Key West (Philosopher Pirate)

Key West

Bob Dylan’s Last Album “Rough And Rowdy Ways” Lyrics


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
Heard it on the wireless radio
From down in the boondocks – way down in Key West

I’m searchin’ for love and inspiration
On that pirate radio station
It’s comin’ out of Luxembourg and Budapest
Radio signal clear as can be
I’m so deep in love I can hardly see
Down in the flatlands – way down in Key West

Key West is the place to be
If you’re lookin’ for immortality
Stay on the road – follow the highway sign
Key West is fine and fair
If you lost your mind, you’ll find it there
Key West is on the horizon line

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
It might not be the thing to do
But I’m stickin’ 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 grow everywhere here
If you wear one put it behind your ear
Down on the bottom – way down in Key West

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

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
The tiny blossoms of a toxic plant
They can make you dizzy – I’d like to help ya but I can’t
Down in the flatlands – way down in Key West

The fishtail palms (1) and the orchid trees
They can give you the bleedin’ heart disease
People tell me – I oughta try a little tenderness
Amelia Street – Bay View Park
Walkin’ in the shadows after dark
Down under – way down in Key West

I play the gumbo limbo spirituals (2)
I know all the Hindu rituals
People tell me that I’m truly blessed
Bougainvillea bloomin’ in the summer and spring
Winter here is an unknown thing
Down the flatlands – way down in Key West

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

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 Mallory Square
Truman had his White House there
Eastbound – westbound
Way down in Key West

Twelve years old and 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 in the bottom – way down in Key West

I play both sides against the middle
Pickin’ up that pirate radio signal
I heard the news – I heard your last request
“Fly Around my Pretty Little Miss” (3)
I don’t love nobody – gimme a kiss
Down at the bottom – way down in Key West

Key West is the place to be
If you’re lookin’ 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


© 2020 by Special Rider Music

(1) Caryota [also known as Fishtail Palm] is a genus of tropical plants with thirteen different species, belonging to the palm family (Arecaceae). It is the only genus in the family that has true bipinnate leaves. It is a toxic plant. The whole plant contains calcium oxalate crystals in the form of needles that if chewed or eaten can cause a burning sensation in the mouth. Contact with the skin can cause burning, itching and severe dermatitis.

(2) Gumbo limbo spirituals = Spiritual chants from South Florida islands natives. Gumbo limbo refers to the tree from which the rubber or the turpentine essence are extracted, and it is the popular name that the natives gave to the tree species “Bursera simaruba”, also known as Chaca. It’s a kind of species typical of the tropical regions of the Americas, from southern Florida to Mexico and the Caribbean to Brazil and Venezuela.

(3) “Fly Around my Pretty Little Miss” = Traditional folk song already recorded back in the 1920s. Among the first recordings of this song is a version of the “Frank Blevins And His Tar Hell Rattlers String Band” from Ashe County, North Carolina. The name of the band was improvised during the Columbia recording session in the city of Atlanta in 1927, in which the 16-year-old violinist Frank Blevins, his older brother and guitarist Ed Blevins and the instrumentalist Fred Miller on the banjo were the performers. The band’s playing was apparently inspired by shots of corn liquor taken from a convenient jug. Recently, this year, it was recorded by Gillian Welch (with David Rawlings collaboration) and included in an album titled “All The Good Times (2020)”, in which they also cover “Oh Babe It Ain’t No Lie”, “Senor” and “Abandoned love.”

Drawing captured from Bob Dylan’s Key West video on Youtube

Some interesting comments from users (right or wrong) found about this song on Songfacts website:

Barry Mccollom from Plano, Tx:

Just 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, Hungary:

About ‘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 Sf:

The 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 Scotland:

The 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.”

Pigeon Key Highway Bridge

Apparently, being forced at age 12 to marry a prostitute also may refer to a common custom during the 17th and 18th centuries in some European countries that consisted of forcing convicted juvenile delinquents to marry prostitutes, offering them freedom in exchange, with the sole condition that they accept said imposition.

As an interesting reference, you can follow the following link:

Pigeon Key Old Bridge

The Hypnotist Collector

2 thoughts on “Key West (Philosopher Pirate)

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s