Shel Silverstein

Little is known about Silverstein’s personal life. It is possible that he never actually got married, but had a partnership with Susan Taylor Hastings of Sausalito, California, with whom he fathered a child named Shoshanna Jordan Hastings, born on June 30, 1970.

Susan died in 1975, five years after the birth of their daughter. Six years later, on April 24, 1982, Shoshanna too died from cerebral aneurysm. She was then eleven years old.

Silverstein also had a son named Matthew, born on November 10, 1984, out of a liaison with Sarah Spencer, a conch train driver from Key West, Florida. Nothing else is known about them.

Shel Silverstein was born on September 25, 1930, in Palmer Square, a middle class neighborhood located within the Logan Square area of Chicago, Illinois. Both his parents, Nathan and Helen Silverstein, were of European descent.

Nathan Silverstein, a first-generation immigrant, was the co-owner of a bakery called Silverstein Brothers, which he ran with his elder brother, Jack Silverstein, at Walton Street. Later in 1930, as the business grew, the bakery was shifted to a larger premise on N. Western Avenue and renamed as Service Cake Company.

Shel was the elder of his parents’ two children, having a sister called Peggy, four years his junior. At the time of his birth, his parents lived with Helen’s mother at 1458 North Washtenaw. Her sister and brother-in-law also lived in the same house.

Living in an extended family, Shel was raised in a noisy environment. Other families living in the apartment building were equally boisterous. Clomping up and down the stairs, they very often knocked into see how the family was doing. The road downstairs was another source of the chaos.

The greatest source of their hardship was the Great Depression that started in 1929. By then, his father had invested a lot of money in acquiring a bigger commercial space. Soon, they started feeling the pinch. For dinner; they mostly had one-day old bread and pastries brought home by Nathan.

As he joined the United States Army, Silverstein was sent to the Far East, to serve in Japan and Korea. Here he was assigned to do layouts and paste-up in the military newspaper ‘Pacific Stars and Stripes’. Slowly, he also started submitting cartoons.

Although many of the cartoons offended the oversensitive military bosses, they were published in the newspaper, albeit after some censoring. His first book, ‘Take Ten’, published in 1955 by Pacific Stars and Stripes, was a compilation of the Take Ten cartoon series that he created during this period.

After being released from the military service, he returned to Chicago and started submitting cartoons to various papers, all the while selling hot dogs at Chicago parks for his upkeep. Slowly, his cartoons began to appear in well-known journals like Look, Sports Illustrated and This Week.

His break came in 1956, when ‘Take Ten’ was republished by Baltimore Books as ‘Grab Your Socks’. The book introduced him to the general public and was much appreciated by them.

In 1956, Shel Silverstein was introduced to Hugh Hefner, publisher of Playboy magazine, who offered him the post of a cartoonist. A savvy cartoon director, Hefner allowed Silverstein go as naughty and racy as he wished.

By 1957, Silverstein, flourishing under Hefner’s direction, became the leading cartoonist at Playboy. With the success, came more challenging assignments. Hefner now sent him to far-flung areas in and outside USA for creating an illustrated travel journal.

In course of his travel, Silverstein visited the nudist colony of New Jersey, Haight-Ashbury district in San Francisco, White Sox training Camp in Chicago etc. He also visited Latin American countries like Cuba, Mexico, different countries in Africa, and European countries like England, France and Switzerland. In Cuba, he interviewed Fidel Castro.

From the places he visited, he sent comically captioned photos, unorthodox illustrations and poems; in all producing 23 installments called "Shel Silverstein Visits...". In the process, he created his own style that was amusingly unconventional, yet filled with subtle pathos.