It was 1985 (or so) and I was 8 (or so) riding with my Bam to somewhere in her brown Caprice Classic. She was smoking a Capri, one of those weird long and ultra-skinny cigarettes. I liked watching her smoke. I know now I shouldn’t have. But the way her thin hands embraced it and her perfect nails complimented it. It just looked ladylike. Feminine. And beautiful. She pushed a cassette into the tape deck and looked at me and said as the tape clicked into place “don’t tell your mother I let you listen to this”. The song was Pencil Thin Mustache. I watched her sing along, tapping the cigaretted hand and nails, keeping in time on the steering wheel. The tendrils of smoke escaping as she mouthed “the Boston Blackie kind”. I didn’t know what I listening to or who Boston Blackie was. I didn’t really understand the song but then He Went to Paris came on and I realized I was sharing a special moment with my Bam. That was my first encounter with Jimmy Buffett.

It was 1992 (or so) and I was 15 (or so) and Makenzie gave me a copy of Fruitcakes. We listened to it on repeat, driving around in her white Toyota truck that she taught me to drive a stick shift in. I went to my first Buffett show with her. We wore coconut bras and made sure our fins to the left and fins to the right were on point. That same year (or so) my mum gave me a copy of the book Where is Joe Merchant as my birthday book. I read it overnight and was consumed by the adventures of Frank Bama. I fell in love with the Caribbean despite having never been there, decided I wanted to become a pilot of either a Grumman Goose or a P-51 Mustang, and knew I would one day travel the world. Buffett once said, “I sell escapism”, and I bought it, hook, line, and sinker.

It was 1997 (or so) and I was 19 (or so) and I was in college, working at a bar called the Loomis. My boss, Ed, was a huge Parrot Head, and every year he organized massive expeditions to Star Lake to see Jimmy in concert. When I say massive, I mean MASSIVE. He rented an RV, brought a generator to run the blender, and wore a grass skirt. The man was all in. We’d spend weeks leading up to it listening to Buffett, planning our trip and what drinks and other items we’d have. We lost Ed a few years ago and though I only went once, it was an experience I will never forget that keeps me connected to him and the light he shared with the world.

It was 2003 (or so) and I was 26 (or so) and I had decided to get married. It’s not something I dwell on or discuss much these days, but despite it being a moment of regret and failure, it is also a moment of unprecedented joy and familial love that I will always remember. I danced my father/daughter dance to Little Miss Magic. To this day when I hear that song I remember the feeling of being a fairy tale princess, beautiful and timeless in my father’s arms. It is that moment and that song that I remember, that helps ease the pain of my embarrassing foray into matrimony. It is a moment, regardless of the outcome, that I treasure and love and come back to every time I hear that song.

I didn’t know Jimmy Buffett; I never met him, shook his hand, spoke to him, or had dinner with him. What I loved about him was personal because of what his words and his music and his ideology meant to me at pivotal moments in my life. I feel this loss deeper than most celebrities because in moments of great happiness, he was there in some way or fashion. Losing Jimmy Buffett meant the end of an era to me. A goodbye to a man and a legend that for 45 years of living played a role in my own thoughts and desires and dreams. I have a particular harbor I hope to retire to and plan to have oysters and beer for dinner soon. I carry my tattered copy of Joe Merchant with me on long trips. And as I grow older, I appreciate a Pirate’s view on 40 more and more each day, I know that my wrinkles represent the places my smile has been, and that I just want to live happily ever after, every now and then.