"Key West is fine and fair. If you lost your mind you'll find it there..."  AKA "Philosopher Pirate"
Channel: Artur Artist presents The Casper Collection
Date: 2022-02-21

Bob Dylan's fine rendition of "Key West (Philosopher Pirate)" filmed at New York's Beacon Theatre, November 21, 2021.  (Note: The first two-thirds of the video is quite good but the last third has some technical problems.  Still better than nothing, I hope.)

From Dylan's acclaimed 2020 album 'Rough and Rowdy Ways,' "Key West" is a tough song to characterize.  As the subtitle suggests, it is indeed a rambling philosophical meditation - one that incorporates confessional elements, bits of fragmentary storytelling, a little travelogue, and some seemingly random stray facts ("Truman had is White House there") reminiscent of Dylan's Theme Time Radio Hour shows.

 "I'm searching for love and inspiration, on that pirate radio station." 
This single, opening line of the second verse, one could argue, neatly sums up Dylan's entire life and career. 

Meanwhile, the main feeling that seems to run throughout the song, uniting all the disparate pieces with each and with the lingering, haunting tune, is an overwhelming sense of wistfulness. 
 Key West isn't some unattainable paradise in the song, but it's clearly much more than a mere geographical location.  

In his musings, I think Dylan does reveal some truths about who he feels he is:  
   I was born on the wrong side of the railroad track
   Like Ginsberg, Corso and Kerouac
   Like Louie and Jimmy and Buddy and all of the rest

-- He's always felt like an outsider

    I got both my feet planted square on the ground
    Got my right hand high with the thumb down

-- Although he may be a visionary, he isn't a dreamer;
   and he has that Gemini mind which always sees both sides and ever vacillates between them

     I’ve never lived in the land of Oz
     Or wasted my time with an unworthy cause

-- Another assertion that he's reality-based.  He fights for what he believes in, but he's no starry-eyed romantic who goes "tilting at windmills."

Altogether, "Key West" is a song that adds up to so very much more than the mere sum of its parts.  It's a wistful world away from wherever you happen to be, one that you can get lost in every time you listen to it again.