Key West (Philosopher Pirate)

Album: Rough And Rowdy Ways (2020)


  • This is an accordion-heavy song about an unnamed character who has fled to Key West, Florida, to live out his days in anonymity. He never gives a reason for his flight, but there's a sense in the song that he's some kind of outlaw or, at least, an outcast.

    It's natural to assume that it's Dylan speaking as himself (or some fantasy version of himself), but throughout his career he's assumed first person roles of other characters in his songs. There are also many indications in "Key West" that he's not speaking about himself, with the clearest probably being:

    Twelve years old, they put me in a suit
    Forced me to marry a prostitute
    There were gold fringes on her wedding dress
    That's my story, but not where it ends
    She's still cute, and we're still friends

    To the best of our knowledge, Dylan has never been forced to marry a prostitute.
  • Key West is an island off the southern tip of Florida where Jimmy Buffett set up shop. Dylan, with roots in Minnesota and New York, isn't known for soaking up the sun in the tropics.
  • On that pirate radio station
    Coming out of Luxembourg and Budapest

    This is one of the strangest lyrics in the song. Luxemborg is a country in Western Europe that borders Germany, France, and Belgium. Budapest is the capital of Hungary, which is also a European nation. Both are around 5,000 miles from Key West (straight-line distance) and why their pirate radio stations would be playing in Key West is a mystery.

    Interestingly, there is a Key West radio station named Pirate Radio Key West. They couldn't verify Dylan was talking about them in the song but report being the only "pirate radio" they know of associated with Key West, so it's a fair shot Dylan picked it up there, even if maybe he does end up using it in his typically elliptical manner.
  • I was born on the wrong side of the railroad track
    Like Ginsberg, Corso and Kerouac

    Allen Ginsberg, Gregory Corso, and Jack Kerouac were all figures of the 1950s Beat Generation, which was a cultural phenomenon (many refer to it as a "movement," but it lacked the conscious direction or organizational drive requisite for that title) that heavily influenced the 1960s counterculture in general and Bob Dylan in specific. It was characterized primarily by its literature, but it spilled out into the popular consciousness as well with its focus on a wandering Zen master lifestyle and resistance to traditional American values.

    Ginsberg and Dylan were friends. Dylan also wrote a blurb for Ginsberg's book of collected poetry. There's footage of them visiting Kerouac's grave. Ginsberg was one of the most celebrated poets of his time. His poem Howl was revolutionary in form and content. It was taken to court for obscenity and, following a trial in 1957, became a landmark in American free speech. The courts decided that it did, indeed, have social merit, despite its graphic sexual imagery.

    Kerouac is the most prominent member of that generation. His novel On the Road is one of the most impactful books in American literature, with a style of conversational, rolling prose and a celebration of rootlessness and even lawlessness that hadn't been seen at the time in popular American letters.

    Corso is an interesting addition to the list because his work never achieved the prominence of Ginsberg's poetry or Kerouac's prose. He had a poem in 1958 titled Bomb about the atomic bomb that created a lot of controversy and conversation at the time, though it hasn't been nearly as remembered as Kerouac's novels or Ginsberg's poem Howl.

    In the book Dylan in America, Dylan recounts getting to New York at the tail end of the Beats' era. In discussing names, he specifically mentions Ginsberg, Kerouac, and Corso (as well as poet Lawrence Ferlinghetti).
  • More lyric analysis:

    Like Louis and Jimmy and Buddy and all the rest

    "Buddy" instantly brings to mind rock pioneer Buddy Holly, writer of staple tunes such as "Peggy Sue." This suggests the whole line is talking about musicians (as the preceding line was talking about writers), which places the "Jimmy" as Jimmy Buffet, who is the musician most associated with Key West. His signature song "Mararitaville," in fact, was written about Key West. The "Louis" is vague, but it's tempting to say it's jazz legend Louis Armstrong simply because he was such an influential musician and one who blazed his own unique and revolutionary artistic trail.

    On Newton Street, Bayview Park

    Newton Street and Bayview Park are both real places in Key West. Newton is five blocks northwest of the park.

    I played Gumbo Limbo spirituals

    Gumbo Limbo is a name for the turpentine tree (scientific name Bursera simaruba). The term appears all over Florida. There's a Gumbo Limbo trail in the Everglades and a Gumbo Limbo Environmental Complex in Key West.

    Mystery Street off of Mallory Square
    Truman had his White House there

    Mallory Square is on the western tip of the island of Key West. President Harry Truman kept a winter house near that spot. It was called the "Harry S Truman Little White House."

    McKinley hollered, McKinley squalled
    Doctor said, "McKinley, death is on the wall
    Say it to me, if you got something to confess"

    The McKinley name most immediately brings to mind William McKinley, 25th President of the United States, who held the position from January 11, 1892, to January 13, 1896. Nothing else in the song indicates that this is who being referenced, though, so it's pretty ambiguous.
  • The song's wistful yearning for a tropical island escape is reminiscent of Dylan's song "Goin' To Acapulco."
  • Though 9:34 long, "Key West (Philosopher Pirate)" is still only the second-longest song on the Rough and Rowdy album; "Murder Most Foul" clocks in at 16:54.

