Chapter 1

When he was five years old, Shel Silverstein taught himself to draw by tracing over the comic strips in the newspaper. His favorite was Li’l Abner by Al Capp.

He placed a sheet of paper over the strip and traced over the faces, the hands, the buildings, the scenery, everything. “The first thing I did was copy Al Capp,” he said. “He really influenced me. It was the most wondrous thing for me. Al Capp knew how to draw people, shapes, bodies, hands. He knew how to draw well, so I learned how to draw well.”

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.

“He was a lonely kid,” said songwriter Drew Reid, an old friend. “He was always aware that he was different from the other kids around him. Let’s face it, musicians, artists—anybody who’s creative—we’re all kind of wacky because we don’t look at stuff the way other people do. And Shel always knew that.”

On March 3, 1891, twenty-nine-year-old Sigmund Balkany, a laborer from Bohemia, arrived at the port of New York aboard the Aller passenger ship along with thousands of other European immigrants who wanted a better life in America. He spent a few years in New York before moving to Chicago.

Rae Goldberg was born in Hungary in March of 1876 and immigrated to the United States at the age of twelve. She met Sigmund Balkany in Chicago, and they married in 1897 or 1898. Helen, their first child, was born on January 5,1899.

In 1900, Sigmund found work at a tannery, and the family of three rented a house at 911 Milwaukee Avenue near Wicker Park, in a section of Chicago known as West Town. Eastern European Jewish immigrants flocked to the neighborhood, known as a community rich with political radicalism. However, the Milwaukee Avenue corridor also had its share of gangs and violence, which author Nelson Algren described in his 1949 book, The Man with the Golden Arm, the story of a heroin addict released from jail who returns to his old neighborhood and fights to keep from succumbing to the drug again. “Louie was the one junkie in ten thousand who’d kicked it and kicked it for keeps,” wrote Algren. “He’d taken the sweat cure in a little Milwaukee Avenue hotel room, cutting himself down, as he put it, ‘from monkey to zero.’”

By 1910, the growing Balkany family had moved less than a mile west to 2235 West Potomac Avenue, still in West Town but closer to Humboldt Park and in a more residential area. It was a definite step up for the family, since the neighborhood had newer and more spacious housing stock and apartments.

Sigmund had left the tannery and opened a small grocery store, where Rae worked alongside him. Their family had expanded with two more daughters: five-year-old Esther, and Martha, who was three.

In 1916, seventeen-year-old Helen began clerking for her father at his grocery store located at 2659 Evergreen Avenue, a relatively new building built in 1912 about a mile from their Potomac Avenue home. That move didn’t last long, for Sigmund consolidated his family and grocery store and moved them both to 1458 North Washtenaw Avenue the following year, a few blocks away from the previous store. The two-story building was built in 1914 and had five apartments on the second floor and the store at street level. By 1923, Helen was in charge of running the grocery store, and she enjoyed the autonomy it gave her. At the age of twenty-four, an old maid by the standards of the day, she was in no hurry to get married.

On December 23,1924, everything changed when her father, Sigmund Balkany, died.

Nathan Silverstein was born on July 1, 1890, in either Russia or Poland, the second of five children born to Abraham and Fannie Silverstein. Harry was born a year earlier, and Julius and Jack were born in 1899; a sister, Frieda, followed in 1902.

The Silverstein family’s journey to America took the form of a chain migration, where one child at a time traveled to the United States—typically, the sons went first—and once he earned enough funds to send back to the old country, another could afford to come over. Harry arrived in the United States in 1906, and Jack immigrated in 1911. Julius followed in 1913, and Nathan was the last son to immigrate, in 1915. The family initially settled in the Bronx before heading west to Chicago.

It was common for brand-new immigrants to enter the military as World War I was raging. Both Julius and Nathan signed up for the military in 1917 and were discharged in April 1918. However, the war interrupted the migration of the family, and Fannie and Frieda didn’t arrive in the United States until 1920.

By 1923, Jack and Nathan had started a bakery known as Silverstein Brothers and lived with their older brother Harry at 2601 Walton Street. Now established in their own business, they set out to find wives.

Nathan found his future wife living about a mile away.

