Shel Silverstein, Playboy
Shel Silverstein was a legendary American artist known best for his children’s books including The Giving Tree, Where the Sidewalk Ends, and A Light in the Attic. Silverstein was born in Chicago in 1930 and would eventually join the military in the early 1950s. While serving in the U.S. Army, he was a cartoonist for Pacific Stars and Stripes, a daily newspaper published for members of the armed forces.
“For a guy my age and with my limited experience to suddenly have to turn out cartoons on a day to day deadline, the job was enormous. It was a great opportunity for me and I blossomed,” Silverstein said about the start of his cartooning career in a 1969 interview with Stars and Stripes.
Early on in his cartooning career, Silverstein was given the opportunity to cartoon for Hugh Hefner’s Playboy Magazine a few years after the magazine ran its first issue. Not long after his introduction to Playboy (first appearing in 1956 just three years after the first issue) Silverstein became by far one of the most popular contributors. As a matter of fact, according to Playboy, Shel Silverstein’s contributions became the second most popular Playboy feature behind only the centerfolds.
This was Silverstein’s first contribution to Playboy, which was from the August 1956 issue.
Silverstein’s first few years with the magazine were collected and published as a now out of print book called Around the World, which has become a little bit of a collectible now. This collection is primarily his cartoons and sketches of his time traveling around the world and observing himself within different places and cultures.
Looking into Shel Silverstein has made it clear to me that he was an incredibly significant figure in the counter-culture movement of the 1960s. His work was very popular at the time and he had his hands in all sorts of work during the cultural movement. He was sometimes referred to as “Uncle Shelby,” and under this name he wrote Johnny Cash’s “A Boy Named Sue.” In addition to writing songs for Johnny Cash, he also wrote hit songs for Dr. Hook, Loretta Lynn, Tompall Glaser, and Waylon Jennings. This was a fascinating part of Silverstein’s legacy and his music career is interesting enough on its own since he won a Grammy award and was nominated for both an Academy Award and Golden Globe.
Shel Silverstein and Johnny Cash performing “A Boy Named Sue” on The Johnny Cash Show in 1970.
Playboy was arguably the most popular counter culture magazine at the time, and many credit it with being the first to discuss taboo and adult topics. Many of Silverstein’s contributions allude to the sexual revolution and the hippie culture specifically in the 1960s and the 1970s.
This section is from Silverstein’s “Among the Hippies” which was from Playboy’s July 1968 issue.
Once Hugh Hefner acquired the famous Playboy Mansion in Chicago and later Los Angeles, the door to a new lifestyle would open for Silverstein. Uncle Shelby would spend weeks to months at a time on long extended stays, and would become a very close friend to Hefner. He became addicted to the infamous Playboy lifestyle all the way until his death in 1999.
Shel Silverstein and Hugh Hefner at the mansion. Taken from Hugh Hefner’s Twitter account.
Finding out a children’s author or artist has done work for an adult audience and demographic is always so interesting because you get to observe a different perspective on an art style you have grown up with. The subject matter throughout Shel’s Playboy career is particularly interesting to me because the counter-culture of the 1960s and the change in society it brought is cool to learn about. I enjoy that I can visit Silverstein’s work with more mature subject matter and have a sense of nostalgia.
This was an illustration from the final Silverstein contribution to the magazine while he was still alive, a poem called, “Hamlet as Told on the Street.” From the January 1998 issue.
Silverstein’s final contribution to Playboy Magazine. A short story with illustrations written in 1993 called “Topless Town,” was posthumously published in the January 2001 issue.
Shel Silverstein’s adult oriented content is definitely worth checking out especially if you are familiar with his children’s books since it is a fascinating side to the artist’s history. For over 40 years (1956 to 1998) Silverstein made contributions to Playboy that played an important role in documenting the counter-culture of the 1960s while simultaneously becoming a beloved children’s author. His work will continue to make people laugh at the oddities and absurdity of everyday life.