Shel Silverstein is known as a children’s author, but his life and career cannot be contained within the stereotypical parameters of one artform.

No one would call Shel Silverstein a failure. But in many ways, he turned away from the things we associate with success. He never settled down or got married. Though he sold millions of children’s books, he didn’t really like children. In his youth, he couch-surfed among friends, and later in life, bounced between homes of his own.
It’s been seventeen years since Shel, a Chicago native, died suddenly of a heart attack at age sixty-nine. He was an outspoken man who stayed out of the societal limelight. He talked rapidly and with a signature rasp. Most remember Shel for his children’s novel, “The Giving Tree” (1964), and his squiggly lined children’s poetry collections, “Where The Sidewalk Ends” (1974) and “A Light in the Attic” (1981). What the devoutest fans know is that he completed it all while a cartoonist for Playboy magazine and later found a niche in songwriting and the theatre. Shel wanted to try everything, and each medium in which he dabbled brought to light a different side of who he was.

Shel believed art carved out the identity of its artist. “Art is an extension of the man,” he told Studs Terkel in 1961; he swore off interviews in 1975. “Anything a man does will reflect his thinking and will be his ideas.” If we take Shel at his word, then the artist’s vast body of work tells an intricate story of a conflicted man.

If we take Shel at his word, then the artist’s vast body of work tells an intricate story of a conflicted man.

Time magazine eulogized Shel, describing him as “a recluse totally engaged in life.” In candid photos of Shel, we see glimpses of that dichotomy brought to cognizance. In some, he’s flashing a gap-toothed smile as if barely holding back the flood of his next punchline. In others, he somberly slouches against a wall or a chair, cradling a guitar against a loose-fitting, unbuttoned shirt.
As a children’s author, Shel’s voice was optimistic and full of wonder. By contrast, his personal songwriting is anchored in profanity and harsh judgments of others. Some of his cartoons are downright offensive; though, the songs he wrote for others offer wisdom hugged by a country twang. His works and personas don’t come in eras but ebb and flow throughout the time-line of his life. In 1975, he told Terkel, a fellow Chicagoan, “I don’t have any idea that I wanna put across. My ideas change and I’ve got a lot of different ideas that maybe knock heads with each other.”
Shel was complicated. His magnetic personality drew hundreds of women and high-profile creative friends to his side. Others were afraid to approach him. Later in life, strangers perceived him as homeless. Friends remember Shel, or, affectionately, “Shelly,” as a man who showed up at your doorstep, without warning, ready to talk, always with an idea, a joke, or a story. He had a stance and an answer for every inquiry. He believed in life perfected down to the simplest detail, like all of his books should be printed on a certain quality of paper and that none of them should ever be published in paperback. He was free-spirited but with a narrow view of what was best for those who live freely. Like his writing, he always had a cock-eyed, unexpected twist to the way he spoke.

To appreciate, not necessarily understand, we start at the beginning. In 1930, Shel was born, and Shel was born a Chicagoan.

Once there was a little boy … and he loved to draw. Shel started drawing at five years old, tracing newspaper comic strips in his maternal grandmother’s house in Humboldt Park Chicago (1458 N. Washtenaw Ave.), where he lived with his parents, Nathan and Helen. The environment of the home was tense. Not only was it packed with relatives, but Shel’s father’s bakery, first called Silverstein’s Bakery then renamed Service Cake Company (834-48 N. Western Ave.), opened in 1929—the first year of The Great Depression. Despite the odds, the bakery survived, and after Shel’s only sibling, Peggy, was born in 1934, the Silversteins moved into their own home, a second-floor apartment at 2853 Palmer Street in Palmer Square. Shel attended Darwin Elementary in Logan Square and then graduated from Theodore Roosevelt High School in Albany Park in 1948. Roosevelt High School is where he’d land his first cartooning role, sketching for the high school newspaper. Fellow classmate Lionel Kramer, who now lives in Northbrook, was the one to assign it. “We had a basketball coach who wasn’t very popular, and we had an inside joke that was a secret thing among us, that this coach’s nickname was Pig,” Kramer said. “Shel was very creative so he wrote a little verse ‘Ode to a Pig’ and I was able to slip it past the newspaper supervisor and publish it.”

