Best Of 2023 - RIP To Jimmy Buffett From A 30 Year Parrothead

I woke up to very sad news this morning.   One of my idols passed away.   The great Jimmy Buffett.    Now people who know me know I’m not the most emotional human of all time.  Animals get to me, but that’s pretty much it.  Well here I was at 6:30am this morning literally bawling my eyes out when I heard the news.  It’s kind of crazy that a guy I barely knew could mean that much to me but he did.   It honestly feels like a member of my family died or even a part of me.

I’ve been a Jimmy Buffett fan for going on 30 years now.    I went to my first concert Labor Day weekend when I was 16 years old at the Tweeter Center in Mansfield and I was hooked ever since.  The Labor Day show became an annual event for me marking the changing of seasons in New England from summer to fall.   I consumed everything Jimmy.  I read all his books.  I went to his broadway play.  I went to Key West to see the bars and places he sang about.    I’d say I’ve probably been to 40/50 shows since that 1st show with the last one being last year at the Hard Rock Casino in Ft Lauderdale where honestly I couldn’t help but look around at notice the age of the crowd.   All us Parrotheads were slowly growing old together.    

And I think that’s the thing that makes his passing so emotional for me.   Anytime you are a hardcore fan of somebody for 30 plus years he becomes more than just an artist for you.   Jimmy and his music started marking the passing of time for me.  Certain milestones in my life reminded me of certain songs.   And as Jimmy got older he started singing about getting older.    It all resonated with me. Happy. Sad. All of it.

But it wasn’t just the music.  Another huge reason he meant so much to me is that I’ve always vacillated in my life between whether I wanted to chase money and work my ass off or whether I should just fuck off and disappear somewhere.  I debated this question as recently as last month when I had the opportunity to leave Barstool with a ton of money and already accomplishing more than I ever dreamed of.  Like at what point is it time to slow down and just enjoy life.  Whenever I thought about these questions I’d turn on Jimmy’s music to zone out and think about it.  I had Incommunicado on repeat.  But in the end I decided I wasn't ready to put the book on the shelf.  His music just resonated with me and always has.  

Now I know for those Jimmy novices you may be asking what does his beach bum lifestyle have to do with business or Barstool?     Well despite his laid back persona he’s also one of the best businessmen of our generation.   In fact when I first sold Barstool to Chernin Group they asked me who my business inspiration was.  I had never been asked that question before but I answered without hesitation that it was Jimmy Buffett.   He was nothing short of a genius in the way he was able to take his brand of storytelling and escapism and build an entire lifestyle brand out of it.   Books, bars, casinos, restaurants, alcohol, merch etc.    You name it he did.  He built a fanbase and a culture and stayed true to it and monetized it.  Exactly what we did with Barstool Sports and I always saw the parallels.

Barstool has given me way more perks and opportunity than I could have ever dreamed when I started this company.  There is none higher on my list than getting to meet Jimmy.   He was supposed to play a charity concert during Covid that I was going to host.  The concert never happened but I did a zoom call with him for an hour before it was cancelled. 

We shot the shit about everything under the sun including how when he heard I hated Roger Goodell he knew he’d like me.   I thought that would be the only time I’d get to speak to him but then 2 summers ago he randomly reached out to me and invited me to lunch at his house in Sag Harbor.   When I knocked on the door a girl answered and said “Hi I’m Jimmy's daughter Delaney”  Umm yes I know who you are.  Delaney Talks to Statues is one of my underrated favorite songs.  It was surreal.   I couldn’t believe I was there.   Jimmy spent 2 hours telling stories that felt like he was writing songs as he went along.   There was no real reason for the lunch.  We weren’t planning anything.   Nothing came from it.  I think he just liked meeting people he perceived as interesting and he could potentially work with down the road.   I didn’t ask for a photo because I didn’t want to seem like a fanboy.  I regret that now, but it is what it is.  I did get the chance to meet him a few more times between then and now.   

They say never meet your idols but that didn’t apply to Jimmy.   He was exactly how I pictured him.   Lost in songs and beaches and stories while also zoning in on potential business opportunities.   I definitely feel a bit older and sadder today than I did yesterday.   It's heartbreaking to think we'll never be able to see him perform live again, but the beauty of Jimmy is that his persona and songs will always be shining like a lighthouse in the night for Parrotheads like me.

RIP Jimmy.