He seems to be a complex figure. We can report from personal observation that the Cowboy has tattoos on each shoulder: Jesus on the left and Satan on the right.
Wikipedia reports that the Naked Cowboy was ruled “not immoral” by conservative talk show host Larry Elder in 2000.
Also, he’s suing Mars candy corporation for dressing a blue M&M in Naked Cowboy non-garb. Key quote:
“All I’ve got is my underwear. It’s the most brilliant thing that’s ever been created from a marketing perspective. You can’t stop it.”
From the Who2 blog:
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