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This article originally appeared in mental_floss magazine.

by Mark Peters

Shel Silverstein—the late cartoonist, singer, songwriter, playwright, and mega-selling author of such classics as The Giving Tree and Where the Sidewalk Ends—didn’t like children’s literature. Spoon-feeding kids sugar-sweet stories just wasn’t his style. Fortunately for generations of young readers, someone convinced him to do something about it—namely, break the mold himself. Using edgy humor, clever rhymes, and tripped-out drawings, Silverstein achieved the impossible. He bridged the worlds of adult and children’s art, while becoming wildly popular in the process.

Where the Sidewalk Began

Sheldon Allan Silverstein was born on September 25, 1930, into a Jewish middle-class family in Chicago’s Logan Square neighborhood. And though the intensely private Silverstein never divulged many details of his youth, we do know his childhood was largely consumed with a rabid devotion to the Chicago White Sox. In fact, if the cartoonist-in-training could’ve belted homers instead of scrawling pictures, he definitely would have. Instead, the unathletic young Silverstein had to settle for filling up sketch pads instead of stat sheets.

Silverstein’s skills in the classroom didn’t fare much better than they did on the field. After brief stints at the University of Illinois at Urbana (where he was thrown out) and the School of the Art Institute of Chicago (where he dropped out), Silverstein managed to last three years at Chicago’s Roosevelt University, where he studied English. More significantly, however, that’s where he began writing and cartooning for the student paper, The Torch, whereby he launched his lifelong career in skewering authority figures.

His first published cartoon, for instance, was that of a naked student holding a cigarette while confronting a peeved professor. The caption read, “What do you mean ‘No Smoking’? I thought this was a liberal school.”

Aside from receiving a little artistic encouragement at Roosevelt, Silverstein didn’t exactly get a lot out of college. Summing up the experience, he once said, “I didn’t get laid much. I didn’t learn much. Those are the two worst things that can happen to a guy.” Silverstein was drafted in 1953, before he had the chance to finish school (though he’s not convinced he would have) and was shipped off to serve in the Korean War. His tour of duty likely influenced his often-dark worldview, but it definitely shaped his emerging career path. Oddly enough, Silverstein earned his first art-related paychecks as a journalist and cartoonist for the Pacific edition of the U.S. military’s newspaper, Stars and Stripes. Despite the rigid environment, he couldn’t resist the urge to rib the powers-that-be in his work. In fact, Silverstein narrowly avoided the world’s first cartoon-related court martial over a comic strip that seemed to imply officers were dressing their families in stolen uniforms. This led to stern instructions that only civilians and animals were proper topics for criticism.

Although not exactly a “yay, military!” kind of fellow, Silverstein nevertheless appreciated the opportunities the Army gave him to travel and hone his craft. After being discharged in 1955, he returned to Chicago and started cartooning on a freelance basis. His hard work soon paid off, and Silverstein started landing gigs at magazines such as Look, Sports Illustrated, and This Week. But then he hit the jackpot; he met Hugh Hefner and got in on the almost-ground floor of Playboy, which had premiered just two years prior. From 1956 on, Silverstein was known to live intermittently with his new pal at the Playboy mansion while contributing articles, as well as plenty of not-quite-kid-friendly comic strips.

Kids’ Authors Say the Darnedest Things

Given the whole Playboy thing, Shel Silverstein was hardly a prime candidate to become the world’s next great children’s author. After all, the guy wasn’t shy about his distaste for the genre—a fact evident in his 1961 book, Uncle Shelby’s ABZ Book: A Primer for Tender Young Minds. Excerpted in Playboy, the adult book spoofed the Dick-and-Jane genre with lines such as “See the baby play. / Play, baby, play. / Pretty, pretty baby. / Mommy loves the baby / More than she loves you.” The ABZ Book made it clear that Silverstein hated the condescending brand of writing often used in children’s literature—and what better way to change the state of affairs than to write them better yourself? Convincing Silverstein of that took a fair amount of wheedling and cajoling, but his friend (and children’s author/illustrator) Tomi Ungerer, along with famed Harper & Row children’s editor Ursula Nordstrom, was up to the task. Eventually, they persuaded Uncle Shelby to take a crack at the real thing.

