When Zac Brown got to play with his hero Jimmy Buffett on the latter’s hit “A Pirate Looks at Forty,” the vibes were too poignant. As a lifelong fan of Jimmy, you can tell it meant the world for Zac to play with the trop rock icon and sing this timeless song with him. The stripped-back acoustic arrangement was just the perfect way to deliver the collaboration, which was rounded out by Mac McAnally on guitar and vocals. Many fans returned to the duet after Jimmy’s passing to celebrate the great man’s music.
It’s easy to see why fans tuned into this particular song and performance to remember Jimmy, as the simpler arrangement really brings out the emotions of the nostalgic and thoughtful lyrics. Jimmy and Mac’s voices singing in harmony together are so creamy and satisfying. Fans pointed out that they could really hear Jimmy’s influence on how Zac approached the vocals here, and how perfectly their voices blended as a result. The Music Man has to say that at 62 years old, Jimmy is sounding fantastic here!
Jimmy, Mac, and Zac filmed the “A Pirate Looks at Forty” performance on December 9, 2009, in Nashville, Tennessee, for CMT Crossroads. Fans loved the collab and added comments such as “OMG. The three of them singing this song is perfection! Jimmy, Zac, and Mac! Tears are filling my eyes and running down my face!” and “RIP Jimmy. This loss is going to stay with us, but he left us his music to enjoy!”
Zac and Mac have performed Jimmy Buffett’s music on more than one occasion. After Jimmy’s passing, Mac joined country star Kenny Chesney to perform an acoustic duet on “A Pirate Looks at Forty” at the CMA Awards. Zac Brown Band and Alan Jackson then performed “Pirates and Parrots” and “Margaritaville.” You could really hear the emotions on display here, and it looked like Kenny and Alan were getting choked up at points.
Jimmy Buffett released “A Pirate Looks at Forty” as the lead single from his fifth studio album A1A. The song hit number 101 on the US Billboard Bubbling Under Hot 100 chart. The Music Man readers might be interested to hear that despite this very modest chart performance, “A Pirate Looks at Forty” became a fan favorite over the years. The song is currently Jimmy’s fifth-most popular track on Spotify, with 62 million streams. It was also a firm staple of Jimmy’s live sets throughout the years.