Comments: 10

  • AnonymousMcKinley reference is unlikely to be the 25th President as he was shot some years before anyone could hear about it on a radio as they weren't in use in 1901 when McKinley was assassinated. Also, '12 years old they put me ina suit, forced me to marry a prostitute' is an oblique reference to his barmitzvah
  • Nicholas J BullockMcKinley is probably Larry McKinley. Louis could be Louis Jordan as well. Buddy could be Buddy Bolden and Jimmy is probably Jimmy Dorsey all from New Orleans.
  • Barry Mccollom from Plano, TxJust a few insights I have picked up while reading about "Key West(Philosopher Pirate)". The first verse is pulling lines from a 1926 era song "White House Blues" recorded by Charlie Poole and the North Carolina Ramblers. It is referring to the McKinley Assassination and the subsequent Theodore Roosevelt Administration. Dylan's latter day work is full of references to various source materials from old songs. For me researching these little gems has been a source of pleasure and an education as well. Dylan has an encyclopedic knowledge that he imparts obliquely, allusively and elusively. The verse about being wed to a prostitute has been explained as referring to the Prophet Hosea and his wife Gomer who was an unfaithful woman. The age of 12 is close to bar mitzvah. Is Dylan referring to his family of origin religion? Perhaps. The other line that I didn't quite get was "Key West is on the horizon line." An explanation that I like is that this island refuge and paradise is always out in front of the wanderer forever receding in front like a wavering mirage in the distance. The lazy accordion and the length of the song lend to the hypnotic effect of the imagery of the heat and potent flowers. Another "Shelter From the Storm"..."if you've lost your mind you will find it there."
  • Jm from Szeged, Hungaryabout 'married a prostitute at 12', wasn't this about his bar mitzvah, being made part of the Jewish religion? Note 'forced to marry' and 'we're still friends'. Ain't it cute...?.. --- And McKinley was Muddy Waters' name - although I see no further Muddy connections here.
  • Pj from SfThe verse about McKinley is a slight re-write of lines from "White House Blues" a folk song by Charlie Poole and others about McKinley's assassination in 1901, another song like Murder Most Foul about an American President assassinated. "Jimmy" also could refer to Jimmy Rogers who wrote the song from which Dylan's album is titled, "My Rough and Rowdy Ways".
  • John W from ScotlandThe song starts with the doctor asking McKinley if he has anything to confess. McKinley was US president who was assassinated and it seems to me to reference Murder most Foul. McKinley portrayed himself as the people’s president like Kennedy. However he was also responsible for the Spanish American war and conquered and colonised Cuba, Puerto Rico, Hawaii and the Phillippines for the US and he later became closely associated with big business interests.
    Key West is the nearest point in the US to Cuba and it had a significant Cuban population. It has a naval base and was important during the Spanish American War. It was also important during Kennedy’s Cuban missile crisis. Following the assassination the FBI and later the CIA were set up to protect the president, which offers another link to Murder most foul. So McKinley is a ‘man of contradictions’.

    I think this song is about a poisoned paradise where the rich and famous have gone to wear hibiscus flowers in their hair and over-dress in the heat. And ‘nobody has to think too much about Desolation Row’
  • Sam from Thailandsuffice to say thanks for the comments about European radio stations which got me thinking. This song now makes more sense, to me, than it did an hour ago.

    'i got both my my feet planted square on the ground
    got my right hand high with the thumb down
    Such is life, such is happiness.'

    brutal, and the bit about the prostitute?

    hes still got it basically, and he got it off of the radio
  • Sam from Thailandhard to write about this without being way off but thanks to the comment about Pirate Radio Key West, I like to imagine hes come here on holiday, heard the phrase, and gone with it.

    strange lyric early on that hes looking for love but almost inmediately hes blind with it, whats happened? music, like most of the ones he name drops, and since his epiphany he has a purpose in life, even if it means he must be alone.

    from the sixties to the 80s for many the key to the enchanted land was luxembourg and budapest radio as the comments below show! that really helped with my understanding. the philosopher pirate speaker at the end of his life reminded by every signal of music and death and he plays both off against the middle, hoping to pick up that pirate radio signal.
    the healing virtues of the 'wind'
    for many the radio and pirate radio was a magical thing
  • Tim Reynolds from Cardiff, WalesBd is right. Radio Luxembourg broadcast all through my childhood and was one of the first commercial broadcasters in Europe. Spent many Sunday nights listening to the "Top Twenty Show" on my transistor radio under my pillow so my parents couldn't hear.
  • Bd from PolandThere was famous pirate radio station coming out of Luxemborg from 60-80. It was often listend in Soviet Union, especially in Budapest (there was special relay), Prague or Warsaw. You can read in Wikipedia: 'radio Luxemborg was an important forerunner of pirate radio'. Sorry for my English.
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