Shel Silverstein was actually a Playboy columnist for over 40 years


"And now, children, your Uncle Shelby is going to tell you a story about a very strange lion -- in fact, the strangest lion I have ever met ..." - Shel Silverstein

By Eric Sandler

I can still recall the sing-song verses of "A Giraffe And A Half" from memory without having read the book in over ten years. Moreover, you'd be hard-pressed to find anyone who can discuss the iconic poet, author, illustrator, and singer-songwriter Shel Silverstein without warmly recalling childhood memories of works like "The Giving Tree," or "A Light In The Attic."

There has been so much written about him and far more by him -- but yet, in all likelihood, you probably don't know the full scope of his work. Let's start with this fun fact: Shel Silverstein was a columnist and cartoonist for Playboy Magazinefor over 40 years beginning after he joined the staff in 1956.

The story goes that though Shel hit it off with Playboy's notorious founder Hugh Hefner -- who also happened to be a cartoonist -- nothing happened fast. Hefner was maneuvering an uncertain future for his newly minted magazine while Silverstein was attempting to make a living doing something he was uncomfortable with at the time -- freelancing.

"I really thought I was meeting a guy who [had] just woken up, which is a legitimate concern," Silverstein humorously mused upon observing Hef's silk-pajama garb. But once Playboy commissioned its first few cartoons from Shel and paid good money for them, he was hooked. In fact, those first Playboy checks gave him the grounds to move out from under his parent's roof when they were all too keen to see him fail in his unconventional career and get a "normal" job.

"Normal" wouldn't cut it for Shel though. His career began to flourish in Playboy with travelogues detailing risqué assignments in places like Fire Island [see the cartoons here], Tokyo, and cities around the world where Shel and his photographer would put together joint cartoon-photo features that shed light on worldly locales through the wholly original lens of Silverstein's imagination.

"The cartoons lampoon and deflate the expectations of the tourist, humanising the apparently foreign, yet for comic effect they ring new changes on those same foreign and cultural stereotypes," the blog StreetLaughter surmised.

And so it went, on-and-off, for more than forty years of incredibly underrated material. Oh yeah, and then there are the drug-fueled songs penned and performed by Silverstein as well. But those are for another story ...

Happy Birthday Shel!

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