The Best of 2020: Dylan’s “Key West (Philosopher Pirate)”

This is the first in a series of year-end posts about some favorite works of art that I first encountered in 2020. It will be followed by pieces on my favorite books and films.

Bar stools at the legendary Captain Tony’s Saloon in Key West, Florida

2020 has sucked for all sorts of reasons. Observing strict COVID-19/social distancing guidelines means that I’ve spent less time with family and friends than ever before; what I assumed would be my busiest and most productive year as an artist has ended up being the exact opposite; and, as an adjunct college professor, I’ve had to re-learn my trade from the ground up as I’ve transitioned into teaching classes online exclusively. In order to maintain perspective, I’ve had to remind myself that I’ve been a lot luckier than some other folks I know: Unlike friends and colleagues who have been laid off, I’ve at least been able to work from home and continue earning a steady paycheck. Being at home more often also means that I’ve spent more time consuming art — mainly, literature, music and movies — than I have in a single calendar year in decades, maybe ever. The work of art that I’ve turned to for comfort more than any other during this tumultuous time has been “Key West (Philosopher Pirate),” the penultimate track from Bob Dylan’s terrific Rough and Rowdy Ways album, which was released in June. I’ve listened to this song literally hundreds of times already, often on headphones while walking around the north side of Chicago wearing a quarantine mask, and it’s never failed to be a transporting and cathartic experience.

I think it’s productive to regard “Key West” as Dylan’s own version of “Over the Rainbow,” a song originally written by Harold Arlen and Yip Harburg for The Wizard of Oz and sung by Judy Garland’s Dorothy in response to her Auntie Em’s advice to find a place where there isn’t any trouble. Dylan, who described “Over the Rainbow” as “cosmic” in his 2004 memoir Chronicles Volume 1, makes an explicit nod to The Wizard of Oz in “Key West” when he sings, “I’ve never lived in the land of Oz / Or wasted my time with an unworthy cause.” Beginning with a disturbing description of hearing the assassination of William McKinley on a pirate radio station, Dylan’s song specifically details the act of traveling to Key West, a destination the narrator posits as a mythical place free of trouble, a “paradise divine” that appears “on the horizon line.” The subject of the song is the thin line between life and death, and Dylan uses Key West, a place where he apparently spent a considerable amount of time decades ago, as a metaphor for some kind of peaceful afterlife. The lyrics and Dylan’s phrasing are perfect: There are literally dozens of magical vocal moments scattered across the song’s nine-and-a-half minutes (e.g., “…if you got something to confess,” “Bougainvillea blooming,” “…gold fringes on her wedding dress,” etc.). But what truly elevates the track to heaven’s door, to that rarefied sphere of Dylan’s greatest achievements, is the genius accordion playing of Donnie Herron, the multi-instrumentalist and stealth MVP of Dylan’s live band for the past 15 years. Herron’s accordion here becomes the aural personification of a gentle Florida breeze, warmly embodying the “healing virtues of the wind” that Dylan so memorably sings about.

“Key West” also has meaningful and substantial connections to “Murder Most Foul,” the already-notorious, 17-minute epic about American popular culture in the wake of JFK’s assassination that follows it on the album. In addition to being concerned with the murders of Presidents and the act of listening to the radio, both songs also share similar lyrics: The phrases “down in the boondocks” and “going down slow” in “Key West,” for example, cleverly become literal song titles that are quoted in “Murder Most Foul.” Conversely, some of the lines in “Murder Most Foul” (e.g., “the man who fell down dead like a rootless tree”) appear to have been composed in pointed contrast to certain lines in “Key West” (e.g., “I’ve got both my feet planted square on the ground”). But the most important connection between the songs comes in the “Key West” lyric “I heard your last request,” which seems to refer to the final, self-reflexive line of “Murder Most Foul” (after a litany of other requests: “Play ‘Murder Most Foul'”). It is as if the narrators of the songs are in dialogue with each other — the narrator of “Key West” hearing and fulfilling the dying wish of the narrator of “Murder Most Foul” (who may be JFK himself) — thus creating an eternal two-song circle within an album full of other such circles (add the Julius Caesar-themed “Crossing the Rubicon” to these two, for instance, and you have a trilogy dealing with political assassination). Making these kinds of connections has always been part of the fun of listening to Bob Dylan, of course, but the songs on Rough and Rowdy Ways offer an exceptionally intricate, Joycean web in which listeners can get lost if they so choose. And I emphatically choose to do so. Such is life, such is happiness.

