Shel Silverstein on WTTW: America’s Favorite Uncle, America’s Favorite Dirty Uncle

Archival video from the golden era of WTTW’s Soundstage captures the author, cartoonist, singer-songwriter, and Wrigley hot dog vendor in the two sides of his persona, and their appeal to two very different age groups.

When I was a child, I loved Where the Sidewalk Ends. When I was a man… well, I didn’t put away Where the Sidewalk Ends, but I did learn to enjoy Shel Silverstein hits like “Don’t Fall Asleep on the Road” (sadly not online) and the gentlemanly-country-sounding “Quaaludes Again” (no, seriously). A post by Sarah Weinman, which captures Silverstein in his hometown, playing the on-and-off-again WTTW show Soundstage, reminded me of how singularly weird the career of Wrigley Field’s greatest hot dog vendor was. One song is about a nude beach in Sausalito; the other you’ve probably sung to your kids:

Then, in the second clip, Shel’s sitting on a regular chair surrounded by children. Loud, quiet, all races and creeds and genders, and most of them are pretty damn enraptured by the bald man with the salt and pepper beard. And why not? He’s singing about being eaten by a boa constrictor and of a girl who simply would not take the garbage out and of the unicorn that was supposed to hitch a ride on Noah’s Ark. It is, simply, a magical clip. Like, if I were a kid, I’d want this man to come over to my house and read me books and be the bestsest uncle ever.

[snip]

So yes, two clips. One he’s the bestest uncle ever and the other, he’s talking about his member. Nobody bats an eye. I love this so, so much.

Usually artists appeal to the generations by being generically unobjectionable; Silverstein was able to keep two artistic careers running simultaneously, one wonderfully childish, one wonderfully adult (don’t introduce your kids to The Great Conch Train Robbery until they’re out of college, maybe later).

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