2017-07-13 / Arts and Entertainment News


Jeep Caillouet’s long road to Key West
Florida Weekly Correspondent

“I was born in Arkansas, raised in Tennessee and fell in love with a Cajun Queen in New Orleans,” Jeep Caillouet says, introducing his life’s story. “I had two brothers. My daddy was a construction worker, he worked on the dam. He had 13 deerhounds. My mommy — whipped my ass.”

Listening to the anecdotes and tales of Jeep’s life is the subject of book material. What you believe will be a 20-minute conversation can easily turn into two hours in the blink of an eye.

“I went to school just north of New Orleans. Mom would drive me to school, but as soon as her car was gone, I’d hitchhike to New Orleans. The bus was a dime and a nickel. I’d spend my days on Bourbon Street. Then I’d take the bus as far back as it went and hitchhike my way back to school just as mom came to pick me up.” Did he miss much by not attending? Possibly. “But I can conjugate a verb in 36 tenses.”

Jeep ended up attending Pearl River Junior College in Poplarville, Miss., where he majored in art. He still embraces the creative soul of an artist in the truest sense of the word, from building campsites with waterfalls, to half-car-half-house conch cruisers with custom paint jobs, to a puppet show stage he calls the “jukebox” with special effects such as a sound system and a fog machine.

Jeep, by the way, is not his real name. “I didn’t care for my real name,” he said, so he took the name of the little magical creature from the Popeye cartoons as a stage name. “When I went to Memphis, we were called Jeep and the Jeepsters. We played seven nights a week, and won the Mid-South Battle of the Bands out of 50 bands in five states. One of the prizes was some recording time. In Memphis, you had to be somebody and have followers. You had to know people, like Elvis or the ‘Memphis Mafia.’ A buddy coming up, a harmonica player, introduced me to Dave Banjoseed who said we should go play the streets of New Orleans.”

So, at 7 a.m. the next morning, Jeep hitchhiked to New Orleans and set up on the 700 block of Bourbon Street with his banjo. “I had a cowboy hat back then. My plan was to play a song and then pass my hat. I had left my banjo case open back by the wall, and while I was playing, I noticed that people kept dropping money in the case. So, I slowly started scooting back. I discovered then that, after all the expenses, and dividing the money up between four guys in a band, I could make a lot more money playing alone. I made more money in the first set on the street in New Orleans than I ever did in a bar.”

Then, one day, Jeep thought, “I’ve never been out West.” He packed up everything he owned and $250, “including a Winchester .223 varmint gun wrapped in a blanket that I took on the city bus,” and went as far as he could go, to Houston, where, “I knew a guy, right off the interstate.” He began the life as a nomadic musician, soon heading to Austin.

“I had no direction to go. Nowhere to go. No work. It was hard to get used to.” He ended up in Kerrville Texas, the last town on the edge of the desert, no water and only desert ahead of him for three days, nothing but his banjo, a bedroll and a suitcase. After nearly succumbing to the elements, he was picked up by a trucker. “I said, ‘please can I have some water.’ And the guy said ‘all I have is a Coke’. I had two of them.”

Soon Jeep found himself traveling and busking for 16 years all over the western United States: New Mexico, Boulder, Aspen (where he remained based out of an elaborate campsite that he built over the years), Jackson Hole, Seattle, Portland, Santa Cruz, and more. Each winter he had to break down camp before traveling, due to the 16-foot winter snows and 60 mph winds, then rebuild everything each spring.

“I’d put down a new layer of carpet over the last ones each year. When we left the final time, it was 16 layers thick.”

While living in Aspen, Jeep became a father to daughter Wendi Michelle, now 27 and a manager at a Boca Raton West Marine.

“I ended back in New Orleans, and my friend, Smeglie, told me about Key West, and that you could make a living playing here. I had a Coupe DeVille with a house built on the back — the ‘Jeepillac’ I called it — it won Conch Cruiser of the Month in Mangrove Magazine — and so in 1986, I came down. When I arrived and looked around, I said, ‘you mean I can do this every day?’”

Jeep parked his Jeepillac in the parking lot behind the Bull (no parking attendants back then) and began playing banjo at Foley’s Square (where Rumrunners/ Coyote Ugly/Teasers has since occupied), for two years, while entertaining tourists on Mallory Square as a white-faced clown with his dog, Bucksnort, who collected his money for him.

“I started this routine,” he said, finding a groove that worked for him. “I wanted to wear a T-shirt and shorts every day, but not sweat. So, for the past 22 years, I’d play Mallory Square through the winter, then I’d leave and go on tour, Memphis in the spring, Aspen in the summer, Jackson Hole in the fall, and anywhere in between. I was a full-time tourist.”

Through the years he’s entertained as a white-faced clown, playing his banjo, doing a puppet show from his handmade jukebox and almost always with his beloved dogs, who have always been a part of his act, from collecting tips from his audience and dropping it into his tip bucket, to walking a high wire. He retells their names with a sentimental look in his eye: Bucksnort (the first), Mo (Mo’ Money), Cleo and his newest sidekick, Lottie Mo (Lottie Mo’ Money).

In the meantime, Jeep also mastered the art of sailing, and competes in all the local sailing races, including the annual Wreckers Race out to the reef and back, put on by Schooner Wharf. “I’ve won first place and third place,” he said proudly. “But my race is the Around the Island Race.”

It’s impossible to put the life of someone so colorful and creative as Jeep Caillouet in such a small space. So, I’ll just let him sum up:

“I just decided when I was young that I wanted to play an instrument, and not a guitar because everyone was doing that. So, I rented my first banjo for $10. I had no clue how to play, so I practiced a lot,” he said. “I play out on Mallory Square now but only when I want to. I don’t have to worry about a PA, hauling equipment, or traveling around. I don’t have to please anyone anymore except my audience.”

Catch this colorful Key West icon whenever you can, on Mallory Square at the nightly sunset celebration. ¦

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