Shel Silverstein, recording artist

Shel Silverstein is best known for his fanciful children's poetry, so perhaps you were unaware of his very, ahem, adult side. Silverstein was Playboy's "cartoon-capturing foreign correspondent" as well as a prolific songwriter and burgeoning novelist, reports the Atlantic:

Sticking only to the school-age side of the road means ignoring his prodigious work as a songwriter (Johnny Cash's "A Boy Named Sue"? Dr. Hook and the Medicine Show's "The Cover of the Rolling Stone"? The Irish Rovers' "Unicorn"? The Oscar-nominated "I'm Checking Out" from Postcards From the Edge? All penned by Shel), his one-act plays for Off-Off Broadway venues (which attracted the attention, and later friendship, of David Mamet) and a tentative foray into crime fiction that, if not for his premature passing, might have blossomed into something greater.

Then there's Silverstein's album, Freakin' At the Freakers Ball.  A number of songs that didn't make the cut showcase a risque and raunchy side of Shel:

But Freakers Ball was likely the compromise point on a series of songs Shel recorded a couple of years before the final album was released, songs with eye-popping titles like "Fuck 'Em", "I Am Not a Fag" and "I Love My Right Hand." Some of these songs are available on YouTube. Others may wish to seek the bootleg.