Key West Aerial
  • Musical legend Bob Dylan depicts Key West, the free-spirited island at the end of the Florida Keys Overseas Highway, in a lyrical ballad on his new album. (Photo by Rob O'Neal, Florida Keys News Bureau)

     

  • By: Laura Myers
  • July 8, 2020

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 mid-June.

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.

Little White House Key West

Dylan’s Key West ballad mentions island landmarks including Mallory Square, Bayview Park and the Little White House where Harry  Truman spent 175 days during his presidency. (Photo by Andy Newman, Florida Keys News Bureau)

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.”

A sultry-voiced Dylan paints a colorful portrait of the island town. ”Down in the flatlands, way down in Key West/ I got both my feet planted square on the ground/ Got my right hand high with the thumb down/ Such is life, such is happiness/ Hibiscus flowers, they grow everywhere here/ If you wear one, put it behind your ear/ Down in the bottom, way down in Key West,” he sings.

Historian-author Douglas Brinkley, a friend of Dylan’s who has visited the island, describes the song as “a beautiful piece of art … Dylan knows it’s my favorite on the CD.”

Capt. Tony's Saloon Key West

According to Capt. Tony’s owner, Dylan was a “quiet guy” who seemingly enjoyed hanging out at the popular bar.

Dylan’s Key West connection is symbolized by a bar stool with his name painted on it at Capt. Tony’s Saloon, a popular watering hole established more than 60 years ago by colorful former mayor Tony Tarracino.

The saloon has hosted other notables including renegade songwriter and children’s book author Shel Silverstein, playwright Tennessee Williams and literary legend Ernest Hemingway — who were all residents of the island at one time or another.

Joe Faber, who purchased Capt. Tony’s in 1989, recalled that the captain, who died in late 2008, knew Dylan.

“I remember Tony speaking about him,” Faber said. “Dylan was a quiet guy and he would come in here, sit and hang out.”

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.

Others include country superstars Kenny Chesney and Toby Keith, and former resident Jimmy Buffett — whose musical portrayal of the Florida Keys’ lighthearted water’s-edge lifestyle jumpstarted his multidecade career. Buffett and Dylan are acquaintances who have expressed admiration for each other’s work in interviews.

There’s also 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 that is now in its 25th year).

To hear “Key West (Philosopher Pirate)” and other songs from “Rough and Rowdy Ways,” just visit bobdylan.com and follow the links.

 

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