Shel Silverstein

Growing up in Chicago, Shel Silverstein always planned on being an artist, but he never set out to become an icon of children’s literature. A man of many roles—artist, poet, songwriter, and playwright—he is best known for his light verse and quirky illustrations for young readers. Since the 1960s, generations of children around the world have eagerly sought out his books The Giving Tree, Where the Sidewalk Ends, and A Light in the Attic.

Yet Silverstein started out as a contributor to such adult publications as Playboy, producing illustrations and writing that had a strong libertine bent. He also wrote satirical plays and penned subversive and offbeat country and folk songs. If there was any message in Silverstein’s work, it was to march to one’s own drum. As he once advised his young readers in a poem, “just listen to / The voice that speaks inside.”

The restless young artist

Silverstein was born in 1930 on the northwest side of Chicago. He was the eldest of two children in a close-knit family. His father, Nathan Silverstein, was a Jewish immigrant who owned a bakery with his brother. Shel’s mother, Helen Silverstein (née Balkany), was the Chicago-born daughter of Jewish immigrant grocers.

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From a young age, Silverstein loved drawing, reading, and playing music (his instruments were guitar and saxophone). A lifelong nonconformist, he showed individualistic tendencies early on. Silverstein attended local public schools, but he was often disinterested or distracted in class. On his sixth-grade report card, his teacher noted, “He talks too much” and “Sheldon does not know what obedience means. Take him to hand before it’s too late.” His father expected him to take over the family business someday, but Shel preferred making art to everything else.

After graduating from high school, Silverstein attended the University of Illinois in Urbana-Champaign (1948–49) before transferring to the Chicago Academy of Fine Arts (1949–50) and then Roosevelt College (1950–53; now Roosevelt University). To support himself he worked part-time as a hot dog vendor at Wrigley Field, the home stadium of the Chicago Cubs baseball team (although Silverstein was a White Sox fan). He also freelanced as an artist and illustrator for several publications.

Yet Silverstein was restless during college, later saying, “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.” Although he found a mentor there in his English professor, Robert Cosbey, he left without earning a degree and entered the army in September 1953.

Early career and work for Playboy

While serving in Japan and Korea, Silverstein drew for the military magazine Stars and Stripes and occasionally contributed articles and photographs. In 1955 he published Take Ten, a collection of his Stars and Stripes illustrations. That same year he was discharged from the army, and before long he was also contributing illustrations to Look, Sports Illustrated, and Playboy.

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Unlike much of his later work, Silverstein’s art and writing throughout the 1950s was for an adult audience. In 1956 he returned to Japan as a civilian, kicking off years of travel to such countries as Sweden, England, Russia, Spain, Morocco, and Uganda. At the suggestion of Playboy founder Hugh Hefner, Silverstein documented his travels for the magazine. In later years the travelogue series would include his jaunts to a nudist camp in Pennsylvania, the gay mecca of Fire Island in New York, and the Haight-Ashbury hippie scene in San Francisco. For a couple years he even lived in the Playboy Mansion in Chicago, participating in Hefner’s legendary hedonistic lifestyle. In 1960 Silverstein created the adult book of drawings Now Here’s My Plan: A Book of Futilities before turning to works for children.

Uncle Shelby: The beloved children’s author

Silverstein’s first effort in this direction, written under the name Uncle Shelby, was a satire of children’s alphabet books titled Uncle Shelby’s ABZ Book: A Primer for Tender Young Minds (1961). About this time he also completed a story about a boy and a tree called The Giving Tree, but publishers deemed it too sad for young readers and not quite right for adults. With the help of French artist and author Tomi Ungerer, Silverstein met Ursula Nordstrom, an editor at Harper & Row who encouraged him to seriously pursue writing for children. In 1963 he published his first children’s book, Lafcadio, the Lion Who Shot Back, a modern fable about a lion with an identity crisis. It was dedicated to Cosbey, his college mentor.

Like his later classic children’s books, these early works for children featured Silverstein’s own illustrations. A hands-on perfectionist, he took his art and verse for children seriously, experimenting with different lengths of poems and constantly tweaking and editing his manuscripts to make sure every detail on each page appeared exactly as he wanted it.

In 1964 Silverstein published several children’s books through various publishers, including Who Wants a Cheap Rhinoceros?, Uncle Shelby’s Zoo: Don’t Bump the Glump! and Other Fantasies, and A Giraffe and a Half. The Giving Tree was also released this year, and it eventually became his most famous prose work.

Silverstein, who was often compared to Dr. Seuss, used such locales as the land of Listentoemholler and the castle Now. His first major poetry collection, Where the Sidewalk Ends (1974), featured the popular title verse:

There is a place where the sidewalk ends
And before the street begins,
And there the grass grows soft and white,
And there the sun burns crimson bright,
And there the moon-bird rests from his flight
To cool in the peppermint wind.

His pictures more than complemented his words. Accompanying “The Edge of the World” is the drawing of a small girl peering over the edge of a ledge so thin that a fire hydrant, a dog, a signpost, and a worm protrude halfway through. The cover of A Light in the Attic (1981) shows a boy with a windowed attic forming the top of his head. The words of another poem form the neck of a giraffe. Silverstein released album recordings of Where the Sidewalk Ends and A Light in the Attic in 1984 and 1985, respectively; they feature him reading his poems, some with musical accompaniment. The album Where the Sidewalk Ends won a Grammy Award for best recording for children.