There was little time to lose. When Nathan’s engagement to Helen Balkany was announced in the Chicago Tribune on June 6, 1926, he was thirty-six and Helen was twenty-seven; the couple was unusually advanced in years during an era where getting married at the age of nineteen meant you were over the hill. They were wed five months later on Halloween 1926, by Rabbi Julien Gusfield at the Hotel Windermere East in Hyde Park. The choice of wedding venue was unusual for a couple from the northwest side of Chicago. The Windermere, hotel residence of Pulitzer Prize–winning author Edna Ferber among others, was a pretty swanky location for a 1926 wedding.

They may have picked it because the brothers had grand ambitions for their business amidst the heady glamour and free-flowing money of the 1920s. They changed the name of their bakery from Silverstein Brothers to the Service Cake Company and began to plan for the construction of a 105,000-square-foot, one-story brick building at 834–38 North Western Avenue, which would be completed in 1930.

After they were wed, the new Mr. and Mrs. Nathan Silverstein moved in with Helen’s mother, her sisters, and a new brother-in-law at 1458 North Washtenaw. The widowed Rae Balkany was no longer running the grocery store, and instead, husband and wife Isadore and Eva Hershberg operated the store and lived with their family in one of the apartments on the second floor.

Sheldon Allan Silverstein, Nathan and Helen’s first child, was born on September 25, 1930. From the time he was an infant, Shel was surrounded by people and nonstop noise, from the families living in the other apartments to the chaos on the street below outside the store to people constantly clomping up and down the stairs and knocking on the Silversteins’ door to see if the young family needed anything.

Helen was thirty-one years old and Nathan had just turned forty when Shel was born, and his parents’ mature years—especially his father’s—profoundly influenced Shel’s childhood. The boy had to walk on eggshells around the house and tamp down the typical manic energy of a naturally curious young child whenever his father was home. He had a surplus of energy, and even as a kid he didn’t need much sleep, which would be true all his life.

The Silverstein brothers had the misfortune to open their new bakery during the first full year of the Great Depression, and the financial stress made Nathan tense and short-tempered during the few hours he spent at home each day.

With money so tight at the onset of the Depression, most days the Silverstein family ate whatever Nathan could bring home from the bakery, supplemented by Helen and Rae’s creativity. (Since they were no longer running the grocery store downstairs, they couldn’t scrounge off the shelves when things got tight anymore.) Wasting food was just about the biggest sin in the world. Nathan provided his family with day-old bread and pastries from the bakery, but of course, being a kid, Shel wanted what he couldn’t have: the rare treats.

Shel’s favorite food growing up was any creamy type of dessert, especially pudding and the custard known as junket. He was raised in a household filled with other people, where neighbors showed up unannounced for dinner because they had no food, and portion control was the rule.

“I never had enough junket,” he said. “When I was a kid, my mother used to make junket and put it into little glass dishes and put them in the refrigerator, and maybe there were six little glasses and I would get to eat one or two of them, but that was never really enough, and in my whole life I have never really had enough junket.”

Shel also wanted something more than the wax lips and bubble gum that were all most kids could afford to buy during the Depression at a penny apiece.

“When I was a kid and I had a box of that lousy stinking wax candy, I really wished I had enough money for a Hershey bar or a Mars bar instead,” he said. “That would really knock me out because I wanted that nickel candy, not the penny candy and baseball cards with bubble gum.”

Privacy and quiet grew even more scarce after Shel’s sister, Peggy, was born in 1934. It couldn’t have been easy for Nathan, having another mouth to feed during the depths of the Depression. But his son began to retreat more in order to forget about the tension and strife that surrounded him. He buried himself in books, especially fantasy books, comic books, and Little Big Books that he borrowed from the library. Arthur Rackham, a Victorian British fantasy children’s book illustrator whose paintings appear in the book The Romance of King Arthur and His Knights of the Round Table, was a particular favorite, and Shel also loved stories about cowboys and Indians and others that were set during the Civil War.

Young Shel also listened to the radio, particularly the country-and-western stations. His favorite artist was Ernest Tubb, a pioneer of country music who was a regular on the Grand Ole Opry radio show in the 1940s. Tubb’s first big hit, “Walkin’ the Floor over You,” came out in 1941.

“Shel once told me that when he bought his first Ernest Tubb record, he wore it out playing it over and over again,” said songwriter Fred Koller.

