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Tim Istock column: Mamas, don’t let your babies grow up to be naked cowboys 

By Tim Istock
For the Clemmons Courier

So I recently stumbled across an article about The Naked Cowboy, a man who since 1998 has occupied a daily spot in New York City’s Times Square, clad only in a cowboy hat, boots, a pair of white skivvies, and a guitar slung over his shoulder. Oh, and now, given the pandemic, I should add that he also sports a face mask.

OK, so what, right? I’m sure most of you at one time or another, either by virtue of having traveled to New York City and personally witnessed this cheeky crooner doing his thing, or, as a result of having being exposed to him (or is it the other way around?) via a print, internet, or television story, know full well who I’m talking about.

Well, the “so what” is that I’ve got some questions about this revealing personality stuck in my craw, and they go something like this:

  • So what was his early childhood like? Did he display an innate predisposition for performing in front of total strangers wearing only a smile, a trait that would soon find him standing out in front of his house wearing only a pull up and strumming a ukulele?

“Oh Henry, look, it’s the Wilson child out playing his ukulele again in his diaper, isn’t that cute?”

“ Cute? He’s been out there every day for the past six months, I think there’s another word I would use instead of cute, and it rhymes with beard.”

  • And how about elementary school, what did he say when it came time for him to answer the seminal childhood question regarding future career choices?

“OK Johnny, your turn.”

“Miss Grayson, when I grow up, I want to stand out in the middle of the most populous city in the world and perform country songs in my underwear. “Oh . . I see Johnny, yes, well, I think we’re going to move your parent-teacher conference up to this afternoon.”

  • Once his career path was finalized, what did his parents say when the subject of kids and their careers came up during social get-togethers?

“Yes, Henry has finished his PhD in chemistry and taken a job with Dow Corning, while Robert is chief pulmonologist at the Mayo Clinic. How about Johnny, what is he up to these days?”

“Johnny is singing country songs in his BVDs in Times square. We’ve always known he had a lot of raw talent.”

  • He is married now, (to The Naked Cowgirl — I kid you not) but in his single days, did he ever place personal ads or participate in online dating sites, and if so, what was his bio like?

SWM, 40 YO, 6’2”, 210 lbs, blond hair, blue eyes, self-employed as country singer standing smack dab in the heart of Times Square twanging away in my tighty-whities.

There are other questions, of course, like how The Naked Cowboy could somehow manage to become one of the biggest tourist attractions in a city brimming with all manner of iconic entertainment, architectural, and historical sites.

“Boris, forget about the Metropolitan Museum of Art, if we hurry we can catch The Naked Cowboy before he finishes for the day.”

Or, how any couple in their right minds — and that may be the crux of the issue on this one — would willingly pay $499 to be married by the Naked Cowboy in Times Square. He is, after all, also an ordained minister and apparently marries dozens of couples a year.

“Hey, Mom, Dad . . Jamie and I just found these old pictures of your wedding day, who is the cowboy with the butt-huggers on?” Oops.

In the final analysis, as is often the case, the answer to the essential question of why the Naked Cowboy does what he does and continues to do it comes down to one thing, moolah, and apparently plenty of it, as one estimate I read stated that his annual income from undulating in his undies through the Big Apple can reach $150,000! Yup, there are six figures there folks.

Hmmm, $150,000… Let’s see, I’ve got boots and a hat … check … underwear … check .. now, what did I do with that old guitar of mine?