Song of the Day #4,520: ‘Key West (Philosopher Pirate)’ – Bob Dylan

In terms of longevity and output, Bob Dylan is the standout among this week’s group of old men. The 79-year-old released his 39th studio album earlier this year, as he nears his 60th year of recording.

Rough and Rowdy Ways is Dylan’s first album of original material since 2012’s Tempest. He spent the time in-between releasing three albums of standards (including the three-disc Triplicate), but clearly playing Frank Sinatra was not going to be Dylan’s final creative act.

If Rough and Rowdy Ways does turn out to be the Bard’s final album it will make for a nice swan song. It finds Dylan in an alternately playful and elegiac mood and is full of enough lyrical flights of fancy to keep Dylanologists busy for years.

Several of these songs fall into the familiar snarly blues format Dylan has favored in his later years, and with some of those topping out over 6 minutes, they wear on my patience. But other tracks are musically more subtle and unexpected.

Setting aside ‘Murder Most Foul,’ the 17-minute epic about the JFK assassination that fills out the entire second disc, this album’s spiritual closer is the lovely ‘Key West (Philosopher Pirate)’. It’s about the city, sure, but a hundred other things as well, from William McKinley’s assassination to Dylan’s Bar Mitzvah.

[Verse 1]
McKinley hollered, McKinley squalled
Doctor said, “McKinley, death is on the wall
‪Say it to me, if you got something to confess”
‪I heard all about it, he was going down slow ‬
‪I heard it on the wireless radio ‬
‪From down in the boondocks way down in Key West
‪I’m searching for love, for inspiration ‬
‪On that pirate radio station
‪Coming out of Luxembourg and Budapest ‬
‪Radio signal, clear as can be
‪I’m so deep in love that I can hardly see ‬
‪Down on the flatlands, way down in Key West

[Chorus 1]
‪Key West is the place to be ‬
‪If you’re looking for immortality ‬
‪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

[Verse 2]
‪I was born on the wrong side of the railroad track
‪Like Ginsberg, Corso and Kerouac
‪Like Louis and Jimmy and Buddy and all the rest ‬
‪Well, it might not be the thing to do ‬
‪But I’m sticking with you through and through ‬
‪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 ‬

[Chorus 2]
‪Key West is the place to go
‪Down by the Gulf of Mexico ‬
‪Beyond the sea, beyond the shifting sand
‪Key West is the gateway key ‬
‪To innocence and purity ‬
‪Key West, Key West is the enchanted land

[Verse 3]
‪I’ve never lived in the land of Oz ‬
‪Or wasted my time with an unworthy cause ‬
‪It’s hot down here, and you can’t be overdressed
‪Tiny blossoms of a toxic plant ‬
‪They can make you dizzy, I’d like to help you but I can’t
‪Down in the flatlands, way down in Key West ‬
‪Well, the Fishtail Palms, and the orchid trees
‪They can give you that bleeding heart disease
‪People tell me I ought to try a little tenderness ‬
‪On Amelia Street, Bayview Park ‬
‪Walking in the shadows after dark ‬
‪Down under, way down in Key West ‬
‪I played Gumbo Limbo spirituals
‪I know all the Hindu rituals ‬
‪People tell me that I’m truly blessed ‬
Bougainvillea blooming in the summer, in the spring
Winter here is an unknown thing
Down in the flat lands, way down in Key West

[Chorus 3]
Key West is under the sun, under the radar, under the gun
You stay to the left, and then you lean to the right
Feel the sunlight on your skin, and the healing virtues of the wind
Key West, Key West is the land of light

[Verse 4]
Wherever I travel, wherever I roam
I’m not that far from the convent home
I do what I think is right, what I think is best
Mystery Street off of Mallory Square
Truman had his White House there
East bound, West bound, way down in Key West
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
Down on the bottom, way down in Key West
I play both sides against the middle
Trying to pick up that pirate radio signal
I heard the news, I heard your last request
Fly around, my pretty little Miss
I don’t love nobody, give me a kiss
Down on the bottom, way down in Key West

[Chorus 4]
Key West is the place to be
If you’re looking for immortality
Key West is paradise divine
Key West is fine and fair
If you lost your mind, you’ll find it there
Key West is on the horizon line

7 thoughts on “Song of the Day #4,520: ‘Key West (Philosopher Pirate)’ – Bob Dylan

  1. Dana Gallup says:

    Boy, Dylan’s later years output has really become three chords, a 5 note vocal range and the snooze.

  2. andrea katz says:

    I have to agree. I could not have been a bigger fan but I’ve not found anything worthwhile in over 25 years. Just not the fascinating lyrics and musical genius that I revered. This hurts my heart. Such faded glory.

    • Clay says:

      I have to disagree, especially because Love & Theft, Time Out of Mind and Modern Times are all within the past 19-23 years. Those are stone-cold classics. The lyrics on the new album are quite good, though I agree the music has gotten a bit monotonous.

      • Dana Gallup says:

        You see, when you start throwing around terms like “stone-cold classics” you lose any claim to credibility or objectivity. While those albums were quite good, particularly compared to something like this, to earn the term “classic” let alone “stone-cold classic,” there needs to be far broader love of the work beyond critics and the most ardent of fans (or arguably in some cases apologists). By the way, I don’t limit this to Dylan. Many artists I love, including Springsteen, Paul Simon, Elton John and Elvis Costello, have put out some decent stuff over the past 30 or so years, but their stone-cold classics did not cross 1990.

        • Clay says:

          I’d agree with you if we were talking about Together Through Time or Tempest or anything from the 80s or 90s. But those three albums are widely accepted as a renaissance in Dylan’s career and one of his creative peaks. Time Out of Mind won the Best Album Grammy, and all three albums sold very well (Modern Times even debuted at #1, making him the oldest artist to ever do so).

          Next to Bringing it All Back Home, Highway 61 Revisited and Blonde on Blonde in the mid-60s, this was the best three-album span in his entire career.

          • Dana M. Gallup says:

            There is a difference between an album that is a renaissance, critically praised, award winning or (somewhat of) a commercial success and a “stone-cold classic.” Of course, I’m talking to not only a huge Dylan fan, but also the guy who considers Mama Mia II a masterpiece 🙂

          • Clay says:

            Well, as a huge Dylan fan, I would argue that the phrase applies to his best work, and I consider those three albums among his best work.

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