When I am gone what will you do? Who will write and draw for you? Someone smarter–someone new? Someone better–maybe YOU!

“When I Am Gone” by Shel Silverstein

Sheldon Allan Silverstein was born September 25th, 1930, in Chicago Illinois. His father ran a bakery and expected Sheldon, who was born at the beginning of the Great Depression, to take over the family business. 

After graduating from Roosevelt High School the young Silverstein attended the University of Illinois, but was expelled due to poor grades. He then went to the School of the Art Institute of Chicago, but dropped out, and in the Spring of 1950 enrolled at Roosevelt College. There he contributed cartoons for the student newspaper, the first of which depicted a naked co-ed (male) smoking a cigarette, standing up to the professor “What do you mean, ‘No Smoking?’ I thought this was a LIBERAL school.” Throughout his educational career Silverstein was described as a poor student who hated conformity. 

In 1953 he was drafted into the US Army during the Korean War, and went to serve in Japan and Korea, where he became a journalist and cartoonist for the military newspaper. Not surprisingly, he was nearly court-martialed for one of his cartoons. In 1955 a compilation of his military cartoons was published by Pacific Stars and Stripes as Take Ten. It was republished in 1956 as Grab Your Socks! by Ballantine Books.

After being discharged from the Army in 1955 he became a freelance cartoonist, getting some jobs for Sports Illustrated and Look, and while also selling hotdogs. In 1956 he began working for Playboy, first drawing cartoons, and then traveling the world as Playboy’s cartoon-drawing foreign correspondent. His travelogue soon became the magazine’s second most popular feature. Silverstein mused that as a child all he wanted was to play ball and be popular with girls, but could do neither – so he drew. The talent he developed later made him very popular with the girls, and he became a fixture at the Playboy mansion. 

In 1960 a cartoon collection featuring his most famous cartoon – Now Here’s My Plan – was published by Simon & Schuster. 

Another grown up humor book – Uncle Shelby’s ABZ Book: A Primer for Tender Young Minds was published in 1961 by Simon & Schuster.

In 1963, at age 32, Silverstein published his first children’s book, Uncle Shelby’s Story of Lafcadio, the Lion Who Shot Back.  (Uncle Shelby was a pen name he used).

His most popular book, The Giving Tree, took four years to find a publisher before it was finally published in 1964. Most editors rejected it as being too depressing for children. 

Most sources say the Silverstein never married, and according to his 2007 biography A Boy Named Shel he slept with hundreds, if not thousands of women. Whether or not he married, he did have a few notable relationships, and two children.

Silverstein met Susan Taylor Hastings at the playboy mansion. They had one daughter, Shoshanna, born on June 30th, 1970, and were reportedly together until Susan’s death on June 29, 1975, the day before their daughter’s fifth birthday. After Susan’s death Silverstein sent Shoshanna away to live with an aunt and uncle, and Shoshanna died at the age of 11, on April 24, 1982 from a cerebral hemorrhage. Silverstein had dedicated his 1981 book, A Light in the Attic to her. 

While living in Key West Silverstein met Sarah Spencer, a Key West native who drove a tourist train. On November 10, 1984 their son Matthew De Ver was born. Silverstein was 54 at the time. 

Another of Silverstein’s incredibly popular children’s poetry books, Where the Sidewalk Ends, was published in 1974. His children’s books sold more than 20 million copies.

In addition to drawing comics and writing children’s books, Silverstein wrote over 800 songs and released 9 music albums. Many of his songs were written for other artists, including Dr. Hook & The Medicine Show, and Loretta Lynn. Silverstein wrote one of Johnny Cash’s biggest hits “A Boy named Sue,”  which won a Grammy in 1970. He also co-wrote “The Taker” with Kris Kristofferson, recorded by Waylon Jennings. His songs have been used in many TV shows and movies, including “The Cover of Rolling Stone” in Almost Famous and “The Ballad of Lucy Jordan” from Thelma & Louise. 

Silverstein died on May 10, 1999 of a heart attack at his home in Key West, Florida. He was 68 years old. He is buried in Norridge Illinois. 

Lesson from Silverstein

If you ask most people, they would not know Shel Silverstein started out his writing career living his best life at the Playboy Mansion and writing articles to compete with centerfolds of boobies. He’s best remembered for his irreverent and fun poems and lovely sad stories that showed generations of children that poetry did not have to be hard or boring. Maybe he was good at that simply because he himself chose to a live a life that wasn’t hard or boring either.

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