Shel Silverstein's Secret, Raunchy Recording Sessions

More than a decade after his death of a heart attack at age 68, Shel Silverstein's career avoids any defining label. Millions of children have anointed him to beloved status thanks to poetry books like Where The Sidewalk Ends and A Light in the Attic, and a visit to the website run in tandem by Shel's estate and his longtime publisher, HarperCollins, might convince you that his work for kids is his primary legacy.

Doing so, however, neglects the full spectrum of what made Silverstein tick as an artist. It rubs out the more than 40 years he spent in the bosom of Hugh Hefner's Playboy empire, a veritable court jester at Mansion gatherings when not traveling the world as the magazine's cartoon-capturing foreign correspondent (see Shel Silverstein Around the World, a coffee table-style compendium of reports from places like Moscow, Spain, and Fire Island) or producing epic poems like "The Perfect High" or "Hamlet As Told on the Street".

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.

But the most remarkable element of his non-children's-lit career was Silverstein's nine albums worth of songs he recorded—and especially the album's worth of unreleased material that might even surprise fans of Shel's adult side.

As a recording artist, Silverstein brought a raspy vocal style (not unlike Tom Waits's satanic older cousin) that came from his teenage years as a Comiskey Park hot dog vendor. And his firsthand knowledge of various scenes (Greenwich Village Beats, the Chicago folk music world, Nashville's Music Row) led to a varying array of song styles and production values. By the late 1960s, this songwriting acumen helped Silverstein move into rock circles, thanks in large part to the New Jersey-based Dr. Hook & The Medicine Show.

Dr. Hook also backed Shel on his most commercially successful album, Freakin' At the Freakers Ball. "Commercially successful" is a relative term for a group of raucous and risque songs like Masochistic Baby." Shel sweetly intones that ever since his baby left him, "I've got nothing to hit but the wall." Dr. Hook gave it as much oomph as its own, Rolling Stone-cover-worthy album Sloppy Seconds, adding a sense of gleeful disconnect to the whole musical affair. The album cracked Billboard's Top 200 and recording label CBS provided a marketing budget, something beyond Shel's resources at the time. The one-sheet ad featured Shel, clad in a jean jacket, patterned shirt and cowboy boats, and what can only be described as a piratical beard, trumpeted as some sort of heir apparent to Gilbert O'Sullivan (!)

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 songsare available on YouTube. Others may wish to seek the bootleg.

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Sarah Weinman writes about books and publishing for the Wall Street Journal, The Daily, and the Los Angeles Times, among other places.

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