Shel Silverstein was an irrepressible creative spirit and globetrotting troubadour who traveled around Europe, Asia, and Africa and wrote whenever inspiration hit—in notebooks, on napkins, restaurant placemats, and paper bags. Born in Chicago in 1930, the children’s book author, illustrator, cartoonist, poet, playwright, and songwriter created endearing classics like The Giving Tree, A Giraffe and a Half, Don’t Bump the Glump!, and Who Wants a Cheap Rhinoceros?, all of which celebrated their 60th anniversaries in 2024, and Where the Sidewalk Ends, which turned 50. His books have sold 50 million copies worldwide, according to HarperCollins, and have been translated into 50 languages.

Silverstein seemed to walk through life with a lightbulb of bright ideas shining over his head—and when he died in 1999, he left behind a trove of notebooks, sketches, and musical recordings spread across homes in New York City, Key West, Martha’s Vineyard, and Sausalito. These documents, and some of his possessions (library cards, decorative wood masks, rugs, and paintings), are housed at the Shel Silverstein Archives in Chicago. This repository of his work is managed by Silverstein’s nephew, Mitch Myers, a music journalist, and Silverstein’s niece, Liz Myers, a yoga instructor and Mitch’s sister—with assistance from senior archivist Joy Kingsolver, who’s been working on the archive since 2002, and associate archivist Greg Pearson. “When Shel died, we were all crushed,” Mitch said of the family, which also includes Silverstein’s sister and his son, among others. “The archive bought us together.”

PW was recently invited by the Silverstein family for an exclusive tour of the Shel Silverstein Archives—which are closed to the public. Mitch and Liz were there, along with Kingsolver, to give the tour. The Archives are located on an unremarkable street across from a trucking company, on the sixth floor of a fortress-like warehouse used to store fine art for museums, auction houses, and private collectors. It’s not much to look at from outside, but stepping into the 6,000-square- foot, climate-controlled space is like walking into the colorful mind of Silverstein himself. There are shelves stacked with boxes filled with pages of Silverstein’s playful and poignant prose, some with handwritten editorial notes in the margins; sketches; and works-in-progress. On display on a table is his tattered sketchbook, open to a draft of “Sarah Cynthia Sylvia Stout Would Not Take the Garbage Out” from Where the Sidewalk Ends, which has Wite-Out marks and his original drawings; and a paste-up of “What if?” from A Light in the Attic, which features his scribbled corrections in pen, and drawings of a walking carrot and teapot glued to the page, and is an example of how Silverstein adjusted his work before it went to press. There’s a media room with his records and guitars (“He was an elementary musician,” Mitch said of Silverstein, who wrote hit songs for Johnny Cash (“A Boy Named Sue”) and Loretta Lynn, but “he knew three chords, no doubt!”); rows of beat-up paperbacks salvaged from his houseboat in Sausalito (he liked sci-fi stories); and his extraordinary personal collection of children’s books, featuring copies of The Wizard of Oz and Charlotte’s Web; books of Ukrainian and Romanian folktales; and many rare and first editions, including board books from the 1910s.

Growing up, the Myers siblings were close to Silverstein—a cool uncle who asked for their opinions on his work and encouraged them to pursue their dreams, and who always collected books. “He didn’t drive,” Liz recalled. “He’d walk from one used bookstore to the next and have them send books to his house.” She grew emotional as she reflected on his impact. “I don’t know if I have anybody like that in my life now who loves to try new things as much as he did. He loved experiencing life.”

Like his peers Maurice Sendak and Dr. Seuss, Silverstein had strong opinions on children’s literature and didn’t want to fill kids’ heads with happy endings that didn’t mirror real life. Organizing his papers and creating and maintaining a database of his work has been an exciting, decades-long challenge for softspoken archivist Kingsolver, who’s a whiz at remembering what’s where. “I like to create order,” she said. “Anything Shel saw was inspiration to create. The archive shows his creative process and how things flowed out of him.”

Keeping Silverstein’s work alive and introducing it to new generations is important to his family—as is Silverstein’s wish to only have his books published in hardcover. In the last years, the family have worked to digitize his music catalogue. He released more than 500 songs, which he either wrote or co-wrote—tunes that over time have been re-recorded by musicians around the world. He also wrote hundreds of songs that have never been released.

In addition to working on the music catalogue, the family have overseen the release of e-books of his classics, as well as three posthumous books (Runny Babbit, Runny Babbit Returns, and Everything on It). They’re also planning to put out audiobooks and primers for young readers in the future.

Alyson Day, Silverstein’s editor at HarperCollins, who worked on Runny Babbit Returns and Everything on It, has known the family professionally since 2008. A lifelong Silverstein fan, she still has her childhood copy of A Light in the Attic. “Shel found humor in both light and dark moments,” said Day. “He had a grand, zany sensibility that really touches on your soul.”

The family are proud to be custodians of Silverstein’s legacy. “Shel tried to speak to children on a one-to-one level,” Mitch said. “He wanted kids to believe in themselves and to follow their inner voice.” Silverstein followed his voice, too—and his archive is a tribute to his circuitous artistic journey.

Elaine Szewczyk’s writing has appeared in McSweeney’s and other publications. She’s the author of the novel I’m with Stupid.