Back in 2010, something special happened on CMT Crossroads—a show known for pairing country artists with musicians from other genres. Zac Brown Band and Jimmy Buffett teamed up for an unforgettable performance of “A Pirate Looks at Forty,” blending their styles in a way that felt effortless and natural.
It was the perfect match. Both Buffett and Zac Brown Band have built careers on feel-good music that celebrates the coastal, laid-back lifestyle. Their shared love for storytelling and escapism made this collaboration one for the books.
A Song That Speaks to the Soul
Originally released in 1974 on Buffett’s A-1-A album, “A Pirate Looks at Forty” is more than just a song—it’s an anthem. It tells the story of an aging free spirit reflecting on his past adventures, regrets, and love for the open sea. Over the years, it has become a fan favorite among Parrotheads and remains a staple in Buffett’s live shows.
When Zac Brown and Buffett took the stage together, they honored the song’s original vibe while adding a fresh, heartfelt twist. Zac’s warm, soulful voice blended beautifully with Buffett’s signature easygoing delivery, making it feel like two old friends swapping stories over drinks by the shore.
A Seamless Collaboration
Musically, the performance struck the perfect balance. Zac Brown Band’s rich harmonies and skilled acoustic guitar work meshed effortlessly with Buffett’s signature island-style rhythm. It wasn’t just a duet—it was a celebration of the carefree, ocean-loving spirit that both artists embody.
Zac has long credited Buffett as one of his biggest influences, and you could feel that admiration throughout the performance. The way he sang with both reverence and authenticity made it clear that this was more than just a song to him—it was a tribute to the man who helped shape his own musical journey.
Buffett, always the charismatic performer, embraced the moment with his trademark charm, grinning as he traded verses with Zac. The energy between them was genuine and heartwarming, making the performance even more special.
A Moment That Means Even More Today
Looking back, this CMT Crossroads performance remains one of the show’s most seamless and memorable collaborations. It brought together fans of Buffett’s tropical escapism and Zac Brown Band’s country-rock storytelling, proving that great music knows no boundaries.
With Buffett’s passing in 2023, this duet now carries even more emotional weight. It serves as a beautiful reminder of his timeless influence on country and trop rock—a moment where the torch was passed from one generation of beach-loving musicians to another.
If you haven’t seen this performance, it’s well worth a watch. It’s the kind of music that makes you want to kick back, sip a cold drink, and let your worries drift away with the tide.
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