The 2023 CMA Awards became an unforgettable night when Kenny Chesney and Mac McAnally took the stage to honor the late, great Jimmy Buffett with a moving performance of “A Pirate Looks at Forty.” What unfolded was more than just a song — it was a heartfelt farewell to a man who defined an entire way of life.
Originally written in 1974, “A Pirate Looks at Forty” perfectly captures Buffett’s soul — his love for storytelling, nostalgia, and living life by his own rules. Chesney, one of Buffett’s closest friends, poured every ounce of emotion into his performance, while McAnally — Buffett’s longtime bandmate — added his signature touch on guitar and harmony, creating pure magic on stage.
Bathed in soft golden light, the performance felt like a warm evening on a tropical shore. Behind them, photos of Buffett smiled down as the audience swayed, teary-eyed and grateful. For a few minutes, it was as if time stood still — the crowd, the music, and the memory of Jimmy Buffett all blending into one beautiful goodbye.
It wasn’t just a tribute — it was a celebration of a legend who taught the world to slow down, smile, and “live like it’s always five o’clock somewhere.”