For those who don’t already own Rough and Rowdy Ways (and, if you don’t, what’s wrong with you?), you can listen to “Key West (Philosopher Pirate)” on YouTube here:

You can read more of my thoughts on Rough and Rowdy Ways here. My buddy (and Flickering Empire co-author) Adam Selzer expounds on the connections between “Key West” and “Over the Rainbow” at length here.

For the record, my top five favorite albums of the year are:

5. Emma Swift – Blonde on the Tracks
4. Haim – Women in Music Pt. III
3. Run the Jewels – RTJ4
2. Fiona Apple – Fetch the Bolt Cutters
1. Bob Dylan – Rough and Rowdy Ways


About michaelgloversmith

Filmmaker, author and Film Studies instructor. View all posts by michaelgloversmith

7 responses to “The Best of 2020: Dylan’s “Key West (Philosopher Pirate)”

  • Bob Jope

    Key West is ‘the place to be’, but it’s also ‘on the horizon line’. It’s both there and not there, easy to describe but inaccessible, both utopia and a place of death.The name is an Anglicisation of the Spanish cay hueso, ‘Island of Bones’ ( Spanish settlers originally called Key West Cayo Hueso, referring to the bones of the Calusa Indians who had once lived there)…This is a wonderfully expressive response to an extraordinary song, one that makes me think, too, of what Dylan told the NY Times: ‘The song is like a painting, you can’t see it all at once if you’re standing too close,’ he said, ‘the individual pieces are just part of a whole.’ Bob J

    • michaelgloversmith

      Thanks so much for reading closely, Bob. It’s nice to know that other people feel the same way.

      • Bob Jope

        Not sure how else to send you this (something I wrote a whileback):

        Key West, Island of Bones

        ‘The song is like a painting, you can’t see it all at once if you’re standing too close,’ Dylan recently told The New York Times, ‘the individual pieces are just part of a whole.’

        In a number of his most striking songs since 2001 Dylan has adopted the dramatic monologue form as a way of entering and articulating alternative personae, intimations of the ‘multitudes’ he celebrates on his latest album, Rough and Rowdy Ways, quoting Walt Whitman in its opening song, a kind of overture whose leitmotifs echo through the collection: ‘I Contain Multitudes.’

        As Robert Langbaum argued in The Poetry of Experience: ‘The standard account of the dramatic monologue is that Browning and Tennyson conceived it as a reaction against the romantic confessional style. This is probably true. Both poets had been stung by unfriendly criticism of certain early poems in which they had too much revealed themselves; and both poets published, in 1842, volumes which were a new departure in their careers and which contained dramatic monologues. The personal sting was probably responsible for Tennyson’s decade of silence before 1842; it was almost certainly respon- sible for the disclaimer attached by Browning to his 1842 Dramatic Lyrics: “so many utterances of so many imaginary persons, not mine.”’

        Dylan’s ‘utterances of so many imaginary persons’ range from the wry, worldly wisdom of ‘Floater’ to the embittered ‘Working Man’s Blues’, from the aching, guilt-driven ‘Nettie Moore’ to the sometimes snarling husband in ‘Long and Wasted Years.’

        ‘Key West’ is, I think, not just the latest but also one of Dylan’s most extraordinarily potent enactments of an ‘imaginary’ and yet deeply authentic voice.

        In some ways the song calls to mind Matthew Arnold’s ‘The Scholar Gypsy’ (scholar/philosopher; gypsy/Pirate), a poem that itself echoes Keats’ ‘Nightingale’ (coincidentally a poem Christopher Ricks compares with ‘It’s Not Dark Yet’) in juxtaposing a bleak actuality and an imagined, or imaginary, immortality: ‘this strange disease of modern life…the infection of our mental strife’, alongside the inevitability of fading youth, highlight by contrast the gypsy’s ‘unconquerable hope’ in blissful solitude – forever.

