Poet Biographies

The Whimsical World of Shel Silverstein

Shel Silverstein was a prolific writer, poet, and illustrator best known for his beloved children’s works. His whimsical, humorous, and often poignant writing captured the hearts of readers.

Shel Silverstein Portrait Art

Shel Silverstein is best known as an author of poetry and works for young readers. However, he explored many creative avenues, writing books, becoming an actor, writing screenplays, writing music for successful artists, and cartoonist. His best-selling volumes include The Giving Tree and A Light in the Attic. 

Silverstein started off as an illustrator before having a stint working at PlayboyRemarkably he then turned to writing and publishing children’s books and poetry. He was known for his very unique style, which combined fantastic illustration, powered by his unique imagination, with a bold brand of humorBefore his death in 1999, he had established himself as a songwriter, composer, musician, and author for readers of all ages.

Life Facts

  • Shel Silverstein was born in September of 1930 in Chicago, Illinois.
  • His first piece aimed at a young audience was ‘Uncle Shelby’s Story of Lafcadio: The Lion Who Shot Back.’
  • ‘Silverstein Around the World’ was a collection of his illustrated travels around the world.
  • Silverstein wrote the score for films such as ‘Who Is Harry Kellerman’ and ‘Why Is He Saying Those Terrible Things About Me?’
  • He died in 1999 at 68 years old after a heart attack.

Interesting Facts

  • By the age of seven, Silverstein had developed a passion for drawing.
  • He was drafted into the army and served in Korea and Japan.
  • Silverstein worked for Playboy magazine as a cartoonist. 
  • The Giving Tree‘ is thought to be one of the most well-loved and discussed books for children of all time.
  • He had a passion for music and won a Grammy for “A Boy Named Sue”.

Famous Poems

  • ‘Where the Sidewalk Ends describes the differences between the way that an adult sees the world and how a child sees it. The end of the sidewalk represents different things. The child moves beyond the rigid “real world” and into one with “peppermint wind” and one-of-a-kind, unbeatable happiness.
  • ‘Sick’  is a lighthearted and humorous poem that describes a child’s attempts to get out of going to school. She comes up with many reasons why she couldn’t possibly leave the house. Finally, with a characteristic twist, it is revealed that it was Saturday all along.
  • Listen to the Mustn’ts is an uplifting poem that uses nonsense words like “MUSTN”TS” to describe those who tell you that you can’t do something. They are the naysayers who want nothing more than to tear you down. You shouldn’t, the speaker says, listen to them. One should remain open-minded and determined.
  • ‘Dirty Face‘ is a funny piece that contains all the reasons a child’s face is so dirty. He goes through fantasies and adventures, laying out outlandish answers to his parent’s inquiries. This is yet another poem that expresses the imaginative qualities of a child’s mind versus that of an adult.
  • Snowball’ tells the story of a young child who makes a snowball on a wonderful snow day. He takes it into his house and is devastated to wake up and find out that it’s gone. The child thinks that it’s run away and does not realize his wet pajamas are a result of its melting.

Explore more Shel Silverstein poems.

Early Life

Shel Silverstein was born in September of 1930 in Chicago, Illinois. By the age of seven, he had developed a passion for drawing. As a young man, he attended Roosevelt High School, where Silverstein’s cartoons were published in the Roosevelt Torch, the student newspaper. He went on to the University of Illinois and later the Chicago Academy of Fine Arts. It was during his time at the Chicago Academy that he was drafted into the army. He served in Korea and Japan in the 1950s.

Illustration Career

When Silverstein was in the army, he worked for Pacific Stars and Stripes, a publication in which his own drawings were later included. Pacific Stars and Stripes went on to publish his first book. The volume was titled, Take Ten. It included all the cartoons published up until that point.

After leaving the military, Silverstein returned to Chicago, where he submitted cartoons to magazines. He also worked selling hot dogs at ballparks. During this time period, his work was featured in Sports Illustrated and This Week. A year later, Take Ten was reprinted as Grab Your Socks! 

His reputation continued to grow until he became a leading cartoonist for Playboy. He traveled around the world in order to illustrate an expanding travel journal for the magazine. These installments were called “Shel Silverstein Visits…” Some of the locations he illustrated were in England, Spain, and Africa. The journals were collected in the volume Silverstein Around the World.

Writing Career and Relationships

While at Playboy, Silverstein explored other areas of creativity. He began to write poetry and songs. A few poems were contributed to the magazine over the years, including, ‘The Winner.’ He also wrote the volume Playboy’s Teevee Jeebies and followed it with a sequel. It was around this period that Silverstein recorded his first of over twenty albums. It was titled Hairy Jazz and was released in 1959.