Silverstein often eschewed happy endings because children, he said, might otherwise wonder why they themselves were not comparably happy. In The Giving Tree, for example, the tree literally gives the boy all she has—her apples, branches, and trunk—until she is reduced to a stump. Some readers view the story as a metaphor for the unconditional love of parenting, and some have called the relationship between the characters unhealthy. But Silverstein rejected such moralistic interpretations. Indeed, critics have noted that many of his works end ambiguously, allowing readers to come to their own conclusions and draw their own wisdom from the story.

Silverstein has also been credited with helping young readers develop an appreciation of poetry, and his serious verse reveals an understanding of common childhood anxieties and wishes. His poem “Whatif,” for example, features a list of a child’s fears (“Whatif I’m dumb in school? / Whatif they’ve closed the swimming pool?”) that, while humorous, offers no judgment of the young speaker. Other poems address such topics as loneliness, creativity (as in the immortal line, “Put something silly in the world”), sibling rivalry, and the tedium of chores (as in “Sarah Cynthia Sylvia Stout Would Not Take the Garbage Out” and the subversive “How Not to Have to Dry the Dishes”). Among his other books are The Missing Piece (1976) and The Missing Piece Meets the Big O (1981), which feature a partial circle as their memorable protagonist.

Songwriting career: Among the outlaws

A lover of country music, Silverstein spent a lot of time in Nashville among the outlaw country scene, where he found kindred spirits among such songwriters and musicians as Kris Kristofferson and Waylon Jennings. The outlaw musicians rebelled against the formulaic country music of the day, much as Silverstein rebelled against many conventions in children’s literature—and against societal conventions in general. Inevitably, he collaborated with many of these musicians.

His songwriting career officially began in 1959 with the release of his first album, Hairy Jazz. Many other recordings followed, including Inside Folk Songs (1962), I’m So Good That I Don’t Have to Brag (1965), Freakin’ at the Freakers Ball (1972), and The Great Conch Train Robbery (1980). Like his verse, many of Silverstein’s songs are wry and irreverent, ranging from novelty tunes to relatable story songs and ballads that captured the countercultural zeitgeist of the 1960s and ’70s. However, his most famous songs were covered by other artists, including:

• “The Unicorn,” recorded by the Irish Rovers in 1967
• “A Boy Named Sue,” first performed and recorded by Johnny Cash in 1969 at a concert at San Quentin State Prison in California and the winner of the Grammy for best country song in 1970
• “One’s on the Way,” recorded by Loretta Lynn in 1971
• “Cover of the Rolling Stone,” recorded by Dr. Hook and the Medicine Show in 1972 and heard in the film Almost Famous (2000)
• “The Ballad of Lucy Jordan,” recorded by Marianne Faithfull in 1979 and featured on the soundtrack of the film Thelma & Louise (1991)
• “I’m Checkin’ Out,” performed by Meryl Streep in the film Postcards from the Edge (1990) and nominated for an Academy Award and a Golden Globe for best original song

Silverstein’s other notable musical projects include composing the soundtrack for the film Ned Kelly (1970; best remembered as rocker Mick Jagger’s acting debut) and collaborating with country singer Bobby Bare on the album Sings Lullabys, Legends and Lies (1973). In 1998 Bare teamed with Jennings, Jerry Reed, and Mel Tillis to record more of Silverstein’s songs for the album Old Dogs.

Plays, later life, and posthumous works

Silverstein also wrote one-act plays, sometimes working with David Mamet. In 1983 his play Gorilla debuted at the Goodman Theatre in Chicago (alongside plays by Mamet and Elaine May), and Silverstein won a Jeff Award (which recognizes achievement in Chicago theater) for outstanding new work. In 1988 he collaborated with Mamet on the screenplay for the crime comedy-drama Things Change, which was nominated for an Edgar Award for best motion picture.

As an adult, Silverstein moved often, making his home in New York City; Sausalito, California; Martha’s Vineyard on the East Coast; and Key West, Florida, where he spent the last years of his life. In Key West he was part of the same social circle as fellow local legend Jimmy Buffett (of “Margaritaville” fame), although the two men never collaborated as songwriters. Falling Up (1996) was Silverstein’s last illustrated collection, published before his death from a heart attack in 1999.

Runny Babbit: A Billy Sook (2005), Every Thing On It (2011), and Runny Babbit Returns (2017) are among his posthumously released children’s works. In addition, anniversary editions of Where the Sidewalk Ends (published in 2004), A Light in the Attic (2009), and Falling Up (2014) featured many new poems. Silverstein’s travel pieces for Playboy are collected in Silverstein Around the World (2007).

Honors and personal life

Silverstein’s honors include his induction into the Nashville Songwriters Hall of Fame in 2002 and the Chicago Literary Hall of Fame in 2014. He was given the Poet’s Award by the Academy of Country Music in 2017.

Silverstein never married, but he was the father of two children: daughter Shoshanna and son Matt. In 1982 his daughter died from a brain aneurysm at age 11.

In 2017 Silverstein’s historic home in Key West was badly damaged by Hurricane Irma. Although it was demolished (and the banyan “Giving Tree” was uprooted), the owners eventually built an exact replica of the home. Silverstein’s archives, including the extensive book and record collections he gathered throughout his life, are located in his hometown of Chicago, where they are managed by his family.