As we get older in this world, the news increasingly turns sour. No, I’m not talking about wars, pestilence, politics or the many whack jobs running around our world these days. I’m talking about the inevitable loss of the people we all know and love, the folks we grew up with on TV, radio, records and the silver screen.

The Boomers are the first mass culture in history. Unlike our parents, we grew up having the same experiences in common. We often speak in a shorthand of song lyrics and lines from our favorite movies or episodes. We all know who the Fonz is, we can all quote lines from most Beatles songs, many of us had Farrah or Hamill hairdos, we have done the Macarena, and we knew everyone in Mister Roger’s neighborhood.

The heroes of our youth grew older right along with us, and inevitably, one by one, they are passing away. With social media, we often hear about a passing before it’s in any news feed. Within moments, social media pages become a long litany of mini obituaries, filled with memories of the first (or last) time we saw them play, or what our favorite movies of theirs were, or in the case over the weekend, a scrolling panacea of cheeseburgers and margaritas.

I don’t even have to name the person. Chances are good that you are either a Parrothead or know one. You may even be sleeping with one. Whether you liked his music or not, his impact on music is known throughout the industry. Everything Troprock flowed from this one artist. From Paul McCartney and Keith Urban to Kenny Chesney and Caroline Jones, you come to find out that he really was bigger than life; a storyteller and troubadour that comes along perhaps once in a century.

I first heard a Jimmy Buffett song back in the 1980s. Some guy was auditioning to be the new guitarist in the band my brothers and I had. He played Margaritaville. I thought it was a catchy tune. I didn’t know who originally sang it. This was long before iTunes or Alexa, where you can simply ask who did a particular song. To find out, you had to go to a record store, one run by a music savant who could not only tell you the artist, but the album, the session players and who did the cover art.

I slowly became hooked. After I went solo as an entertainer, I started learning many Buffett songs. Not always the popular ones, if you could call any Jimmy Buffett song outside of Margaritaville “popular”, but ones that spoke to me personally.

His life did too. We were both journalism majors. The life of a pious Catholic was not for us. He often said that he wasn’t a great musician or singer, something I had laid claim to long before I heard of him. But he could sure entertain and so could I. We were both born storytellers and could charm a room in moments with a fictional fact or factual fiction. When I became a Seafair Pirate, I longed to live the pirate’s life I heard in his records, “writing checks the morning couldn’t cash” as one of his album liners noted.

Eventually, this love of living a pirate’s life led me to Key West. My first visit was because my then-wife and I won a trip for four to Disneyland in a local ball race. Our ball rolled in first, and we won the trip. Sharon and I traded it in for a trip to Key West instead. It turned out to be my son Parker’s first trip; We smuggled him on the plane in his mom’s tummy. It was the first of his many visits to Key West too, as I ended up moving to Florida for eight years to live as a writer a few feet from the beach. There, I pondered answers to questions that plum evaded me, only to find that my own quest for treasure would lead me back to my home waters in Washington.

Still, I think of Key West as my home away from home. I’ve spent a lot of time there over the years. I can even say I was God’s own drunk on more than one occasion.

I even had a product in the Margaritaville stores for a time. I had contacted Sunshine Smith with the idea, and she bought dozens of my 24-Hour Marriage Kits and sold them through the Key West, New Orleans and Charleston restaurant gift shops.

In 2003, I met Jimmy in Key West. Well, sort of. He was recording License to Chill in his recording studio along the waterfront. My band was playing across the way as part of the Pirates in Paradise Festival. At one point, his bodyguard motioned for us to come over, but the idiot selling capes in the booth between us and the studio door thought Carlton was pointing at him. So our big chance to sing background on a Buffett song never happened.

During a break, I went over by the studio, just in case someone famous came out. I was looking at the Sebago catamaran, fondly recalling the time I almost drowned jumping off the side of her when I heard a very colorful conversation coming from some guy to the left of me. Every other word was an expletive. I didn’t want him to know I was listening, so I did the old, look everywhere else before glancing over at the colorful conversationalist.

To my surprise, it was Jimmy Buffett. He was obviously not happy about something as he continued to lambast the person on the other end of the line. He looked over at me, dressed as a pirate, and I looked at him. We gave each other the courtesy nod peers give to one another, acknowledging that each one of us, at that moment, wished to have the other’s life.

I’m often asked why I didn’t get a photo with him. I mean, he might have loved getting a photo of him with a pirate. But me? I don’t do that. He has a job, just like I do. I was doing mine, and he was doing his. We were both pirates, sailing the course we were meant to sail. There was no need to capture the moment. It was perfect just the way it was.

I guess his bodyguard felt bad about the mixed signals moment. He let us know that we should be at Margaritaville that night. He couldn’t say why, but he said it would be worth it. That night, we got an impromptu concert at the restaurant. Jimmy at his best with some of the Coral Reefers, and Carlton, his bodyguard, to the left of the stage, smiling at us.

So perhaps when I was informed of Jimmy’s passing that my reaction was somewhat tempered. We’re all going to go away someday. Some just get more press than others. We are all here for a frightfully short time, and as we get older, the days left get shorter and the moments we have become more precious.

It does seem fitting, though, that when word came that Jimmy had died, I was doing the same thing I had been doing when I first met him in Key West some 20 years ago, living a pirate’s life. I thought back to the moment we had met as I threw on my pirate gear, slung my guitar over my shoulder and headed down to the docks to bring joy into the lives of others. For me, the day was a way to honor one of my heroes of my own youth. I may be growing older, but definitely not up. I’ve lived a pirate’s life for some 40 years now, and I’ll continue to defy gravity until I make my own final trip around the sun.

Somewhere north of the Emerald City, with my heart in Margaritaville,

–          Robb