Shel became a student at Charles R. Darwin Elementary School in 1935 around the same time Nathan decided it was time to move his family out of his mother-in-law’s house and into a place of their own. Unlike many businesses that had been driven into bankruptcy by the Depression, the Service Cake Company survived the worst of it, so Nathan moved his family to an apartment building at 2853 West Palmer Street.

Once Shel entered school, in addition to drawing constantly at home, he was bored with the subjects and started doodling in class. As much as he could, anyway, without getting rapped on the knuckles with a ruler or worse.

Drawing became his escape: It helped block out the constant noise from the tenants, but most important, he discovered that it also stopped the voice in his head. That voice was his father’s, who totally disapproved of Shel’s artistic efforts. Nathan would regularly berate Shel, calling his drawings and cartoons garbage. Nathan would say that he 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.

His father and mother were constantly arguing, and most of the time it was about Shel. Drawing also helped Shel to ignore his parents’ fighting.

“His mother and father warred continually,” said Judy Henske, a folksinger who met Shel in the late 1950s. “His mother told him he could do anything he wanted while his father expected him to join the family business.”

As long as he was drawing cartoons, reading books, or listening to the radio, Shel was able to keep the doubts and insecurity at bay. The moment he stopped, everything came rushing back, the negativity and noise, louder than before.

It was all a matter of control. While he couldn’t control the world that existed away from his pencils and sketchpads—including World War II, which began to ratchet up the angst in his household even more—he could control the world in his imagination. And so he began to retreat to that world more often, away from the noise and constant conflict.

Once he had mastered copying Al Capp cartoons, studying them from every angle, Shel began to study the work of Virgil Partch, who went by the name of VIP, an avant-garde cartoonist popular from the 1940s through the 1960s. Partch’s work resembles Hanna-Barbera characters like the Jetsons and the Flintstones, except he was drawing in that style at least two decades earlier. Partch drew for Walt Disney Studios for four years during the Depression, where his style was most clearly shown in the Donald Duck cartoon Duck Pimples. He came to disdain the three-fingered style common to Mickey Mouse and other symbols of the Disney empire. “I draw a stock hand when it is doing something, such as pointing, but when the hand is hanging by some guy’s side, those old fingers go in by the dozens,” he once said. Shel would later follow VIP’s example in always striving to draw a five-fingered hand.

Shel was in good company in studying the top cartoonists of the day, because the vast majority of them were Jewish: VIP, Stan Lee, and Shel’s hero, Al Capp. Plus, Max Gaines had founded DC Comics, and such top comic superheroes as Superman, Batman and Robin, and Captain Marvel were created and drawn by Jewish cartoonists. Although Shel knew he only wanted to be a cartoonist and not pursue any of the other graphic arts disciplines, other Jews at the time didn’t have a chance to break into the generally gentile fields of advertising or the fine arts, and newspaper comic strips were all but closed to them. But because comic books were a brand-new field—and most of the publishers were Jewish—they were the only viable avenue into the field for a kid who wanted to draw—and who happened to be Jewish.

In addition to cartooning, Shel also loved baseball, specifically the Chicago White Sox. Like millions of other boys his age, Shel dreamed of playing third base for his beloved team, but he was an unathletic, gawky kid. The closest he would get to his dream was as a vendor at the baseball games, where he roamed the aisles of the bleachers to hawk peanuts and hot dogs to fans.

Later on, he would consider his lack of physical agility a blessing in disguise. “If I had my choice, I would have been a great third baseman with three girls on my arm,” said Shel. “By the time I could get the girls, I already knew how to write poems and draw pictures. Thank God I was able to develop these things, which I could keep, before I got the goodies that were my first choice.”

Shel was not a particularly good student. His classes bored him and his mind wandered as a result, making up stories in the middle of class that were vastly more entertaining than what was going on in the lesson. He also was a poor speller; today, he might be diagnosed as dyslexic, but the truth was that Shel’s mind was operating at such a pace that he couldn’t write quickly enough to get everything down on paper. In fact, in later years, editors and art directors at Playboy and his book publishers would bitterly complain about Shel’s surplus of misspelled words. When he applied for a Social Security card at the age of fifteen, he actually misspelled his middle name, crossing it out before writing it down correctly.

