It is not unusual for Uncle Bob to strip down to his underpants to please a crowd.

Uncle Bob has been a Jimmy Buffett fan since before Buffett was big, when he saw him at a fair in Virginia.

“I got to Key West when I was bent out of shape, going through a divorce. Some friends abducted me and brought me here because I play a lot of Buffett and am a Parrothead. I had no means to get back and have been here 14 years,” Bob deadpannned.

Uncle Bob is a musician and entertainer but he calls himself a “beer cheerleader.”  When he is on stage at Rick’s or Sunset Tiki Bar and Grille, he said there is no greater feeling than inspiring the crowd. He plays Jimmy Buffett, of course, as well as country, classic rock, originals. And then there are his comedic bits — familiar jokes that stoke the crowd.

“Everybody who knows me knows the famous lines ‘Put em’ up, ‘Put em’ up, ‘Put em’ up, ‘Put em’ down. It’s a toast I do,” said Bob. “I also have an original song called ‘Third Beer Down’, which is a song I wrote to encourage cruise-shippers to stay in a bar and have three beers.”

In his years playing Key West, Bob said he’s seen it all. And he’s come up with a few observations, as well.

“Nurses and teachers live in such structured arenas that when they come down to Key West, they go crazy — dancing, singing, drinking. They’re here for the ride of their lives,” said Bob. “When they go back home to the classroom or hospital, they are not the same person.”

Jason Burning, visiting from Central Florida, said Uncle Bob’s performance is the highlight of his trip.

“Uncle Bob is sexy and knows how to treat a crowd. People come in from the street to see what is going on and everybody in the bar is getting loud and having fun,” said Burning.

Bob said the city and community has grown on him throughout the years.

“Most people say they like the weather and water in Key West, what I like is the attitude. I have seen more people pick up garbage bags then throw them down. I picked one up on my way here,” said Bob with a grin. “A quick judge of a person is if they are the thrower-awayers or picker-uppers. I think we should have as little impact on the planet as we can.”

Aside from his years performing in Key West Bob has lived an interesting life. He is a veteran of the Army, owned a pet store and was a professional chef for 25 years. Originally Bob wanted to work as a chef on Little Palm Island but hit a roadblock when he realized he couldn’t walk there.

“I owned a pet store because I have always loved girls that love animals and I still cook in my free time. Anything that is fresh is good,” he said.

Two Great Danes, Truman and Luna Moon, are part of his Key West family as well as his girlfriend Angie Crenshaw whom works at Mel Fisher’s.

Aside from loving his 20-hour workweek and living his dream on stage, he is an active diver.

“Diving is as close as you can come to flying like Superman without having that ability. Sometimes I just lay on the bottom and enjoy the feeling,” said Uncle Bob.

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