Jimmy Buffett would have turned 79 this Christmas. Throughout his career, the chief Parrothead earned a reputation for flashy entrances. Jake Owen remembers one vividly: Buffett, in flip-flops and Hawaiian shirt, piloting his own plane to Vero Beach, Florida, to give a special performance at Owen’s annual charity concert in the country singer’s hometown.
After Owen performed at a 2017 Hurricanes Irma and Maria benefit show with Buffett in Tallahassee, Florida, Buffett returned the favor in 2019 and played an acoustic set at the Jake Owen Foundation’s annual fundraiser.
“He literally flew his own plane in, landed at Vero Beach airport, got off in flip-fops and a shirt with Mac McAnally, gig bag on his shoulder, and played for the people of Vero Beach,” Owen tells Rolling Stone’s Nashville Now podcast. “And then he got back on his airplane and flew himself out of there. Talk about that story, right? ‘Jimmy Buffett’s gonna stop by for a little bit in his airplane and play some songs…’ To have that kind of memory is amazing.”
When Buffett died in 2023, Owen was tapped to sing at the “Margaritaville” legend’s celebration of life concert at the Hollywood Bowl in L.A. the following year. Owen says it’s where he and Shooter Jennings, who produced Owen’s new album of traditional country, Dreams to Dream, really bonded. “He’s such a huge Jimmy Buffett fan,” Owen says of Jennings.
He also recalls the surreal moments he spent onstage in the closing all-star jam. “I was singing into a microphone looking face to face at Joe Walsh, singing ‘Let It Be,’ while McCartney played piano, and Snoop Dogg’s smoking a blunt,” Owen says. “Only Jimmy Buffett could bring these people together and provide this type of unity… and understanding that music is freedom.”
Owen released Dreams to Dream earlier this month and joined Nashville Now for an emotional interview about what led to the album, a creative and personal left turn for the Nashville hitmaker behind radio juggernauts like “Barefoot Blue Jean Night.”
Download and subscribe to Rolling Stone’s weekly country-music podcast, Nashville Now, hosted by senior music editor Joseph Hudak, on Apple Podcasts or Spotify (or wherever you get your podcasts). New episodes drop every Wednesday and feature interviews with artists and personalities like Lainey Wilson, Hardy, Charley Crockett, Kings of Leon, Gavin Adcock, Amanda Shires, Shooter Jennings, Margo Price, Ink, Halestorm, Dusty Slay, Lukas Nelson, Ashley Monroe, Old Crow Medicine Show’s Ketch Secor, and Clever.
