Most everyone with ties to Key West has some sort of Jimmy Buffett story. My JB experience began in June of 1985 at the Timberwolf Amphitheatre at Kings Island Amusement Park near Cincinnati, Ohio. I don’t remember the setlist, but it was a great show, and despite the fact the 10,000 seat venue wasn’t even close to capacity, it was fantastic, and I was hooked. Interestingly enough, it is said that the word ‘Parrothead’ was born that night by then-Coral Reefer Band member Timothy B. Schmidt, and it stuck. For the next 35 years, Buffett’s popularity skyrocketed, and he would move on to and completely pack Cincinnati’s 20,000 capacity Riverbend Music Center, often for multiple nights, a total of 54 times. Each year, prior to my Ohio departure in 1996, my friends, and often my very cool parents, would tailgate with the best of ’em. No, we didn’t do grass skirts or crazy headgear, but we did cook cheeseburgers in the parking lot and drink a shitload of beer…It was a rite of summer in Ohio.

After arriving in Key West in 1996, I was obsessed with getting shots of the man when and wherever I could. Word was, he could pop up anytime, anywhere, you just had to be ready…and lucky. Serendipitously, after a year or two, I met JL Jamison who happened to be Jimmy’s right-hand man and studio manager. Over the many years, while never a guarantee, JL got me close to this titan of music whenever it was possible. In 1999, after being hired to shoot the annual Parrotheads in Paradise convention, I was blessed with 25 years of magical photo moments that I cherish to this day. By far, the most memorable of these were the several times Jimmy played on Duval Street during the convention, or his appearances at the Casa Marina Resort. The annual gathering was always filled with great live music, but when the “Buffett Buzz” was in the air, it took on a whole different feel.

In 2005, I created a coffee table book titled Key West Photo Safari, and of course, included a couple photos of Jimmy. No Key West book would be complete without a photo of Jimmy Buffett. Eventually, I endeavored on a personal quest to get a photo with every celebrity who visited the island holding a copy of my book. But my timing was never right with Jimmy. I tried for 18 years. One of my first opportunities presented itself after being invited into Shrimp Boat Sound studio in 2008. I hadn’t gotten permission to shoot, but there I was, literally shoulder-to-shoulder with Jimmy Buffett, camera in hand, heart pounding, and patiently waiting. After about 30 minutes, and a shuffling around of personnel, I looked over and saw him sitting on the arm of the couch, where, by chance, my book was under his “backside.” Realizing this was probably the closest I’d ever get to my book being photogrpahed with Jimmy, I cranked up the ISO, shut off the flash, and grabbed the shot. I figured, well, at least he touched the book. That was the only photo I made that day and I have to now wonder if JL will be pissed, now that he knows that I shot an unsanctioned photo…hope not.

For years afterwards, I would bring a copy of my book to his shows along with the print of him sitting on it, hoping for a moment, but that moment never came.

Fast forward to 2023. We were all thrilled to hear about his Key West shows and while we heard he was having some health issues for a while, the four Key West shows were fantastic, particularly the first of two at the Key West Theater. It was an honor to be in the room that night. Looking around the audience, I got a little choked up, realizing how many uber-cool people I had met during my 27-year JB photo quest. One by one, I kept meeting all these cool people that worked in the Margaritaville Store, many had done so for decades. As I told these Margaritaville alumni numerous times, I thought I had already met all the cool people in Key West, then I ran into this truly “Insane Clown Posse” called the Margaritians. Then there were all the cool people involved with the Parrotheads in Paradise Meeting of the Minds convention. One thing is certain, everyone in Jimmy’s orbit loves a good time.

I would have happily chased Mr. Buffett around with my cameras for another 27 years, but those days are behind us now. Nonetheless, I am deeply grateful for all the killer music, photo ops and lifelong friends that fell into my lap on this crazy little island. Thank you, Jimmy, for a real good time.