Kramer described Shel as a “nice guy” and also a “loner,” continuing, “He never really socialized and pretty much just stayed to himself. We could tell he marched to the beat of his own drum.”
Shel had friends in school but didn’t do much after school hours, partly because of his after-school job selling peanuts at the original Comiskey Park. Kramer said he offered to sneak them a free bag if they were ever catching a game. “We were always friendly, but he wasn’t easy to be close to,” Kramer said. “I never met anybody like Shel.”

Kramer never saw Shel after graduation; though, he did reach out to him a couple of times, he said. “We lost track,” Kramer said. “I’d hear about him, and of course he was our famous graduate. We saw him on Johnny Carson. But he never came to any class reunions.”

Arnie Kamen, a 1950 graduate of Roosevelt, still has some of Shel’s cartoon clippings and reached out to Shel to attend those class reunions. “I knew Shelly from the word ‘Go,’ ” Kamen said. “He was a flat-out funny guy.”

Kamen also described Shel as someone who stuck to himself, that is until someone asked him to speak up. “It depended on who he was talking to,” Kamen said. “He was a little bit different and outward in certain ways.”

Susan Licciardi, librarian at Roosevelt, said that the school doesn’t have any events or curriculum to honor Shel but that they do have a plaque outside the library honoring his contribution to literature. Shel’s only photo in his graduating yearbook is his class photo, despite being a part of numerous clubs, the orchestra, and performing in the school play. “It’s really too bad,” Licciardi said. “But the kids know that he went here.”

Shel, even as a teenager, stayed out of the limelight. After high school, Shel attended three universities but graduated from none. Here, the story muddles. By his own account, Shel said he attended the University of Illinois at Navy Pier (now known as University of Illinois at Chicago) and was put on probation and then kicked out. Alternately, school records show he actually attended U of I’s Urbana-Champaign campus and successfully completed his freshman year. Friends speculate he changed the story because, at the time, it was rumored the Urbana-Champaign campus was looking to increase its Jewish enrollment, and Shel wanted to be accepted for his talent, not his religion or ethnicity.

For his sophomore year, Shel moved back in with his family in Logan Square and studied at the Chicago Academy of Fine Arts (now the Art Institute of Chicago) in 1949. In 1950, he transferred again to Roosevelt College downtown (now Roosevelt University). According to the Roosevelt University archives, Shel studied English and was a cartoonist and columnist for the school newspaper, The Torch, from 1950-1953. In 1951, Shel started his satirical campus-happenings style column for The Torch called “The Garbage Man,” which was his most well-received work of the time. Shel didn’t plan on finishing his degree, he said, citing that it was better to travel and experience the world than to stay in one place studying it. The U.S. Army ultimately made the decision for him. Shel was drafted in September 1953 and shipped out to Tokyo and Korea.

“In Chicago, I feel guilty if I don’t wake up every morning at nine and carry a lunch bucket.”

During his service with the Army, Shel worked as a journalist for the U.S. Military newspaper, Pacific Stars and Stripes. Once his coverage was well-received by his editors, he also became its cartoonist. His controversial interpretation of life in the Army landed him in trouble—and almost in court. A comic strip in question insinuated that Army officers were stealing uniforms to dress their families. “I said I wouldn’t be so bold as to say something like that,” Shel said in a 1969 interview with Stripes senior writer Hal Drake. “… I said the wife and the kid are dressing G.I. style because they like the Army.” It would have been the world’s first cartoon-related court martial.

All tensions aside, Shel credited the Army for advancing his career. “It did me good,” he said. “Taught me things about life and gave me freedom to create.”

When his two years of service were up in 1955, Shel came back to Chicago hoping to continue work as a cartoonist but he had little luck. “When I was younger I had a stick in my hand and swung it each way,” Shel told Terkel in 1961. “I wasn’t making it, and this was no good and that was no good.”

Unable to secure a cartooning gig, Shel returned to his childhood home and to selling hot dogs at Comiskey. Shel—and his father—quickly grew frustrated. “In Chicago, if you’re an artist or a painter, your family has no respect for you,” Shel said. “In Chicago, I feel guilty if I don’t wake up every morning at nine and carry a lunch bucket. … If you don’t go to work you are a bum in this city and that’s all there is to it.”

