for very long.  A friend described his housing situation as Silverstein living in perpetual spring.  He would live in a houseboat in Sausalito, CA, then transition to NYC for a few months, followed by Martha’s Vineyard, Key West, FLA and even as far as Thailand sometimes. Apparently, Silverstein really loved living in Thailand because he could pretty much go anywhere without being recognized.  During one of his stints in Key West, FLA, he met a woman named Sarah Spencer.  She worked in the tourism industry, and together, they welcomed a boy named Matthew in 1984. Matthew, now a grown adult, apparently works in the music industry, following a bit in his father's footsteps.  

He enjoyed a good Cuban cigar at times and the company of close friends. 

He often used the pen name Uncle Shelby as he didn't want to be viewed as some sort of “stuffy dad,” but rather a fun uncle.  

In the interest of time, we cannot discuss all of Shel Silverstein’s books for children, but some of his other notable works in this genre include:  Everything On It, Different Dances, Don’t Bump the Glump, Runny Babbit, and the Missing Piece Meets the Big O.  “Runny Babbit” was the first posthumous publication, released in March of 2005.

I think Shel Silverstein’s perspective on the world around him could best be described in his poem Falling Up from the book of the same name.

I hope you have enjoyed this look back on the fascinating life and career of the one and only Shel Silverstein.  I had no idea when I was reading “Where the Sidewalk Ends” 30+ years ago (and even more recently with my own kids) that the author was as unique of a character as the drawings in his books.    

Shel Silverstein died on May 10, 1999 in Key West, Florida of a heart attack.  He is burried at the Westlawn Cemetary in Norridge, Illinois, which is on the outskirts of Chicago.  His books have been published in almost 50 different languages and have sold over 20 million copies.  Silverstein’s works have already been enjoyed by 3 generations of readers and there are no signs of that momentum coming to a halt.  

Make sure you visit popcultureretrospective.com to connect with me!  Here you can find links to blog posts, guest profiles, leave a review or even shop for PCR Podcast merchandise.  And in case you didn’t know, hitting the 5 year mark has also meant updating a few things including the official, brand-spanking new Pop Culture Retrospective logo created by an incredibly talented artist and designer, Genevieve Wallace.  I will put a link to her website in the show notes.  If you go to the PCR website and click on merchandise, you can see dozens and dozens of items which are rocking the new logo and it all looks amazing, I am biased, but seriously it does!

Genevieve also has an Etsy shop which is where I first saw her incredible and often retro-inpired work.  I hope you will join me for my next show where we will discuss another fascinating facet of the 80s, 90s and early 2000s in memory of my sister, Rebecca.