        In Arnold’s narrative poem the scholar gypsy doesn’t speak, of course, whereas Dylan’s dramatic monologue enables his ‘philosopher Pirate’ to reflect, reminisce, assert and eulogise in his comparably – if not consistently – blissful state.


        The Pirate’s monologue seems to be, in part, a confession, prompted by an old man’s memory of McKinley’s assassination and his doctor/priest’s command:
        …McKinley – death is on the wall
        Say it to me if you got something to confess
        The prompt sets off a series of memories and reflections, calling to mind but far less bitter than T S Eliot’s ‘Gerontion’, a monologist wandering through a labyrinth of ‘windy spaces’ while he’s ‘read to by a boy’, where the Pirate has his radio for company and, perhaps, solace, as, he too wanders in, as Robert Glover has it – referring to the whole album – ‘a work of seemingly bottomless depth, a haunting liminal space where past, present and future overlap’.

        The Pirate’s peace of mind isn’t an easily won, or easily sustained thing, something we’re alerted to by his apparent contradictions within a few lines:
        I’m searchin’ for love…
        I’m so deep in love
        The contradictions here and elsewhere (he contains multitudes) render him ‘real’. Where Arnold’s gypsy is, as the poet confesses two-thirds into the poem, a fantasy, his immortality mythical, Dylan’s Pirate is, for all his celebrations of the sublime, toughly real, an old man of the sea who now has, he’s keen to remind us, ‘both my feet planted square on the ground.’ (Or is it for ‘Most of the Time’?)

        The monologue’s fragmentedness and knotty interconnectedness, its pauses and sudden shifts of emphasis, from detached reflection to sudden intimacies, call to mind an old man in an afternoon Florida bar, gnarled by experience, worldy-wise, happy to reminisce while, in his repetitiveness, apt to (age? The drink?) over-emphasise, over insist.


        Dylan’s ways of saying things contribute hugely to the song’s effect, how we hear the voice and are convinced by it. It’s a brilliant performance. Frank Kermode talks about Shakespeare’s soliloquies ‘dramatising thought’, and that’s exactly what we have here. A wonderful example, I think, is when the old man’s tone shifts into sudden intimacy, as though he leans closer into us with a sly nod and a wink – you can almost hear him breathe – to offer a kind of secret boast, one that no-one else in the (probably nearly empty) bar is meant to hear – after all, they might know him too well, and they’ve probably heard it all before:
        I play the gumbo limbo spirituals
        I know all the Hindu rituals
        People tell me that I’m truly blessed
        It’s an intimacy that’s characteristic of a dramatic monologue, as it is of a Shakespearian soliloquy where the speaker wins us over by sharing his or her private thoughts with us: even a character as appalling as Iago, a psychotic monster, wins us over ( we ‘suspend moral judgment’ as Lagnbaum has it) by letting us in on his secrets.

        Just as convincing in ‘Key West’ are the moments of imparted knowledge, the random gobbets of insider information that the ‘Pirate’ offers, like a drunk I met in the park just recently who insisted on telling me things he knew were ‘facts’, things that the world at large of course knew nothing about, or denied (from the ‘true’ cause of coronavirus to the ‘bomb’ that set off the disaster in Beirut):
        The tiny blossoms of a toxic plant
        They can make you dizzy…

        The fishtail ponds and the orchid trees
        They can give you the bleedin’ heart disease…

        I’ve suggested that ‘Key West’ is a confession (something I’ll return to) but it has, too, the manner of an incantation, a quietly meditative mood where reflections, assertions and reminiscences are linked by reminders of the location’s meaning – for the speaker – that chime like a leitmotif through the song’s nine minutes plus.

        That gentle, wistful chiming contributes much to the song’s impact, underscored by the easeful accordion and a background ‘choir’ we can just about hear. As Timothy Hampton (author of Bob Dylan’s Poetics: How the Songs Work) says: ‘I love the way the song begins on a major chord, but comes to rest on a minor chord every time we get to “Key West.” There’s something melancholy about that minor chord (like the minor chord at the end of the first line of “Don’t think Twice”): it’s a nice ending point, but it always suggests that the song could be opened up again. It never quite concludes with a grand sense of stability the way a major chord would.’