In 1960 Silverstein published his next collection of cartoons titled, Here’s My Plan: A Book of Futilities. It featured what was then his best-known cartoon on the cover. The cover depicts two men, prisoners, who are chained to the wall. He continued to work for Playboy throughout the 60s and into the 1970s. His features in the publication were eventually combined into Uncle Shelby’s ABZ Book. It was published in 1961 and was his first book of material aimed exclusively at an adult audience.

It was in 1963 that Silverstein came into contact with a book editor, Ursula Nordstrom, who sent him on the path of writing only for children. His first piece aimed at a young audience was Uncle Shelby’s Story of Lafcadio: The Lion Who Shot Back. It was published in the same year. The following year he published two books, A Giraffe and a Half and The Giving Tree, the latter his most popular. The Giving Tree is thought to be one of the most well-loved and discussed books for children of all time. The main story deals with growing up, happiness, sadness, and sacrifice.

Shel Silverstein diversified into many disciplines, including screenwriting. In 1988 and 1991, he worked on the screenplays for Things Change and Oh, Hell, respectively, alongside playwright David Mamet.

At first, Silverstein had trouble getting a publishing company to pick up the manuscript due to its ambiguous intent after its publication though it became massively popular and has been translated into over thirty languages.

Music Career

By the mid-70s, Silverstein had turned his attention back to music. Silverstein started to operate within musical circles, writing a number of songs recorded by other artists, such as “A Boy Named Sue,” performed by Johnny Cash (for which he won a Grammy), “Sylvia’s Mother,”  and “The Cover of the Rolling Stone,” recorded by Dr. Hook & The Medicine Show, and “Unicorn Song,” performed by the Irish Rovers.

Silverstein also released full-length albums. These included his biggest hit, Freakin’ at the Freaker’s Ball, which spoke on the hippie movement of the 60s. His musical talent spread into soundtracks as well. He wrote the score for films such as Ned KellyWho Is Harry Kellerman and Why Is He Saying Those Terrible Things About Me? as well as many others.

Later Life and Death

The 80s were a less productive period for the writer who had solidified his poetry career in the 70s with Where the Sidewalk Ends. He set this collection to cassette and LP phonograph in 1984 and won the Grammy for Best Recording for Children. One of his most memorable books, A Light in the Attic, was released in 81. It was followed by The Missing Piece Meets the Big O. 

Before his death in 1999, he published Falling Up and Draw a Skinny Elephant. He suffered a heart attack at his home in Key West, Florida, in May of 1999; he was 68 years old. Silverstein was buried in Westlawn Cemetery in Norridge, Illinois.

Influence from other Poets

Shel Silverstein was notably influenced by teachers and editors in his life as well as poets such as Alan Alexander Milne and Lewis Carroll.


What is the most famous Shel Silverstein poem?

By far the most critically acclaimed of his poems, Shel Silverstein’s ‘The Giving Tree’ is part of his best-selling work of the same name. The 1964 poetry book has had many give their own interpretation of the poem’s meaning. Some people believe that the poem is about environmentalism, whilst others see it in a more biblical way, referring to it as a religious parable.

What is the story behind The Giving Tree?

The story of Shel Siverstein’s ‘The Giving Tree‘ centers around the relationship between a tree and a young boy who visits the tree every day to play with it and take apples from its branches. The surface message of the poem reminds us that a consistent pattern of selfishness, without giving back to others, can lead to consequences down the line, thus making the reader consider their own level of altruism or giving back.

What was Shel Silverstein’s childhood like?

Shel Silverstein was born in September of 1930 in Chicago, Illinois, into a Jewish family. By the age of seven, he had developed a passion for drawing. However, Shel was known to have claimed that his father was not as approving of his ‘doodling’ at he would have liked. His drawing helped him through his younger years. As a young man, he attended Roosevelt High School, where Silverstein’s cartoons were published in the Roosevelt Torch, the student newspaper. He went on to the University of Illinois and later the Chicago Academy of Fine Arts.

What is Shel Silverstein most famous for?

By far, Shel Silverstein is most famous for his self-illustrated poetry and prose. However, he was a man of many talents, diving into multiple creative pursuits and succeeding considerably. Some of these areas of interest were songwriting, music, acting, playwriting, and more.

How old was Shel Silverstein when he died?

Unfortunately, Shel Silverstein died at the age of 68 on 10th May 1999 in Key West, Florida. He died from a heart attack at his home.

William Green Poetry Expert
Will created Poem Analysis back in 2015 and has a team of the best poetry experts helping him analyze poems from the past and present. Although he has a background in Automotive Engineering, having worked for McLaren testing supercars, Will has a keen eye for poetry and literature.

4 thoughts on “The Whimsical World of Shel Silverstein”

  1. This Has been a helpful source, like my uncle used to say, “A poem is like a chicken, It has feathers, but it cant fly, so you have to through it off a roof to see if its instincts will kick in, if they don’t, you have a dead chicken on your hands.” Hope He finally got a chicken to fly, after 200 didn’t.


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