Under the bright lights of the 57th CMA Awards, Kenny Chesney took the stage—just him, his guitar, and a promise to honor a legend. With every raw, stripped-down note of A Pirate Looks at Forty, he carried the weight of memory, a tribute Jimmy Buffett would have loved. As the final chords faded, the night swelled with Buffett’s greatest hits, each song a wave of nostalgia. Alan Jackson hid behind dark sunglasses, his voice betraying him, while Zac Brown let his tears speak. Jimmy wasn’t just honored—he was felt, missed, and loved. Rest easy, Beach Bum.

 

Kenny Chesney and Mac McAnally singing and playing guitar on stage

Kenny Chesney and Mac McAnally singing and playing guitar on stage

Kenny Chesney Sings “A Pirate Looks at Forty” In Emotional Jimmy Buffett Tribute

The 2023 CMA Awards became a deeply emotional evening when Kenny Chesney and Mac McAnally took the stage to honor the late Jimmy Buffett with a moving performance of “A Pirate Looks at Forty.”

The tribute celebrated Buffett’s enduring legacy and his profound impact on music, culture, and the country genre.

“A Pirate Looks at Forty” is one of Buffett’s most iconic songs, encapsulating his signature style of storytelling, nostalgia, and a longing for simpler, carefree days.

Written in 1974, the song speaks to the reflective musings of a man embracing his identity as a modern-day pirate, living life on his own terms. For fans of Buffett, it is more than just a song—it’s an anthem for dreamers and wanderers.

Chesney, a longtime friend and collaborator of Buffett, took the lead with heartfelt vocals that captured the wistful essence of the track. Mac McAnally, a legendary musician and frequent member of Buffett’s Coral Reefer Band, provided intricate guitar accompaniment and harmony vocals, grounding the performance in authenticity.

The two artists poured their hearts into the song, creating a poignant atmosphere that resonated with the audience.

The stage was adorned with soft lighting reminiscent of a tropical sunset, evoking the laid-back island vibe that defined Buffett’s music.

As Chesney and McAnally sang, images of Buffett were displayed on a screen behind them, bringing the legend’s spirit to life and prompting tears and cheers from fans and fellow artists alike.

This tribute was more than a performance—it was a celebration of Buffett’s life and his influence on countless musicians and fans. Chesney and McAnally’s rendition of “A Pirate Looks at Forty” was a heartfelt farewell to an irreplaceable icon, reminding everyone of the joy, freedom, and storytelling Jimmy Buffett brought to the world.

If you want more music and videos from Kenny Chesney, check out his YouTube Channel. Fans can also connect with him on Instagram and Facebook. Get news, updates, and tour info on his official website.