Childhood & Early Years
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.
The situation became worse when his sister was born in 1934. With another mouth to feed, Nathan remained tensed and irritated the few hours he was at home. Shel now began to bury himself in comic books. With his mother, he also listened to the radio broadcasts a lot.
In 1935, as Nathan’s financial situation improved considerably, he moved his family out of his mother-in-law’s home into their own place at 2853 W. Palmer Street. In the same year, Shel began his formal education at Charles R. Darwin Elementary School, moving to Roosevelt High School, in 1944.
Shel was not at all studious, preferring to doodle, both at home and at school. While his father despised this, he was encouraged in his artistic pursuit by mother, resulting in a conflict between his parents. To avoid such bickering, he immersed himself more into drawing.
From his early childhood, Shel also grew a fondness for country music; often listening to Earnest Tubb on the Grand Ole Opry radio show. Playing ukulele, reading books and watching White Sox games were some of his other favorite occupations.
In the fall of 1948, Shel Silverstein entered the University of Illinois, studying there till June 1949, after which he was expelled from the college, possibly because of maladjustment. Next, he entered Chicago Academy of Fine Arts, where too he did not fit in.
Working alone, he had by then developed his own style. Ideas came to him fully developed and he steadfastly refused teachers’ help. Therefore, he had to leave within one year.
In 1950, after leaving the Art School, Silverstein entered Roosevelt University to study English. It was during this period that he had his initial works, both cartoons and writings, published in a student newspaper called Roosevelt Torch. He also helped to lay out the paper.
While studying at Roosevelt University, Shel Silverstein was influenced by his English teacher, Robert Cosbey, who on recognizing Shel’s talent, tried to develop it. But, Silverstein could not finish his course here, as he was drafted in the United States Army in 1953.
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Emergence As Cartoonist
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.
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Singer, Songwriter, Playwright & Poet
In late 1950s, while working for Playboy, Silverstein started exploring other areas of creativity like writing poems and songs. He also started singing, cutting his debut LP, ‘Hairy Jazz’ with The Red Onions in 1959. Although at this stage, his vocal style was still developing, he did make a mark.
Also in 1959, he began his long relationship with the stage, participating in an off Broadway chaotic comedy play called, ‘Look, Charlie: A Short History of the Pratfall’. From then onwards, he wrote more than a hundred one-act plays,
In 1960, he had his second collection of cartoons entitled, ‘Now Here's My Plan: A Book of Futilities’ published. By that time, he had also started illustrating books, among which the most significant was John Sack's ‘Report from Practically Nowhere’ (1959).
In 1961, he had his fourth book, ‘Uncle Shelby's ABZ Book’, released by Simon & Schuster. Although based on one of his Playboy features, it was his first book that contained original material for adults. This was also the year when he cut his second disc, ‘Inside Folk Songs’.
Encourage by Ursula Nordstrom, editor of Harper and Row, he tried his hand at children’s literature publishing ‘Uncle Shelby's Story of Lafcadio: The Lion Who Shot Back’ (1963). Concurrently, he continued to pursue his musical interest, cutting his third album. ‘'Shel Silverstein's Stag Party', in the same year.
In 1964, he had four more books published, nanely, 'A Giraffe and a Half', 'The Giving Tree', 'Who Wants a Cheap Rhinoceros?' and 'Uncle Shelby's Zoo: Don't Bump the Glump! and Other Fantasies’,. Among the four, ‘The Giving Tree’ became his best known work.
In 1965, he published his eleventh book, ‘More Playboy's Teevee Jeebies’; but thereafter he seemed to have concentrated more on song writing, producing seven albums until 1973. ‘The Unicorn’, made very popular by The Irish Rovers in 1968, was one of his greatest hit of this period.
Some other popular numbers composed by him were ‘A Boy Named Sue’, ‘One's on the Way’, Boa Constrictor’ and ‘So Good to So Bad’. While many notable artists and groups had performed his songs, his collaboration with the band Dr. Hook was most successful.
Shel Silverstein also composed original music for several films, such as ‘Ned Kelly; (1970) ‘Who is Harry Kellerman and Why is He Saying Those Terrible Things About Me?’ (1971). In these projects, he showed his versatility by playing several instruments.
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While concentrating on writing music, he must have also continued on writing poetries. One of his major works, ‘Where the Sidewalk Ends’, was published in 1974, after a gap of nine years. Thereafter, he continued to write both poetries and songs, making his mark in every sphere.
His 1981 collection of children’s poems, ‘A Light in the Attic’, broke all records, remaining on the New York Times list for 182 weeks. ‘Falling Up’, published in 1996 was another best-seller, dominating the best selling lists for months.
In the musical field, Silverstein had copyright over 800 songs, many of which remained at the top of the chart for months. He also appeared on radios, having a popular following on Dr. Demento's radio show.
’A Giving Tree’, published in 1964, is Silverstein’s first major work and the best known title. The book, which talks about the relationship between a boy and a tree, has been translated in various languages. As late as 2013, it ranked third on a Goodreads list of "Best Children's Books."
’Where the Sidewalk Ends’, published in 1974, is a collection of poems, dealing in many common childhood concerns. In a poll, organized in 2007 by National Education Association, the book was included in the list of "Teachers Top 100 Books for Children." Its audio edition was released in 1983.
As a songwriter, he is remembered for his many unique creations including numbers like ‘The Unicorn’, ‘A Boy Named Sue’, 'In the Hills of Shiloh', ‘Put Another Log on the Fire’, ‘One's on the Way’, ‘Hey Loretta’, ‘I’m Checkin’ Out’, and ‘25 Minutes to Go’ etc.
Personal Life & Legacy
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.
According his biographer, Lisa Rogak, Silverstein valued creativity above everything else. If he found anything uncreative, be it a place or a relationship, he would immediately walk out of it. He never lived in one place, having apartments, cottages and houseboats in different places.
Silverstein died of heart attack either on May 9 or on May 10, 1999, in his home in Key West, Florida. His body was found by his housekeepers on May 10 and he might have died the day before. He is buried in Westlawn Cemetery in Norridge, Illinois.
In 2002, he was posthumously inducted into the Nashville Songwriters Hall of Fame and in 2014, into the Chicago Literary Hall of Fame.