It took less than a year for Shel to turn things around. In 1956, he went downtown to seek out a new men’s magazine he knew had recently launched in town. That magazine was Playboy. He strolled in without warning or an appointment. “I walked in and asked to see Hefner, and he was in conference or something,” Shel said. “ … And so I walked around the block in Chicago a couple of times and I found I didn’t have no place else to go so I went back and saw the art director and he took me upstairs to see Hefner, who was in his pajamas.”

They reportedly hit it off, but it would take a month and a follow-up visit before Shel would get paid work. The day his first check cleared, Shel moved out of his parents’ home and started staying with friends throughout the city. He did, naturally, take advantage of staying at the Playboy Mansion, too. “It’s about as swinging a place as anyplace could be,” Shel said.

Playboy soon hired him as its lead cartoonist and picked up a twenty-three-installment pitch. They called it, “Shel Silverstein Visits …”. For the series, Shel traveled around the world, drew a scene, and added a typewriter-style caption. It was later published as a hardcover book in 2007 under the title, “Playboy’s Silverstein Around the World,” with a forward written by Hefner.

While at Playboy, Shel was working on his first—and his most successful—novel, “The Giving Tree.” He finished it in 1960, but it wasn’t until 1964 that he could find a publisher who appreciated the tone of the book. It was seen as too dark for children and too simple for adults. That quality ended up being Shel’s trademark; his recipe for success. “The Giving Tree” has now sold more than five million copies and was named the fourteenth all-time best-selling hardcover children’s book by Publishers Weekly. Of his other best-known works, “A Light in The Attic” spent one hundred eighty-two weeks on the The New York Times bestsellers list and “Where the Sidewalk Ends” was number eleven on Publishers Weekly’s all-time list of hardcover bestsellers.

Shel cared little about success and cared little more about critiques. “I don’t care that much about prestige. I’ve had enough of it to know how little it matters,” he said. He was never surprised by his success either. When asked about “The Giving Tree” in 1975 he said, “What I do is good. I wouldn’t let it out if I didn’t think it was.”

Silverstein-worksThis wasn’t Shel bragging; he was being honest and direct, as he so often was. He was more content with the quality of his work than he was with the work itself. In 1968, he told Drake, his Stripes colleague, plainly he wasn’t satisfied with his work at all. “I have to find change in my work all the time to have any satisfaction. I do better drawing now than I’ve ever done in my life. My drawing is really great now and I’m sick of drawing. So, it isn’t a matter of doing it well. You’ve got to find excitement in it, and that comes from I don’t know what.”
Shel had found work. He’d found success. Still, he was insatiable.

Chicago resident Bob Russell, who lived downtown in the late nineteen sixties, said it was common to see Shel walking about Chicago neighborhoods. “I didn’t ‘know him’ really but I did see him often back in the sixties when I lived on Rush Street, and he was often staying at the Playboy Mansion,” Russell said. “I knew who he was but you saw ‘celebrities’ on the street quite a bit back then and it really wasn’t such a big deal.”

Russell coincidentally bumped into Shel outside of Chicago in 1968, when Shel was living in Key West and Russell was visiting. “I said, ‘We have to stop meeting like this,’ ” Russell remembered. “I don’t remember what he said. I think he just laughed.”

Shel was also known to hang out at Chicago’s first folk club, Gate of Horn, located in the basement of the Rice Hotel (755 N. Dearborn, now a parking lot). Shel wrote that it was “really the social center for the hip crowd” with musicians Bob Gibson and Hamilton Camp as the “social directors.” Shel caught the attention of Gibson when he completed song lyrics for him, and the two soon became close friends. Over the next thirty-five years, they would write more than two hundred songs together. In 1961, “Gibson & Camp Live at the Gate of Horn” was released with liner notes about the club from Shel.

Shel wrote: “ … Gibson and Camp and [Herb] Brown they were up there singing, shouting and playing and stomping and wailing and yelping and barking and dropping raw eggs on the floor … And finally it broke up and everybody went away…they left their carnations laying around on the floor with the raw eggs and that was the end of the old Gate of Horn…and if you missed it you missed something.”

Shel’s music career lived primarily in the country and Western music scene, and he adamantly defended it against its critics. “I love it,” he said. “Again, a lot of people say they hate it when they haven’t even listened to it. You got to listen. Country music isn’t that screaming stuff anymore. There’s good things going on. Good thoughts.”

