Shel Silverstein was a multi - talented children ’s generator , comic artist , poet , playwright , and songster , and above all else , arule - ledgeman . FromThe Giving TreetoWhere the Sidewalk Ends , his title are beloved by children and adults alike . At the time they were written , though , they defied vulgar notion about what a " children ’s " write up could and should be . This is n’t all that surprising , considering that the Chicago - born source , who passed away in 1999 , lead a somewhat unconventional life . Here are eight thing you might not know about him .

1. One of Shel Silverstein’s first jobs was selling hot dogs in Chicago.

Shel Silverstein did n’t always desire to be a author , or even a cartoonist or songwriter . His first love was baseball . " When I was a kid—12 , 14 , around there — I would much rather have been a good baseball player or a collision with the girls , " he oncesaidin an interview . " But I could n’t wreak orb , I could n’t dance . Luckily , the girl did n’t want me ; not much I could do about that . So I started to draw and to indite . ” The close-fitting he came to his MLB dream was when he landed astintat Chicago ’s Comiskey Park , selling blistering Canis familiaris to White Sox devotee .

2. Shel Silverstein never finished college.

Silverstein was expelled from one school ( the University of Illinois ) and drop out of another ( the School of the Art Institute of Chicago ) . eventually , he managed to get through three years of the English syllabus at Chicago ’s Roosevelt University , but his studies get to an precipitous end when he was draft in 1953 .

3. SHel Silverstein was a Korean War veteran.

In the fifties , Silverstein was drafted into the U.S. armed military service . While he was stationed in Korea and Japan , he also worked as a cartoonist for the military publicationStars and Stripes . It was his first big cartooning gig . " For a guy of my age and with my limited experience to suddenly have to turn out cartoons on a mean solar day - to - daytime deadline deadline , the task was enormous , '' Silverstein toldStars and Stripesin a 1969interview .

4. Shel Silverstein worked forPlayboymagazine and was Part of Hugh Hefner’s inner circle.

That ’s veracious : the lovable tike ’s author was onPlayboy ’s payroll for many years . He begin pull back comics for the workforce ’s magazine publisher in the 1950s and ended up becoming closefriendswith Hugh Hefner . In fact , he often spend weeks or even months at thePlayboy Mansion , where he wrote some of his book . His cartoons for the magazine proved so popular thatPlayboysenthim around the world to find the sense of humor in berth like London , Paris , North Africa , and Moscow during the Cold War . Perhaps his most off - colour grant , though , was visiting a nudist camp in New Jersey . These drawing were pile up in the 2007bookPlayboy ’s Silverstein Around the World , which includes a prolusion from Hefner .

5. Shel Silverstein wrote Johnny Cash’s hit song “A Boy Named Sue.”

Few multitude know that Silverstein was a songwriter , too . One of hisbiggest hitswas the funny tale of a boy who learned how to guard himself after being relentlessly strong-arm for his feminine - sound name , Sue . The song was popularise by Johnny Cash and ended up being his top - sell I , while Silverstein was awarded a Grammy for Best Country Song . you may take in Silverstein strumming the guitar and blackguard the lyrics alongside Cash onThe Johnny Cash Showin the video above . Silverstein also write a follow - up call from the pa ’s head of view , The Father of a Boy Named Sue , but it did n’t take off the room the original did .

6. Shel Silverstein is in the Nashville Songwriters Hall of Fame.

Three geezerhood after his death , Silverstein was inducted posthumously into this undivided society of songwriters . He wrote more than 800 songs throughout his career , some of which werequite raunchy . But hisbest - fuck songswere perform by country caption like Loretta Lynn and Waylon Jennings . “ His compositions were directly identifiable , meet with idealistic wordplay and enchanting , sense of humour - fill tale , ” the Nashville Songwriters Foundationsaidof Silverstein ’s medicine .

7. Shel Silverstein wrote the first children’s book to appear onThe New York Timesbest sellerS list.

A igniter in the Attic(1981 ) was thefirstchildren ’s leger to ever make it onto the prestigiousNew York TimesBest Sellers lean . It remained there for a thumping 182 week , break all of theprevious recordsfor hardcover book at that meter .

8. Shel Silverstein wasn’t a fan of happy endings.

If you could n’t already tell byThe Giving Tree ’s sad conclusion , Silverstein did n’t think in turn over his stories glad close . He felt that doing so would alienate his young reader . " The child asks why I do n’t have this happiness matter you ’re say me about , and comes to opine when his joyfulness stops that he has failed , that it wo n’t make out back , ” the writer said in a 1978interview . This turned out to be a risky move , andThe Giving Treewas turn away several times for being too deplorable or too unconventional . fortuitously , after four year of seek for a publisher , it find a dwelling house at HarperCollins ( then Harper & Row ) and has go on to become one of the intimately - selling — and most beloved — nipper ’s book of all time .

A interpretation of this story run in 2019 ; it has been updated for 2021 .

Ralph Keating via Flickr // CC BY-NC 2.0