Shel Silverstein was more than just a quirky, kid-friendly poet with whom we youthfully chuckled while leafing through Where the Sidewalk Ends or A Light in the Attic. Indeed, as your perfectly sensible dad choked back tears while reading to you about the relentlessly cruel passage of time lovingly explored in The Giving Tree, he might well have been unaware of the epically debauched lifestyle of the bittersweet story’s wild-man author.

No doubt about it, Silverstein was an amazing guy. Case in point: he won two Grammys and was posthumously inducted into the Nashville Songwriter’s Hall of Fame on top of being a celebrated children’s author selling over 20 million book copies and counting.  But he also smoked a metric shit-ton of weed, sang obscenely, engaged in legendary partying (often on a houseboat), wrote a lot of fairly bent plays for grown-ups and obviously spent a lot of time thinking, writing and drawing about smut. In fact, some of our readers might remember that Shel Silverstein spent several years as a cartoonist for Playboy Magazine.  They might also recall that not only did Silverstein pen the lyrics to “A Boy Named Sue,” a tune made famous by Johnny Cash, and for which he won one of his Grammys, but that Uncle Shelby also wrote a sequel to “A Boy Named Sue” in which Sue’s dad turns him into kind of a live-in housekeeper/sex slave. The list goes on and on, really.
 

  
So allow me, as a primer for the uninitiated, or as a walk down a rather raunchy memory lane for those of you already in the know, to take you on a perhaps enlightening, but by no means comprehensive tour of some of the more explicit Shel Silverstein content available on the world wide web.  The stuff that follows is, of course, all pretty chuckle-worthy and, while fairly tame when judged by the standards of other smut, is in no way safe for work. 

Take for example this passage from Silverstein’s long-form poem “The Devil and Billy Markham,” a Faustian ode to the hustler that pits a down-on-his luck Nashville songwriter (Billy) against the Dark Lord himself. After the devil beats Billy in a dice match, he damns him to your standard eternity of painful hell roasting. After a while though, Lucifer realizes that unending damnation isn’t quite as shitty if people don’t get a reminder now and then about how awesome life used to be. So he sends Billy back to earth for 13 hours during which time he is allowed to lecherously fornicate with anything that walks, “man or woman or beast,” and no one will say no.  To sweeten the deal, if anyone does happen to put the kibosh on Billy’s inevitable sexcapade, Billy gets to return to earth.  Of course, all good things come to an end, and the Devil sends Billy a 30 second last call for banging as it were:

And Billy Markham, he stops. . .and he squints at the Devil. . .and says. . .“Sucker. . .I’ll take you.”

“Foul!” cries the Devil. “Foul, no fair! The rules don’t hold for me.”

“You said man or woman or beast,” says Bill, “and I guess you’re all of the three.”

And a roar goes up from the demons of Hell and it shakes the earth across,
 And the imps all squeal and the demons scream, “He’s gonna fuck the boss!”

“Why, you filthy scum,” the Devil snarls, blushing a fiery red,
“I give you a chance to live again and you bust me in front of my friends.”

“Hey, play or pay,” Billy Markham says. “So set me free at last,
 Or raise your tail and hear all Hell wail when I bugger your devilish ass.”

The clippings below come from Playboy Magazine and were created as part of a series in which Silverstein traveled all over the place looking for scenes from the fringes of society. They’re hardly scandalous, but perhaps offer a slightly different take on Silverstein if you’re only familiar with “Falling Up”:
 

 

 
Then there’s this one. Larry Moyer, apparently an old pal of Silverstein’s, reads a lengthy drug fueled epic called “A Perfect High” in which the strung out protagonist pushes the limits of excess.
 

 
Next, here’s some footage of Silverstein himself playing a tune called “Show It at the Beach,” in which he addresses the then recent closure of several nude beaches in Sausalito, California:

Finally, check out this playlist of some of Silverstein’s choicest cuts wherein he covers a range of topics veering from predatory, murderous children and his sexual prowess, to venereal disease, pornography, ludes and a handful of other scintillating topics: 

I could do this all day, but I think you get the idea. My intention was simply to summarize, but if you happen to come across a coarse Silverstein specimen of your own lurking under some digital rock somewhere, by all means, go ahead and post it in the comments in the true spirit of a compendium.