“This Was Right When My Life Changed”: Kenny Chesney Recalls Hearing Jimmy Buffett for the First TIme

It's not hard to see the lasting impact the late and legendary Jimmy Buffett has had on Kenny Chesney, with the latter picking up the tiki-bar-baton and helping to keep the spirit of Buffett's sun-soaked, glass-half-full Gulf and Western sound alive and kicking.

Chesney has paid homage to the ‘Come Monday’ hitmaker on a number of occasions, with the Knoxville native performing Buffett's classic, ‘A Pirate Looks at 40’, as part of the emotional 2023 CMA Awards tribute to the latter with Mac McAnally.

During a new conversation with Bobby Bones’ BobbyCast podcast, Chesney recalls the moment he first saw Buffett live, “When I moved to Nashville, I had zero money. I was living with a friend that I was in a bluegrass band with in college off of Belmont. She let me stay in her house because I had nothing. It was right before I signed with Acuff-Rose Music, and a lot of my friends were going to go see Jimmy Buffett at (which is no longer there) a place called Starwood Amphitheater”.

Chesney stresses how moving and show-stopping he found that vibrant, island-inspired concert, “And I went to see Jimmy. It was pouring rain that night. We went in a party bus. I went home that night and I was lying in bed and I was staring at the ceiling going, ‘What did I just see?’ I had been to a lot of concerts, but I never saw somebody love their audience quite like that. And it made an impression”.

Chesney reflects on how poetic and fated it felt when, later on, he crossed paths with Buffett, “That was in the summer of ‘91. Now you fast forward 12 years...when I first met Jimmy Buffett. I was with my friend Holly Gleason and she had a friend in Palm Beach that knew Jimmy, and we were playing in Vegas at the same time”.

He expands, “Jimmy was playing across the street at the MGM and...this was right when my life changed...I was playing the arena at Mandalay Bay. We walked over and there was Jimmy and some of his road family with him at the pool at the Four Seasons in one of those cabanas. I walked up and I went, ‘There's the guy I saw play in the pouring rain in Nashville, never knowing that I would become friends with him and collaborate with him and be in the studio with him and become friends with him and get to know him on any level’”. The duo went on to record an array of duets, including a beautifully reimagined take on Buffett's ‘Trying to Reason with Hurricane Season’ for Chesney's Songs for the Saints album.

Chesney likens this idol-to-friends dynamic to how Megan Moroney is with him today. Moroney grew up with Chesney as one of her favourite artists, and saw him perform in Atlanta while in college, before touring with him in 2024 as part of his Sun Goes Down stadium run. They have since become endearingly close friends, and teamed up for the full-circle, CMA-nominated anthem, ‘You Had To Be There’, last year.

Elsewhere during their chat, Chesney cites the 1985 compilation album, Songs You Know By Heart - in particular ‘A Pirate Looks at 40’ - as one of his most beloved Buffett records, “He was one of the first people that taught me it was possible to paint pictures with words, and it took my brain somewhere else. A kid from East Tennessee that didn't know that it was possible to sit on that boat somewhere, on the bow of that boat. This music really meant a lot to me...[It was] the first time I heard ‘A Pirate Looks at 40’, which is still one of my favorite songs ever....I played ‘A ’Pirate Looks at 40’ [during early shows] because of the story of it, you know...I played that song on a stool with a tip jar in a lot of different places”.

He fondly concludes, “I truly loved the storytelling. I love the simplicity of it...It can take a kid's imagination from East Tennessee anywhere...this was one of the albums that I feel like...built Jimmy's life...and it sure made me curious about what was out there”.

Chesney and some of his fellow artists, such as Zac Brown Band, Mac McAnally and Niko Moon, are all keeping the sunny joie-de-vivre of Buffett's world in focus, with the ‘It's 5 O’Clock Somewhere’ icon's legacy sure to last for decades to come.

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