        Even McKinley’s violent death is recalled peaceably – ‘he was goin’ down slow’ – heard about from a distance, the security of Key West, and safely on the ‘wireless radio’, the same radio the speaker tunes into in his search for ‘love’ and ‘inspiration’ (anticipating the strength and reassurance called for from Mr Wolfman’ in ‘Murder Most Foul’). Perhaps that sense of love, in fact, is indeed provided by the music that the radio station offers:
        ‘I’m so deep in love…’
        Music as the ‘food of love’? Shakespeare’s Orsino goes on:
        That strain again! It had a dying fall:
        O, it came o’er my ears like the sweet sound
        That breathes upon a bank of violets
        The Pirate, in turn, delights in ‘the healing virtues of the wind’, virtues akin, perhaps, to the music on the airwaves that the Pirate searches for as he toys with the dial, ‘playing both sides against the middle Pickin’ up that Pirate radio signal’.

        Key West offers a kind of refuge, or relief, a haven at the end of a journey. While Eliot’s Gerontion is ‘an old man in a dry month…waiting for rain’, hoping vainly for some kind of spiritual release or salvation, Dylan’s Pirate rather than ‘waiting’ has reached somewhere ‘fine and fair‘ – ‘the place to be If you’re lookin’ for immortality’. Life and happiness, he tells us, are what he’s found, peace of mind – ‘If you lost your mind, you’ll find it (in Key West)’ – in what he calls ‘an enchanted land’.

        At the same time, just as he reminds us that he has, again, ‘both feet square on the ground,’ he’s insistent that he’s never lived in a fantasy world (’the land of Oz’) and tells us of tougher times, born on the wrong side of the tracks. Even as he tells us that, though, there’s a hint, I think, of the sly boasting I talked about earlier:
        Like Ginsberg, Corso and Kerouac
        Like Louie and Jimmy and Buddy and all of the rest
        The list of names suggests, as it drifts into vagueness – ‘all of the rest’ – not so much a loss of memory as a kind of hopeful but unconvincing assertiveness, reminding me of, for example, Harold Pinter’s Stanley in The Birthday Party trying to impress with his probably invented memory of a successful recital: ‘They were all there…’ Our Pirate wants glory by association but it’s not, in the end, fully won. I can almost hear a fellow drinker at the bar, muttering in response, ‘Yeah, and all the rest…’

        There’s a confessional undercurrent, too, of guilt and regret, implied when, for example, the Pirate’s told he should ‘try a little tenderness’: who has he upset, or hurt? And why can’t he ‘help’ someone he’d apparently like to? Why does he walk ‘in the shadows after dark’? Unable to sleep, kept awake by memories, or guilt?

        Wandering those streets he does what he thinks is ‘right’ or ‘best’: that ‘thinks’ is telling, suggesting perhaps a struggle, where ‘knows’ would be more certain, more confident. At the same time he’s ‘not that far from the convent home’: revealingly, not ‘my’ but ‘the’, and I can’t help but remember that in Shakespeare’s English ‘convent’ or ‘nunnery’ could mean a brothel – as in Hamlet, for example, quoted from more than once on Rough and Rowdy Ways. And ‘not that far’: is he forever haunted by a memory, something he can’t escape from, even in a ‘paradise divine’? Wandering midnight streets like Blake’s Londoner (in another ‘Song of Experience’), trying to do what’s right, manacled by memory.

        Then, towards the end, an unexpected, shocking revelation – perhaps a key to that haunting memory:

        Twelve years old and they put me in a suit
        Forced me to marry a prostitute

        Who are ‘they’? Was he brought up in the ‘convent home’ where ‘they’ forced him? The suddenness of the recollection again has a convincing authenticity about it, like something he’s been suppressing, trying not to talk about, but in the end, a buried memory, it slips out – or breaks out. Twelve years old: the Pirate’s remembering something like what today we’d call abuse. Dressed up like a sacrificial victim, put in a suit, forced to marry. He remembers it with a new particularity (unlike the vagueness of, say, ‘all the rest’ that I talked about earlier), including the bride’s gold-fringed dress, suggesting something of huge import, something he’s never entirely recovered from or come to terms with. There’s a whole new story here contained in just two lines – and they lead on to the next surprise:

        That’s my story but not where it ends
        She’s still cute and we’re still friends

        It’s almost as though he’s consoling or reassuring himself here, perhaps even as a kind riposte to whoever forced him (and her?) to marry: despite them, ‘we’re still friends’ – and I love that ‘cute’. Forced marriage to a prostitute may be ‘my story’ but, he adds with a degree of quiet defiance, it’s ‘not where it ends.’ It’s the defiance of a survivor: whoever ‘they’ are or were, they didn’t win.

