Key West (Bob Dylan song)

A bar stool with Bob Dylan's name painted on it in Captain Tony's Saloon

An article in Keys Weekly remarked upon how the song appeared to be written with an "insider's knowledge" of Key West, Florida, as the lyrics reference "landmarks Mallory Square and Bayview Park as well as the island city's Amelia Street and storied history: 'Truman had his (winter) White House there.'" The article also quotes Joe Faber, the owner of Captain Tony's Saloon, who said that Dylan used to "come in here, sit and hang out” when the venue was owned by the city's "colorful former mayor" Tony Tarracino. As a result, the bar contains a stool with Dylan's name painted on it.[8]

Historian Douglas Brinkley confirmed that Dylan, who was "very good friends" with Key West resident and fellow songwriter Shel Silverstein, has frequented Key West "off and on throughout his life".[9] Dylan has also expressed enthusiasm for the songwriting of Jimmy Buffett, one of Key West's most famous residents, covering "A Pirate Looks at Forty" in concert[10] and citing the songs "Death of an Unpopular Poet" and "He Went to Paris" as his favorite Buffett compositions in an interview.[11] It is possible that Buffett is the "Jimmy" referred to in the "Key West" lyric, "Like Louis and Jimmy and Buddy and all the rest."

"Key West" is actually the second song Dylan has written about the Florida Keys. He wrote the lyrics to the first, "Florida Key", in 1967, although the words were not set to music and recorded until the song was completed by Taylor Goldsmith for The New Basement Tapes project in 2014. Both "Florida Key" and "Key West" contain a verbal play on "key", using the word to connote both the name of a geographical place as well as a device for unlocking something (e.g., "Nothing's locked, never will be"[12] in the earlier song and "Key West is the gateway key to innocence and purity"[13] in the later one).

Rolling Stone ranked "Key West" the second best song of 2020 (behind only Cardi B and Megan Thee Stallion's WAP)[14] and placed it seventh on a list of "The 25 Best Bob Dylan Songs of the 21st Century".[15] In an article accompanying the latter list, music journalist Rob Sheffied extrapolated from the impressionistic lyrics a narrative about "a grizzled outlaw, hiding out in Florida, hounded by his memories".[16] Hyperallergic's Lucas Fagen wrote that, "in a voice drunk on blood and sunshine, Dylan sings a rapturous, almost operatic ode to the island, going overboard in his praise" but notes that the song "resonates thanks to the specificity and absurdity of its conceit" and calls it "emotionally direct and weirdly moving".[17]

Authors Adam Selzer and Michael Glover Smith have drawn thematic parallels between "Key West" and Harold Arlen and Yip Harburg's "Over the Rainbow"[18] and Dylan's own "Murder Most Foul", respectively. Smith also praised Donnie Herron's accordion playing on the track, which he cites as "the aural personification of a gentle Florida breeze, warmly embodying the 'healing virtues of the wind' that Dylan so memorably sings about."[19] Historian Douglas Brinkley, who conducted the only interview with Dylan to coincide with the release of Rough and Rowdy Ways, described the song as "a beautiful piece of art", adding that "Dylan knows it's my favorite on the CD".[20]

The song's opening words, "McKinley hollered, McKinley squalled", refer to the opening of Charlie Poole's 1926 song "White House Blues", which describes the assassination of President William McKinley.[21] It is ambiguous as to whether Dylan means for the narrator of "Key West" to be listening to the song "White House Blues" or the actual assassination of McKinley via a magical radio. Dylan may have been aware that the first wireless radio transmission was sent across the Atlantic Ocean in 1901, the same year as McKinley's assassination.[22] McKinley also had a specific connection to Key West: His signature foreign policy achievement as President was victory in the Spanish–American War. When the United States became involved in that conflict, Key West was the embarkation point for U.S. troops (under the command of General William Rufus Shafter).[23]

In the second verse, the song's narrator identifies himself with a trio of famous Beat Generation writers: Allen Ginsberg, Gregory Corso and Jack Kerouac. It is likely not a coincidence that Ginsberg, who was close friends with Dylan, once wrote a poem titled "Walking at Night in Key West".[24]

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