Shel mastered playing guitar, saxophone, piano, and trombone, and often put his distinct singing to use as a vocalist. “Well, nobody gives me any static about my voice,” he said in a 1978 Chicago Tribune interview. “They just aren’t charmed by it. I don’t see anyone running out and buying my records. But I like the way I sing.”

In addition to his original songs, Shel wrote more than eight hundred songs for others, including Johnny Cash’s hit, “A Boy Named Sue,” which landed Shel a Grammy in 1970. He was also nominated for an Oscar and a Golden Globe for his song “I’m Checkin’ Out” written for the film “Postcards from the Edge.”

The artist he worked with most frequently was Dr. Hook & The Medicine Show (later just Dr. Hook), and he also wrote for country music singers Loretta Lynn, Emmylou Harris, and Waylon Jennings, and the folk group Peter, Paul & Mary.

In a telephone interview with Clay Eals, Steve Goodman said writing lyrics with Shel was like handing in an English class assignment that would come back “corrected … and tremendously improved.” Eals collaborated with Shel as well, and wrote that he was “generous about sharing credit.” So generous that he’d share half the credit if someone came up with just one word that he liked better. “He taught a bunch of us the joys of generosity and how it comes back to you,” Eals said.

Shel was posthumously inducted into the Nashville Songwriters Hall of Fame in 2002.

‘Enter this deserted house / But please walk softly as you do.’
Shel had four homes in the final decades of his life, including a houseboat in Sausalito, California. It was there, in the late sixties, that Shel took Susan Taylor Hastings, the mother of his daughter, Shoshanna. Hastings and Shel reportedly met at the Playboy mansion. Shel, notorious for drawing a strict line between women and his work, never married Hastings and spent little time with Shoshanna. Hastings died four years after Shoshanna was born, and Shoshanna went to stay with her uncle and aunt, Curt and Meg Marshall, in their Baltimore home. According to friends, Shel was too pragmatic, too honest with children to be a father. This, in stunning contrast to his whimsical storytelling, is best illustrated through an anecdote of Shel refusing Shoshanna money from the tooth fairy. He believed in “not sugarcoating the truth to kids.” When Shoshanna threw a fit the morning after losing her first tooth and finding nothing under her pillow, Shel changed his tune. Shoshanna would stay with him for a few weeks during summers, and he’d share his cartoons and stories with her, and she’d give him feedback. Tragically, their relationship was cut short in 1981. Shoshanna, at eleven years old, followed her mother in death, dying of a brain aneurysm. Shel dedicated “A Light in the Attic” to her.

Shortly after, Shel would return to fatherhood. On November 10, 1983, Sarah Spencer, whom Shel met in Key West, gave birth to Shel’s only son, Matthew. Shel met Sarah while she was driving the Conch Train, a tourist trolley on the island, and she was the inspiration for one of his solo songs, “The Great Conch Train Robbery.” Close friends of Shel said that he fully supported Sarah, and that he remained close with both her and Matthew throughout the rest of his life. Matthew was fifteen when his father died. Shel dedicated his poetry collection “Falling Up” (1996) to him.

Shel on the stage
In the nineteen eighties, Shel took to the theatre and wrote more than one hundred one-act plays. Most found a home off-Broadway, including “The Lady or the Tiger” (1981) starring Richard Dreyfuss and a collection of shorts and songs, “The Crate” (1985).

In a 1999 Playbill article following Shel’s death, artistic director Curt Dempster is quoted as saying, “Shel was always a little shy about coming out into the mainstream theatre world, because he didn’t know how to function in it.” His hesitance didn’t show in the final product. Frank Rich, in his The New York Times review of Shel’s 1988 package of plays “Wild Life,” suggested that Shel’s theatre writing “may eventually prove his most fruitful career to date.”

