A Brief interview with the Naked Cowboy

Me and the naked cowboy

Me and the naked cowboy

They say never meet your heroes. You’ll just be disappointed. They’ll be too arrogant or rude or just plain ignore you. Fortunately for me that hasn’t been the case. Whether it was meeting Robin Williams or Neil deGrasse Tyson or now the Naked Cowboy I’ve always found them to be far more kind, gracious and generous than I could have ever imagined. I’d been experiencing a lot of rejection lately so it was with some trepidation that I approached the Naked Cowboy on the streets of Times Square to request an interview. I was expecting him to say no, or “I don’t do interviews.” or “You have to talk to my manager.” or “It’ll cost you.” So I was pleasantly surprised when he said yes. Had I known he’d be so willing to talk perhaps I would have prepared more, but I came equipped only with the questions that had been swimming around in my mind for years.

I found him to be more intelligent, thoughtful and interesting than you might think he would be. I’d always sort of admired the Naked Cowboy. I’d seen him out there on the streets of Times Square for years. Before any of the costumed characters there was the Naked Cowboy. Before the people dressed up as Elmos, Batman, Minions, Spider-Man, Iron Man, the Hulk. Before the topless painted ladies and the CD hucksters. Before the M&M store and all these huge chains he was there.

Despite his name the “Naked Cowboy” he always seemed very wholesome, very family friendly. You never see him harassing anyone for tips or going up to people trying to get them to take a photo with him. He just stands there wearing nothing but a cowboy hat, boots, underwear, a guitar and a smile. You see these other characters going up to people trying to coerce them to take a picture with them. If some kid wants to take a photo with Elmo all these other characters nearby jump into the shot too. And they all want money. They pressure the parents to give them money and if they think it’s not enough they point at their tip bag and want more, more, more.

I’ve never seen the Naked Cowboy do that. If someone wants a picture with him he’s happy to oblige. And afterwards he doesn’t ask for any money. He just goes back to strumming his guitar with a smile on his face and a song in his heart, happy to have made someone’s experience in New York that much more interesting. He doesn’t even have a tip jar or a tip sign or a big bag that says “TIPS” like many of these characters. If someone does give him money he just discretely tucks it away in the hole of his guitar.

I was talking with my friend Dan one day in Times Square and he said “I overheard some tourists looking at the Naked Cowboy and they said “You don’t see that everyday” and I thought “Yes I do.” And I just thought it was the saddest thing ever. I’m so over it. Just shoot me.” And I said “He is a cowboy maybe he’s got a gun.”

But I’ve never gotten tired of seeing the Naked Cowboy. He’s out there to show people something they don’t see everyday. To make their lives more interesting and unusual. He came up with the idea for the Naked Cowboy. He didn’t just go and get some costume of some already known character and dress up as it. He created it out of his own imagination and a slight suggestion of a photographer.

One day , a few years ago I was in Times Square and I saw a family, a mom, dad and three little kids, all younger than teenagers. The dad was trying to take a selfie of himself and the family with the Naked Cowboy, but he couldn’t get them all in. What’s the point if it’s just your faces? Plus the kids were too small to also fit in the frame. I saw the Naked Cowboy looking around trying to get some one to take the photo to no avail so I stepped in. I counted down from three and took a few photos and I was about to hand the phone back to the dad when the Naked Cowboy turned around to show his brief clad butt to take another photo. He did this in such a way as if to suggest that no photo with the Naked Cowboy is complete without a butt shot. Of course he has the words Naked Cowboy painted on the backside of his white briefs (That’s just good brand promotion. Gotta give him credit for that.). I’ve seen him do this several times with people while taking a photo and you often see women playfully grab his butt. So I said “Someone grab a cheek!” And the mom playfully grabbed his right butt cheek. And I said “Someone grab the other one! We need both cheeks grabbed!” And the dad playfully tried to get his little daughter to do it, but she didn’t want to so the dad grabbed the cheek himself. I took a few photos with the mom and dad each grabbing a cheek with the kids there too. They seemed like fun parents. And the kids seemed to be having fun too. As I handed the phone back to the dad I said “There’s next year’s Christmas card.” And some guy nearby heard me and thought it was funny and said to his friend “He said there’s next year’s Christmas card!”

