I have been asked how did you get the Chart Room. So let me share this story with my many Trop Rock fans. We were listening to the ladies of Trop Rock show at Surley Siren Saloon and when it was over a good Parrothead friend Debbie Hess invited us to join them at The Chart Room and something happened that I will never forget and share with you here:

This story is the biggest highlight of my short career as a Trop Rock musician!

For those unaware The Chart Room is where Jimmy Buffett played his first bar gig in Key West. It is located in the Pier House Hotel at 1 Duval St. and is everything you would expect of an old nostalgic Key West Dive Bar, including Free Popcorn, Peanuts and Hotdogs. It is a must see for Jimmy Buffett fans and is ground zero for Trop Rock Musicians. Jimmy played for Heineken and tips, more to come on that.

Oct 30th 2025, I had played a few songwriter rounds earlier that day around town for Trop Rock’N Duval and had my guitar with me. I set it against the wall upon entering the Chart Room As the bar was small and very full when we arrived. We enjoyed the evening mingling with parrot heads and meeting new friends, as the bar was emptying out at the end of the evening, my wife Kim said “you should play your song, Almost Jimmy.” Now, They don’t have live music at the Chart Room and haven’t for a long time. They also had house music being piped into the room from their stereo. I did not want to play over the house music, so I said, “No I’m not gonna try to play over this music.” Well, earlier in the evening we met a Key West Icon and our new driver Steven, he heard Kim ask me to play and heard me say No I can’t play over the house music, and Steve said “wait, let’s do It. I wanna hear this song” Steve turned to the bartender, Joko and said, “can you turn the house music off so Crash can play his song, Almost Jimmy!” Now, earlier in the evening Steve told us that they don’t do live music in The Chart Room, and the last person to play in there was Jimmy, which I find hard to believe since it was back in 1971, but that is what I was told. So I’m looking at Joko and thinking there is no way this is gonna happen right now. Joko looked at me and said, “You wrote a song, let’s go, Let’s hear it,” and he went in the back to turn off the music. As I’m opening my guitar case I’m imagining Jimmy sitting down and playing this bar so many years before and thought, man this is really happening. I poured everything I had into playing my song in that moment for 4 people, my Wife, Steve, our bartender Jocko, and the whole time I was singing I imagined Jimmy was there with me (so he was the 4th). I finished the song to their thunderous applause and realized I just did what Jimmy did so long before and was completely overcome with emotion. Steve said we need to get him back to play here again! Joko asked “if we were in town long?” I told him “we leave Sunday. “ He said, “what are you doing Saturday?” My eyes got big and I said “If you are asking if I will play here the answer is absolutely, YES, Whatever you want me to do on Saturday I’ll be here.” Joko said, “I can’t pay you.” I immediately told him “I don’t need paid, I would play here the same way Jimmy did, for Heineken and tips.” We all laughed, and settled on 6pm Saturday, and instantly Joko became my next favorite Key West bartender. Our new friend and driver this week, Steve drove us home that night and I was on Cloud Nine trying to wrap my head around what just happened. I booked my first gig in Key West by myself and it was The Chart Room of all places and they never have live music! I barely slept that night. WHAT A WAY TO END AN AMAZING DAY!

THE CHART ROOM, NOV 1st 2025

I walked through the door to a packed house. Joko and Steve were cheering “he’s here!” Word had gotten out and people were hanging out as they heard there was live music. The table was full but everyone scooted around and made room and gave me a chair. “Oh wow, are you playing music here tonight?” “Live music at The Chart Room, that’s awesome.” The gig started very impromptu I looked up at Joko, smiled and gave him the thumbs up and he turned off the music. I had no sound system or speaker, so there were no announcements. I just pulled out my guitar and sat down by the window under the Capt Tony pic and started playing Buffett tunes, as it should be. I Buffett songs to start, Tin Cup Chalice, He Went to Paris, Havana Day Dreaming, Margaritaville, Son of a Son of a Sailor, 5 O’Clock somewhere, Southern Cross, Come Monday, & of course My fav – Pirate Looks at 40. People were singing along enjoying the music as it should be. I was so happy with the vibe inside and it was starting to get even more crowded. The place was not full of Trop Rockers so I got some requests for other songs outside of Buffett’s library, which actually helped me because while I know a lot of Buffett songs I was running out. People were singing along and it was just a really fun night for all types to enjoy. I was getting ready for a break and like clockwork, around 7:15-7:30 Boomer and Jerry Diaz showed up and they brought a Trop Rock crowd from fresh off the sunset cruise. The inside crowd started to change from a mix of people to almost all Parrotheads and it was time to get back to Buffett music. I was also honored that Boomer Blake, Jerry Diaz, Reggie Starrett, Ricky Lamb, Donnie Howard all attended and I had just got done playing for an hour and a half. So it was cool to step back and watch the people I have looked up to and respected for years play. Everyone took turns and it was an awesome night of people singing and dancing. The guys would play 3-5 songs and pass the guitar. I’m pretty sure I heard Tin Cup Chalice 5 times that night, and I sang it every time. It started to die down as I believe people wanted to head down Duval, so I put the guitar away for a bit. I think the Coconut Telegraph was hard at work on Duval cause people started to come in again. It was down to Donnie Howard and I, so we broke the guitar back out and played every buffet song we knew till around 11:30. Donnie is a machine with the guitar, just hammering out all the Buffett hits and some deep tracks. It was an Epic night! Joko was so happy. Steve live streamed almost the whole concert. As the night was winding down Donnie left so I sat on a stool and I played all my originals to the crowd that was still there. I even played my new song, 3 Streets which isn’t quite finished yet but talks about Duval St. as the hour got later, It was almost the same people left in the bar from the Thursday before when I got the gig. I just kinda sat there at the end of the night, reflecting and feeling the most fulfillment I have ever had at the end of a gig. Thinking to myself, I just started something in Trop Rock community that could be very big. I saw the emotion in the other musicians as they played, it was awesome. It was exactly what I felt the Thursday before when I played my song in there. The history alone is overwhelming. I was the last person to walk out as Joko was cleaning up. We high five’d and hugged it was like, Damn we just did that. He thanked me and we talked for a bit about how much fun it was. I mean I played The Chart Room and had the time of my life. I shared the night with Trop Rock Legends. I thought to myself I got my start at the place where Jimmy got his start. We left, stood outside talking for a little while. and took a few more pictures and celebrated down Duval till about 3 in the morning. I figured what the heck I was done, I had no gigs left and we flew home on Sunday. It was time to Celebrate! I had done everything I wanted to do on this trip and so much more. I was so proud of myself, I sang my songs, told my stories, met so many amazing people and musicians, I played at Hogs Breath, Hanks Hair of the Dog, Surly Siren Saloon, Viva Argentinian Steakhouse, Kaya Island Eats, The Backyard Bar, and The Chart Room…. I mean what could top playing at The Chart Room?

WELL STAY TUNED BECAUSE I GOT ONE MORE SURPRISE GIG TO GO……