In 1963, at age 32, Silverstein published his first children’s book, Uncle Shelby’s Story of Lafcadio, the Lion Who Shot Back. The tale—in appropriately Silverstein-twisted fashion—is about a marshmallow-loving lion who faces an identity crisis after becoming a celebrated marksman. It was a huge hit. By 1974, Lafcadio had plenty of company, including Uncle Shelby’s A Giraffe and a Half, Who Wants a Cheap Rhinoceros? and two books that would eventually rank among the 20 bestselling children’s books of all time: The Giving Tree and Where the Sidewalk Ends (hereafter shortened to Sidewalk).

Poem-cum-cartoon collections such as Sidewalk (and, later, A Light in the Attic and Falling Up) became instant classics for obvious reasons. They featured Silverstein’s trademark giddy style and his unmistakable talent for crafting verses as pliable as putty. Who else can write lines like, “Washable Mendable / Highly dependable / Buyable Bakeable / Always available / Bounceable Shakable / Almost unbreakable / Twistable Turnable Man”? Silverstein also endeared himself to readers with unpretentious language, loony black-and-white drawings, and memorable characters (Sarah Cynthia Sylvia Stout from Sidewalk’s “Sarah Cynthia Sylvia Stout Would Not take the Garbage Out” comes to mind).

For all of these reasons, Silverstein’s work was tremendously well received by the masses.

However, anytime you push an envelope, you’re bound to take some heat. Indeed, both Sidewalk and A Light in the Attic were banned from various libraries and targeted by prudish groups who thought the poems and pictures were too weird, too gross, too antiauthoritarian, or otherwise too much for children’s fragile minds.

In fact, opponents called Silverstein’s poems everything from Satanic and sexual to anti-Christian and cannibalistic. Yes, cannibalistic.

Apparently, some folks took serious issue with Sidewalk’s poem “Dreadful,” which contained such verses as “Someone ate the baby. / What a frightful thing to eat! / Someone ate the baby / Though she wasn’t very sweet. / It was a heartless thing to do. / The policemen haven’t got a clue. / I simply can’t imagine who / Would go and (burp) eat the baby.” The eating-human-babies fad never really caught on in America, but perhaps protesters stopped the madness just in time.

Grim Reaping

Those who branded Silverstein’s work as unfit for children were certainly extremists, but that’s not to say Uncle Shelby didn’t have a dark side that could be a bit unnerving at times. There are hints of this even in The Giving Tree, which tells the story of a generous tree that repeatedly donates parts of itself to a needy boy until it’s nothing more than a stump. Although the book is considered a classic today, after Silverstein finished it in 1960, it took him four years before he found anyone willing to publish it. Apparently, editors found it too depressing for kids and too simple for adults. It wasn’t until his other titles started raking in the dough that Harper & Row was confident enough to give it a shot.

Other times, however, it’s much more obvious that Silverstein had no qualms writing children’s literature that was less than shiny and happy. Probably the best example is 1964’s Who Wants a Cheap Rhinoceros? In it, a boy lists numerous reasons why a priced-to-sell rhino would make a sound investment, including “He can open soda cans for your uncle” and “He is great at imitating a shark.” Gradually, however, the lines get a lot less goofy. On one page, the boy describes the rhino as “good for yelling at,” which is accompanied by a picture of the abject, tearful pet. Another page suggests the rhino is “great for not letting your mother hit you when you really haven’t done anything bad.”

Lines such as those are particularly shocking, but they ultimately reflect one of the most innovative aspects of Silverstein’s work—a sense of mutual respect and honesty often lacking in children’s literature. Silverstein firmly rejected the notion that characters should always ride off into a sunset or that kids should be taught to aspire to an all-rosy-all-the-time life. In fact, one of his greatest impacts on the genre was proving that creating great children’s literature doesn’t always mean treating your readers like kids. But Silverstein perhaps summed up his philosophy best in “The Land of Happy” from Sidewalk: “There’s no one unhappy in Happy / There’s laughter and smiles galore. / I have been to the Land of Happy— / What a bore!”