Shel at the Southernmost Point
Shel’s primary residence later in life was Key West, and it’s also where his story ends. His first residence was 525 Caroline Street, just one block east of the touristy strip of bars and clubs on Duval Street. Shel lived on the second level of the home. Now, the home looks more like a college frat house than a landmark. The wooden skin of the house is cracked and peeling. The shutters flap down like eyelids of a local who’s spent too many afternoons under the sun. Shel wrote a song in homage to his landlord at the house, called “Woman Gone Crazy on Caroline Street.” What the walls of the house lack in luster, they make up for with history. Its borders must burst with stories; its shutters surely groan with secrets. There is no signage indicating Shel lived there.
Shel moved off the main drag in 1977 and bought a home at 618 William Street, about a half-mile away. It’s a quieter neighborhood and a single-family home versus rented apartments. There’s a pool in back, and the front is shrouded with banyan trees. Peeking through you can see its painted yellow exterior adorned with delicate white woodwork. It shows a different side of Shel’s personality. We can imagine—or maybe hope—it was a place where he found peace. Or at least, where he worked in peace. Shel bought the home for forty-three thousand dollars in 1977. Its value is now listed at $1.3 million.

Silverstein Homes

Shel was known to perform at the bumper-sticker-and-license-plate-covered Hog’s Breath Saloon in Key West as well as Capt. Tony’s Saloon, where a 1982 photo of him and Capt. Tony still hangs. In Hog’s Breath, the bartenders haven’t been around long enough to have known him—or anyone who may have for that matter. “I know of him but I didn’t know him,” said one of the bartenders, Kim. “He sang? I thought he was an author.” She introduced Brooke, another longtime waitress. “I know he used to live here,” Brooke said. “And I think he wrote some of his poetry down here and about here. Didn’t he die here, too?”

Shel left his mark in different ways throughout town. It seemed he still kept most of who he was a mystery. Shel wasn’t one to conform to a changing world. Maybe that’s why the stories of his later years are lost on modern ears. He never owned a computer and hung on to rotary-style phones. Societal norms never appealed to him either. He believed too many people were obsessed with self-analysis and introspection, telling Terkel that creative types are just “vomiting all the time and collecting it.”

“You’re trying to solve the problems of youth, and then you’re middle aged, and then you’ve got those problems, and then you’re old, and you can’t solve that problem,” he said. “And everybody has problems, and the thing is to function despite these problems and to be a nice person and a good person and a functional creative but a productive person in spite of the problems you have. We all have hang-ups.”

Before Shel died, friends said he was still cartooning, writing, and playing his instruments. “He took extremely good care of himself. Every morning it was yoga, breakfast, and walking,” said his friend Pat Dailey.

His death came as a shock to many who were close to him, who described him as “glowing” in weeks preceding the massive heart attack he would have some time between the evening of May 9 and the morning of May 10, 1999. That morning, Shel was found in bed, surrounded by what he loved most: his poems, his cartoons, and his stories.

His posthumous works are few and far between. Most notably, “Every Thing On It” was published in 2011, twelve years after his death. Mitch Myers, Shel’s nephew and literary executor, told NPR in an interview that Shel never published the work because Shel “wasn’t sure how it would be received.” The book is essentially a collection of his unpublished poems and drawings. “It is and was very different,” Myers told NPR. “And it’s not easy, even for adults to read. I think, actually, younger children have a better time at it because they’re not so preconceived in their notions of how words work.”

In 2009, an event titled “SHELebration: A Tribute to Shel Silverstein” was held in Millennium Park, to honor Shel’s contributions. He was inducted into the Chicago Literary Hall of Fame in 2014.

We have to wonder how Shel would have perceived that attention, that level of acclaim. Shel, like his famous Giving Tree, existed to give, not receive. He was an author for children, a cartoonist for adults, a songwriter of country music, and a talker, joker, and confidant to friends. He could be selfish, and he wasn’t always kind, but he aimed to be honest. He wanted to give—not through himself, but through his work. In 1970, Johnny Cash introduced him on his show with a quote from Harlon Harlow:

“Sometimes he wears a beard and shaves his head. Sometimes he shaves his beard and wears his head. Sometimes he’s writing articles and drawing cartoons for Playboy magazine. He’s in Hollywood working on movies. Sometimes, he’s lonesome. But wherever he is, he’s the one and only Shel Silverstein and one of the most talented guys I ever met.”

Shel isn’t a character anyone could write, except maybe for Shel. For those who kept his poetry on a nightstand in our childhood bedrooms, the story of his own life may be the greatest one he never told.

About the author

Jamie Lynn Ferguson has lived on the west side of Chicago for nearly a decade. She serves as an advocate for anti-poverty nonprofits throughout the city, writes full-time for Catholic Charities Chicago, and is a freelance community reporter for DNAinfo-Chicago.

More From Chicagoly