When World War II broke out in 1939, the curriculum at public schools across the country was retooled toward the war. Teaching basic military skills was the rule when Shel entered Theodore Roosevelt High School in September of 1944. The high school was one of the largest in the nation, covering two city blocks, and was one of the best equipped as well. Its capacity was just over four thousand students and contained ninety classrooms and a variety of sewing rooms, music rooms, auto shops, three woodworking shops, science laboratories, gymnasiums, swimming pools, auditoriums, and a cafeteria that could seat one thousand.

One of the programs at Roosevelt was the Reserve Officers’ Training Corps (ROTC). Shel signed up for that program when he turned fourteen. During his tenure, he received several honors, including an Officer Eagle Medal and a medal of General Excellence. Despite his ROTC accomplishments, others at Roosevelt High remembered Shel as a combative and uncooperative student.

Art Paul, Playboy’s first art director, said he later heard some gossip about Shel’s high school days. “Apparently, a lot of people thought he would never succeed in life, because he didn’t get along too well with the other students,” said Paul. “They said he was such a character and had such an unusual outlook on life that they were surprised that the Shel Silverstein whose work was all over Playboy was the same Shel Silverstein they went to school with. I could see where he’d have trouble because his mind was very active, and creatively so. And he said things like he felt them. I think that he had a problem being normal.”

Indeed, Shel hated conformity. “When I was a young kid, about once a year we had to buy some new clothes and I’d pick out a new coat or suit,” he said. “Someone would always ask if I was sure this is what they’re wearing this year. Well, who is this ‘they’ and what difference does it make what they’re wearing? I’ll wear what I want to wear!”

Of course, conformity was what his father wanted, to be safe. After a life filled with strife and uncertainty and the difficulty of adjusting to a new country, all Nathan wanted was to work hard and come home to a hot meal and a roof over his head at the end of the day. Shel wanted the opposite. He wanted excitement and adventure, and early on he made a promise to himself that he would never get married, if his parents’ stormy relationship was what marriage meant. He kept that childhood vow, remaining single for his entire life.

Above all, Shel wanted nothing more than to draw, to earn his living from it, not to work sixteen hours a day in a hot bakery ordering other people around in a job he hated. A big reason for the discord between Nathan and Helen was because she supported her son in whatever he wanted to do while her husband thought Shel should work in the family business, on weekends at first and then later full-time.

Once the war ended, Shel’s father turned up the heat. “I’m grateful I have a job,” Nathan would berate Shel. “I’m grateful I’m even alive. If I didn’t get out, you wouldn’t even be here, and yet all you do is daydream all day and scribble cartoons that don’t make sense.” Nathan held out high hopes that Shel would join the family business after graduating from high school or college. Even though Nathan belonged to a generation that wanted their children to do better than themselves— “Why do you think I came over? It wasn’t for me, it was for my kids” was a common defense—he also came from the old country, where sons didn’t dare question the issue of joining the family business. Shel, of course, did nothing but question those expectations.

Nathan was only looking for the business to continue. After all, he was fifty-eight years old when Shel graduated from high school, and it was important that his son take his place in the family business.

Chris Gantry, a Nashville musician and songwriter who would later collaborate with Shel on a number of songs, grew up in a family similar to Shel’s. “My father was the same way,” he said. “He wanted all his kids to be involved in the family business. He worked sixteen hours a day at his business, and to do anything else was alien to him. I can’t tell you how many times I heard him say, when I was a kid, ‘Goddammit, what do you care about banjos and ukeleles?’” Shel’s father didn’t think that writing songs and drawing cartoons were legitimate things to do in life.

Shel graduated from Roosevelt High School in June 1948, and he went on to college in the fall. In interviews, Shel said that he attended the University of Illinois at Navy Pier—now known as the University of Illinois at Chicago—and that he was kicked out. While no records show that he was a student at Navy Pier campus, they do indicate that he attended the University of Illinois at Urbana-Champaign from September 1948 through June 1949, successfully completing his freshman year.

Why did he fib about the college he attended, even though both schools are part of the same university system? The Urbana-Champaign school was and still is considered the more prestigious of the two, while the Navy Pier campus was strictly a commuter school for working-class students and for veterans attending on the GI Bill.