That made my day.

That’s what the Naked Cowboy is about, spreading joy and happiness. Helping people make memories. Hopefully that family will have a fun memory from that time they encountered that cowboy in his underwear in Times Square.

But it’s not just that. There’s something very disciplined about the Naked Cowboy. He’s maintained a muscular physique all these years. And he’s not just out there on warm sunny days, he’s also out there in the bitter cold and snow as well. I remember some days I’d be in Times Square all bundled up and shivering and I’d see him out there in just his underwear and I’d think “How does he do it?” He doesn’t call out sick. He can’t say “I’m working from home today.” Then he’d just be some guy sitting at home in his underwear wearing boots and a cowboy hat.

Earlier I mentioned the CD hucksters in Times Square. They are like the complete opposite of the Naked Cowboy. They go up to people and act like they’re giving someone a free CD and then as the person says thanks and walks off they hassle them and say “Hey that ain’t free! That ain’t free! Gimme money for that!” Or they give people false compliments and offer a handshake all in the purpose of trying to sell a CD that maybe doesn’t even have any music on it. Some of them say stuff like “Hey don’t be afraid of a black person! Don’t be afraid of a black person!” One time I told them I didn’t want a CD and they told me I looked like a homosexual. And I said “What about me looks like a homosexual? I’m wearing a white t-shirt and jeans.” And he said “I’m just sayin’ you look like a homosexual. That’s all!” And I said “Yeah, but you said it like it was an insult.” And he said “I’m allowed to say you look like a homosexual! You can’t say I said nothin’ wrong!” You also see and hear performers in groups in Times Square with these super loud sound systems and they shout and yell and get people to watch them perform tricks.

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The Naked Cowboy doesn’t do any of that. He has no sound system, just a simple acoustic guitar and his own un-amplified voice. He doesn’t approach people saying “Hey want a photo with the Naked Cowboy?” They approach him. He seems to embody this sort of American grit, discipline, and hard work. He didn’t know if this would work out. He set out to do his own thing. He did it his way and found success on his own terms. I was surprised to learn he also sells oysters and wine. He performs in various venues in New York and around the country. He has a real hustle and drive to succeed that’s very admirable. And he does it in a kind, friendly, honest way.

I really enjoyed my brief conversation with him and left with a greater appreciation and admiration for him than I ever had before. He was kind, friendly, energetic and inspirational. As I rode the subway back to my apartment. I realized I had even more questions. How did he go from being the Naked Cowboy to selling oysters and wine? What other books have inspired him? How does he train the other Naked Cowboys? Do they have to maintain an impressive physique like himself? Do they need to adhere to a certain moral code so as not to sully the Naked Cowboy name? Where did he meet all those belly dancers?!

But a part of me likes not knowing. I sort of like that he remains sort of a mystery. An enigma clad in a pair of briefs topped by a cowboy hat. The more I thought about him I felt he sort of embodies a William Saroyan’s preface to his play, The Time Of Your Life. I want to end with those words because I feel they sort of describe how the Naked Cowboy lives his life.

“In the time of your life, live so that in that good time there shall be no ugliness or death for yourself or for any life your life touches. Seek goodness everywhere, and when it is found, bring it out of it’s hiding place and let it be free and unashamed.

Place in matter and in flesh the least of the values, for these are the things that hold death and must pass away. Discover in all things that which shines and is beyond corruption. Encourage virtue in whatever heart it may have been driven into secrecy and sorrow by the shame and terror of the world. Ignore the obvious, for it is unworthy of the clear eye and the kindly heart.

Be the inferior of no man, or of any man be superior. Remember that every man is a variation of yourself. No man’s guilt is not is not yours, nor is any man’s innocence a thing apart. Despise evil and ungodliness, but not men of ungodliness or evil. These understand. Have no shame in being kindly and gentle but if the time comes in the time of your life to kill, kill and have no regret.

In the time of your life, live - so that in that wondrous time you shall not add to the misery and sorrow of the world, but shall smile to the infinite delight and mystery of it.”

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