        Whatever, leaving that story hanging, the Pirate returns – perhaps for more consolation – to the radio: ‘Fly around My Pretty Little Miss’, an old mountain song sung more recently by Gillian Welch (on an album that includes ‘Señor’ and ‘Abandoned Love’), or simply ‘My Pretty Little Miss’ sung Appalachian style by Patty Loveless, with this intriguing parallel:

        Mama says he’s not my type
        He really loves another
        But he’s gonna marry me
        When I turn twelve this summer

        Twelve years old…If it’s Loveless, the name itself could set off a sudden twinge of bitterness, that in turns prompts a pathetic demand (as the drink takes hold?):
        I don’t love nobody – gimme a kiss

        A bitter memory, an attempt at consolation, an escape into music, a song that reminds him that he loves nobody and, of course, nobody loves him. He’s at his lowest, ‘Down at the bottom – way down’. ‘Way Down,’ though, as Elvis sang, is also ‘where the music plays’. With that, the Pirate pulls himself together, takes a breath and reminds us – and himself – that

        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

        The horizon line, the vanishing point, coincidentally something strikingly visualised in a number of Dylan’s paintings, and beautifully enacted in the song’s own slow vanishing, a fading accordion and still that distant choir. As it vanishes, its mysteries remain, and we’re left with what Timothy Hampton calls a ‘fundamental ambiguity’:

        ‘Key West is the place to be, but it’s also “on the horizon line.” It’s both there and not there, easy to describe but inaccessible, both utopia and a place of death.’

        ‘There and not there‘…‘I’m not there, I’m gone…’

        Timothy Hampton again, puzzling over what he calls ‘the question of the “Pirate”’:

        ‘The pirate here is “pirate radio,” so, a form of musical broadcast (we could imagine it coming in from Cuba, as well as Budapest). But the title says “philosopher/pirate.” So the narrator sees himself as a kind of pirate, some type of romanticized self. But what does that self-description have to do with pirate radio? I can’t get my head around it…I can’t get it clear in my mind (maybe that’s the point).’

        A coda: purely coincidental but enjoyable, I thought. Jonathan Raban’s voyage around the States, Hunting Mister Heartbreak, winds up in Key West – ‘ a blameful city of guises and disguises’ – reminding us that the name is an Anglicisation of the Spanish cay hueso, ‘Island of Bones’ ( Spanish settlers originally called Key West Cayo Hueso, referring to the bones of the Calusa Indians who had once lived there) and finally trying to book himself, rather unseriously, a tomb, not a room, in the local cemetery.
        Given the price over the phone, he asks, ‘Is it for eternity?’
        ‘Yeah,’ he’s told.
        I wanted to add, ‘Eternity? You might call it Paradise.’
        Key West, then: a place or a space for ‘eternity’ – or immortality….
        Raban enjoys Key West’s bourgainvillea and hibiscus, too, going on to say, ‘I could think of no better site for an American ending. After the continuous motion of life in the United States, the striving and becoming, you’d land up here in sunny indolence…within the sound of the sea.’

  • MKB

    Thanks both for what you write, it helps unpack the meaning and different viewpoints are always interesting to shed various lights on things, like this great song from a great album. I was in Key West once, and identify with the strange-nesses of the place, out on the end of events, facing Cuba. I remember it was a long drive to reach it, but I did, eventually. It had a liminal quality as suggested, a bit like this one, writing into an open ended space. Thanks again for your words.

  • The 80 Greatest Bob Dylan Songs (in Honor of His 80th Birthday) | White City Cinema

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  • Zuun Zug

    I’m crazy about this song… Thanks for this very interesting article.

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