Nathan may have insisted that he attend the Urbana-Champaign campus since it was a definite step up classwise from Navy Pier. It could also have been due to a Jewish quota at the university. Most state universities during this period had restrictive policies about Jewish admissions; the quota at the Navy Pier campus might have been filled while the Urbana-Champaign campus had some openings.

The year he spent at Urbana-Champaign was undoubtedly Shel’s first exposure to a gentile hierarchy based on money, father’s occupation, and family connections, and he must have been profoundly uncomfortable there, a real fish out of water among the privileged class. Also, Urbana-Champaign was a very fraternity-oriented campus and Jews were excluded from mainstream fraternities.

It was very early on, then, that Shel began to create a mythology and false history in rejecting the intellectual and “snobby” Urbana-Champaign and creating a false association with the student body at Navy Pier. He never wished to be mistaken for the kind of Jew who wanted to be upwardly mobile, which meant shoehorning himself into the gentile world.

“The first semester they put me on probation,” he said. “The second semester they threw me out.” This statement only augments the mythology of Shel as a combative student and a free spirit. After finishing his freshman year, he enrolled in the Chicago Academy of Fine Arts, known today as the Art Institute of Chicago, one of a handful of schools in the United States that taught cartooning.

But even there, he didn’t fit in. He worked differently from other students, whether he was writing or drawing. While other students would first scratch out a few ideas, scribbling, drafting, crossing out, erasing, and finally crumpling the paper in frustration and tossing it into the wastebasket, Shel’s ideas always came out fully developed. He’d turn the idea over in his mind before committing it to paper. And then, when it finally came out, it was done. He knew so in his heart.

But his teachers didn’t agree. They were there to provide guidance, and Shel steadfastly refused their help. After a year, he left.

His next stop was Roosevelt University. He’d stay for almost three years at Roosevelt, which he credited to Robert Cosbey, an English teacher who saw the talent beneath Shel’s defiance and began to work with him to develop it. As a result, Shel began to blossom.

“Bob Cosbey was the most important influence on my writing, and on many other people’s writing,” said Shel. “He was the only good thing I got out of Roosevelt University.”

“We went to Roosevelt because we could afford it,” said Jay Lynch, a cartoonist who would later work with Shel at Playboy. At the time, Roosevelt—which was founded by Eleanor Roosevelt—cost only six hundred dollars a year, and it was right in the city, which was convenient for Shel, who was still living at home. “It was a very socialist school, where most of the students were minorities living in the inner city. But nobody ever graduated from Roosevelt,” said Lynch.

Shel worked at the school newspaper, The Roosevelt Torch. He helped to lay out the paper and wrote a number of one-panel cartoons that generally poked fun at campus life. One cartoon showed a couple of men walking out of a classroom, and one of them is dressed in a bathrobe, pajamas, and slippers. The caption: “I always fall asleep during that guy’s lectures.” Another cartoon is set in a lecture hall, a professor standing at the podium with his arm around Groucho Marx. “And here, to speak on the philosophy of Marx, we have . . . ,” reads the caption.

Shel also wrote a column called “The Garbage Can.” In the February 16, 1951, issue, he wrote a piece called “Recipe for Beating the Draft,” in which he instructed readers to gather a sharpened pencil, a garbage pail, and one “stout heart.” Then he got down to business:

“Insert the pencil into your ear and push until you hear your eardrum go ‘Pop!!’”

In the same column, he wrote, “Attention Freshmen! What are you doing here? The tuition at Wright [College] is only ten dollars a semester.”

The staff was supposed to get paid, but the newspaper typically lacked the money to spring for much beyond the printing bills. Instead, Shel and other staffers were compensated in typewriters.

Despite Cosbey’s influence and encouragement, Shel didn’t graduate from Roosevelt, because Uncle Sam came calling. But even if he hadn’t gotten drafted into the army, he would have left anyway. “My grades weren’t that good, but I’d had too much college anyway,” he said. “I should have been out working and living life. Imagine: four years you could have spent traveling around Europe meeting people, reading all you wanted to anyway, and instead I wasted it at Roosevelt. I didn’t get laid much and I didn’t learn much. Those are the two worst things that can happen to a guy.”

Copyright © 2007 by Lisa Rogak. All rights reserved.