Country star Jake Owen recently shared a remarkable story about the late Jimmy Buffett. He described Buffett’s surprise performance at his annual charity event in Vero Beach, Florida. The “Margaritaville” singer made a memorable entrance that perfectly captured his free-spirited persona.This event happened in 2019. It was a return favor after Owen performed with Buffett at a hurricane relief benefit. According to Rolling Stone, the moment left a lasting impression on Owen and the entire community.
A Legendary Arrival in Flip-Flops
Jimmy Buffett flew his own plane to the Vero Beach airport. He disembarked wearing his signature flip-flops and a Hawaiian shirt. His longtime collaborator, Mac McAnally, accompanied him with a gig bag slung over his shoulder.The pair went straight to the venue and performed an acoustic set for the crowd. After the show, Buffett simply got back on his plane and flew himself out. Owen reflected on the surreal nature of having a legend “stop by for a little bit” in such a casual, iconic way.

Honoring a Musical Legacy
The friendship between the two artists continued until Buffett’s passing in 2023. Owen was later invited to perform at Buffett’s official celebration of life concert at the Hollywood Bowl. This 2024 tribute brought together an incredibly diverse group of music legends.Owen described the experience as uniquely unifying. He noted that only someone like Jimmy Buffett could bring such different people together through music. This event also solidified Owen’s creative partnership with Shooter Jennings, who produced his new album.
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Jake Owen’s recollection provides a heartfelt and personal glimpse into Jimmy Buffett’s genuine character. The story underscores Buffett’s lasting impact on fellow musicians and fans alike. His legacy continues to inspire a spirit of generosity and musical freedom.
Thought you’d like to know-
When did Jimmy Buffett play at Jake Owen’s charity event?
Jimmy Buffett performed at the Jake Owen Foundation fundraiser in 2019. He made a special trip to Vero Beach, Florida, for the acoustic set. This was after Owen had performed with him at a hurricane relief show in 2017.
What was Jimmy Buffett’s signature style at live events?
Buffett was known for his casual, island-inspired attire. He was famously photographed in flip-flops and Hawaiian shirts. This style was consistent from the stage to his personal life, even when flying his own plane.
Who performed at Jimmy Buffett’s celebration of life concert?
The 2024 tribute at the Hollywood Bowl featured a wide array of artists. Jake Owen shared the stage with Paul McCartney, Joe Walsh, and Snoop Dogg, among others. The event highlighted Buffett’s unique ability to unite different musical worlds.
How did Jimmy Buffett’s appearance impact Jake Owen’s career?
The charity performance and subsequent tribute concert deepened Owen’s artistic connections. It helped solidify his working relationship with producer Shooter Jennings. This influence is reflected in Owen’s new album, “Dreams to Dream.”
Why is Jake Owen’s story about Jimmy Buffett significant?
It reveals the authentic and generous nature of the music legend. The anecdote shows Buffett’s willingness to support fellow artists for good causes. It’s a testament to his character beyond the public stage persona.
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