The Silver Lining, Shel-Style

Silverstein’s desire to reverse dopey endings and shiny-happy storylines may have been simply a result of his distaste for predictability. In his art as well as his life, Silverstein strenuously avoided well-trod paths. “Successful cartoonist becomes immortal children’s author” is a pretty straightforward tale, so leave it to Shel to throw in the occasional Playboy monkey wrench. Similarly, Silverstein made it pretty impossible to get pigeon-holed into a poetry-and-cartooning rut by simply tossing in a few other careers on top—songwriter, musician, novelist, you name it.

In 1959, just a few years before he started to write children’s books, Silverstein began a respectable career in music. How respectable? Well, he was inducted into the Nashville Songwriter’s Hall of Fame, won two Grammy awards, recorded more than a dozen albums, and wrote hundreds of songs that were recorded by artists including Kris Kristofferson, Waylon Jennings, and Jerry Lee Lewis. The poetry skills Silverstein brought to children’s books were easily parlayed into a knack for clever songwriting. And while Silverstein didn’t have the voice to make it as a performer, he quickly attracted attention from other musicians eager to record his tunes (many of which can be found on the recently released The Best of Shel Silverstein: His Words His Songs His Friends). Of course, it helped that Silverstein was considered an exceedingly generous collaborator. He was popularly known for his policy of giving equal credit to anyone who co-wrote a song with him, even if they contributed only a single line or small idea.

What’s interesting is that this was the polar opposite of Silverstein’s reputation in the world of literature. One reason his books are so easy to spot on a bookshelf is that he made unyielding demands about their formats. Most have never been printed in paperback (per his instruction), and he scrupulously selected every typeface and paper grade. Such micromanagement might have benefited him as an author, but in the music industry, his generosity paid off, freeing him from petty monetary squabbles and making him an even more appealing collaborator. And plenty lined up to work with Shel. Silverstein-penned hits include The Irish Rovers’ “The Unicorn,” Loretta Lynn’s “One’s On the Way,” Dr. Hook and the Medicine Show’s “Sylvia’s Mother” and “Cover of the Rolling Stone,” and, of course, Johnny Cash’s “A Boy Named Sue.”

On top of all that, Silverstein was more than a dabbler in the dramatic. He wrote dozens of plays that were well-received by critics, including The Devil and Billy Markham, The Crate, The Lady or the Tiger Show, Gorilla, and Little Feet, plus the screenplay for Things Change with playwright pal David Mamet. His musical talents also carried over to several movie soundtracks, including an Oscar-nominated song from Postcards on the Edge. On the side, he did a little acting, most notably a small role in Who Is Harry Kellerman and Why is He Saying Those Terrible Things About Me? alongside Dustin Hoffman. Not bad for something that probably would’ve appeared on the ninth page of his resume. Of course, that wasn’t everything. In his abundant spare time, Silverstein penned a few mystery stories. We also heard he sculpted a few statues, choreographed a ballet, and built an Egyptian-style pyramid, but there’s no truth to those stories. As far as we know.

Crying Uncle

Silverstein once said, “Don’t be dependent on anyone else—man, woman, child, or dog. I want to go everywhere, look at and listen to everything. You can go crazy with some of the wonderful stuff there is in life.” Restless words from a restless man. Throughout his life, Silverstein didn’t stay with a single art form, or live at a single residence, for too long. The same philosophy also seemed to apply to his love life. He had two kids, but never married. Freedom of all sorts—especially the freedom to create what, when, and however he wanted—was vital to him. Such an idiosyncratic path doesn’t often lead to big bucks, but Shel was once again the exception to the rule. When he died of heart failure on May 10, 1999, at the age of 68, he was worth millions.

Silverstein gave only a few interviews during his lifetime, and not many were lengthy. He seems to have had a real aversion to blabbing about his work. In fact, he didn’t even like for his stuff to be advertised, asking that excerpts of poems and cartoons be the sole contents of any necessary, evil, and publisher-mandated publicity. He once suggested, “If you want to find out what a writer or a cartoonist really feels, look at his work.” We can only recommend you simply trust him on that one.