Famous Musicians Inspired by The Florida Keys
Bob Dylan loves Key West. In fact, the legendary singer-songwriter immortalizes it as “the enchanted land” and “land of light” in a ballad he released in 2020.
Dylan’s 9:35-minute ode, titled “Key West (Philosopher Pirate),” is featured on “Rough and Rowdy Ways,” the artist’s 39th studio album and his first to be released with original songs in eight years.
The ballad begins with McKinley, who decides to travel down the Florida Keys Overseas Highway to Key West — the continental United States’ southernmost city.
“Stay on the road, follow the highway sign/ Key West is fine and fair/ If you lost your mind, you will find it there/ Key West is on the horizon line,” Dylan sings. “Key West is the place to be/ If you’re looking for immortality.”
With an insider’s knowledge, the 79-year-old Dylan lyricizes Key West landmarks Mallory Square and Bayview Park as well as the island city’s Amelia Street and fabled history: “Truman had his White House there.”
The song is lauded by Rolling Stone Magazine as “a poignant 9-minute accordion noir about an old desperado heading off to Florida to make his last stand, brooding over the end times, with only his radio as a reminder of the life he left behind.”
Dylan, who was awarded the Nobel Prize for Literature in 2016, also wrote a track titled “Florida Key” that was released in 2014 on the album “The New Basement Tapes.” However, he is far from the first high-profile musician to be attracted by the lure of the Keys and Key West.
There’s also county superstar Toby Keith, and singer/writer James Slater, whose “Key West Address” was named the island city’s official song during the 2008 Key West Songwriters Festival (an annual gathering of some 150 top-tier performing songwriters).
Kenny Chesney is another local musical favorite whose book, Heart Life Music, reflects on a Key West visit that became one of his favorite memories with fellow island icon, Jimmy Buffett, whose musical portrayal of the Florida Keys’ lighthearted water’s-edge lifestyle jumpstarted his own multidecade career.
It’s a story that begins with dinner on Duval Street, stumbles into the island’s Christmas parade down Duval Street, and ends in one of the most iconic studios in the Keys: Shrimp Boat Sound.
That night, Jimmy shared stories with Kenny about the people and places that shaped him, from Hemingway and Tennessee Williams to the old sailors, songwriters, and free spirits who defined Key West.
Later that trip, the two recorded together at Shrimp Boat Sound, and that’s where Kenny says he finally saw “a part of Key West through Jimmy’s eyes.”
