The children’s book author and Playboy illustrator Shel Silverstein was not known to be particularly studious during his days attending Darwin Elementary School in Chicago’s Logan Square.

Instead, he had a tendency to doodle, officials said Friday at a ceremony hosted by Chicago Public Schools and the United States Postal Service to unveil and dedicate the Shel Silverstein Forever Stamp.

Educators said the notable 20th century author and artist can be an example for the current generation of Chicago students.

“Just like you, Shel Silverstein was a student here at Darwin. His success tells us that any one of you could grow up to make this kind of mark on the world,” CPS Chief of Schools William Klee told the students in the audience. “Your legacy could one day appear on a Forever Stamp like the one we’re celebrating today.”

Silverstein, who was born in Chicago in 1930, authored more than 20 books — writing everything from the collection of poetry and drawings Where the Sidewalk Ends to Johnny Cash’s hit song, “A Boy Named Sue.” The stamp, now for sale, features artwork from Silverstein’s classic 1964 story, The Giving Tree.

The bright green stamp depicts the book’s lead character with his arms outstretched for a falling apple, an image that will resonate with many children and parents familiar with the book. The stamp calls upon Silverstein’s “deceptively simple story” about a friendship between a boy and a tree to symbolize his life’s work, said Judy de Torok, the Postal Service’s vice president of corporate affairs.

“[Silverstein] could be silly or serious and anything in between. With his witty rhymes and whimsical, nonsensical verse, it was clear that he loved to play with language. It was also clear that his many readers ⁠— young and old alike ⁠— loved him for his clever word play,” de Torok said.

A crowd of about 100 people gathered at Friday’s ceremony, where elementary students recited some of Silverstein’s poems and showed off new Giving Tree-themed artwork in the hallways.

While his legacy is often synonymous with children’s literature, Silverstein did not set out to write for kids.

“He worked for Playboy and wrote raunchy songs for rock bands,” said artist and author Dmitry Samarov. “He only turned to art and writing at all once it became clear he wouldn’t be in the starting lineup for his beloved White Sox, though he did sell hot dogs at Comiskey Park [for a bit].”

Despite the hometown pride on full display, Silverstein spent his adult years living elsewhere. He died in 1999 at his Key West home.

Other 2022 USPS stamp honorees include sculptor Edmonia Lewis, musician Pete Seeger and the first female publisher of the Washington Post, Katharine Graham. Silverstein joins other famous Chicagoans such as Gwendolyn Brooks and Jean Baptiste Point du Sable who have been honored on stamps in the past.

Courtney Kueppers is a digital producer/reporter at WBEZ. Follow her @cmkueppers.