When I Paint My Masterpiece: the meaning of the lyrics and the music

By Tony Attwood

This song, which pairs with Watching the River Flow, in terms of its consideration of artistic process, comes from 1971, and gives us a problem, in that it has changed quite a few times.  Rather like the masterpiece painting where x ray examination can reveal the changes that the genius painter made as he went along – not always (from our viewpoint) for the better, so here we can see the songwriter playing with his work, seeing where it might go.

However the notion of changing a work, even after it is finished for the first time, is one that many commentators find difficult.  In our society we are used to a final finished piece. Surely, they seem to argue, the work should be the work, finished off in some complete form, like a TV show, a movie, a car or a table lamp. You design it, you make it, it is.

But in works of art that is never right, and Dylan is the absolute supreme re-worker of his own material, as the live shows endlessly show.

So should we worry that on one occasion the streets of Rome are full of trouble, and another they are full of rubble?  Probably not, although there are one or two changes that are interesting to say the least, and one that is utterly fascinating.

The fact is that Dylan’s images can relate to real things he’s seeing and hearing, and other things that just pop into his mind at the moment.  Indeed part of the mark of a genius is what he observes, and part is this odd stuff that pops into the mind.  Part is the ability to re-work and find ever more interesting bits.

If we take the two opening lines – “filled with rubble” and “filled with trouble” both work.  The rubble of the fallen monuments of the Republic and the Empire, the trouble from the uprisings of greedy and self-centred men who would put themselves before the extraordinary achievements of the Republic, to the collapse of the Empire as the Goths came knocking on the door.

Both words (rubble and trouble) can lead onto the ancient footprints being everywhere.

So we have in the first verse a masterpiece of reference and change…

Oh, the streets of Rome are filled with rubble
Ancient footprints are everywhere
You can almost think that you’re seein’ double
On a cold, dark night on the Spanish Stairs
Got to hurry on back to my hotel room
Where I’ve got me a date with Botticelli’s niece
She promised that she’d be right there with me
When I paint my masterpiece

The Scalinata di Trinità dei Monti (Spanish Steps, Dylan calls the “stairs”) take you (if you have the energy) up the steep hill from the Paizza di Spagna to Trinità dei Monti.  135 steps, not really a climb to do on a cold dark night unless you are chasing shadows and ghosts – which is fun in itself.  But most of the time there are not cold dark nights in Rome.

But that’s only the start of the fun, because then we had originally a pretty little girl from Greece who became Botticelli’s niece.  Just a phrase that popped into his head?  Maybe, maybe. But (and you are going to have to stay with me for a moment if you want to get to grips with this idea) here is another explanation.

I doubt that Dylan just looked at the Coliseum, and the Spanish Stairs and said, “hey that’s nice” and walked on.  I don’t mean I think he stayed with a guide book, but this is a guy who knows and enjoys his history and his literature, I suspect he knows a lot about art too.

And so I suspect the real origins of Botticelli’s niece come from his painting The Birth of Venus, which was commissioned by the Medici family.   As the guidebooks and histories point out Pliny the Elder (the great writer, scientist and philosopher who died while recording his scientific observations on the eruption of Vesuvius) suggested Alexander the Great offered his mistress as the model for the nude Venus to be painted by Apelles.  But then noting that Apelles had fallen in love with the girl, gave her to the artist.

Botticelli, in painting his version of the Birth of Venus, was seen as recreating the earlier lost masterpiece and in 1488 Ugolino Verino wrote a poem describing Botticelli as a born-again Apelles.

The actual model for Botticelli’s Birth of Venus was not his niece but Simonetta Cattaneo Vespucci, who it seems had a “relationship” with two of the Medicis.  Linking  Birth of Venus with the great days of the Republic makes the model in the picture a symbol of the continuity of the Republic, the Empire and the Eternal City.

It’s a famous tale for anyone interested in the art of the Republic and the Empire and I think turning Botticelli’s Venus into Botticelli’s niece is a nice piece of fun for Dylan, which gives him a handy rhyme.  And why not?

We are very much in the world of Dylan the Tourist.  He won’t have seen Birth of Venus in a trip to Rome, but Dylan had Italian connections all the back from his time with Suze Rotolo and his trip to Italy looking for her.  Indeed the stories around Freewheelin are full of Italy.  And besides “Masterpiece” does have the line Train wheels runnin’ through the back of my memory.

But I’m getting ahead of myself…

Oh, the hours I’ve spent inside the Coliseum
Dodging lions and wastin’ time
Oh, those mighty kings of the jungle, I could hardly stand to see ’em
Yes, it sure has been a long, hard climb

I’ve always wondered with that line of the long hard climb, if we are not back to the Spanish Steps!  Surely we are.

But then so much of this song is looking back

Train wheels runnin’ through the back of my memory
When I ran on the hilltop following a pack of wild geese
Someday, everything is gonna be smooth like a rhapsody
When I paint my masterpiece

The geese story is, I think, not quite understood in every review of this song.  The story is that when the Republic of Rome was under attack from the Gauls in 390BC (which is to say in the fabled origins of the Republic, long before the days of the Empire) Rome seemed about to fall and the Romans were besieged.  Despite low food supplies during the siege the Romans kept their sacred geese fed, and this turned out to be a shrewd idea, because as the Gauls attacked, the geese honked as they do, woke up the guards, who then resolutely defeated the attackers.

The Gauls gave up their attack and withdrew, Rome was rebuilt, and the sacred geese were remembered forever with an annual parade in which a golden goose is the heart of the celebration.

Dylan then is remembering the story, which of course is a central part of Roman mythology.  You can’t read a guide book without finding it somewhere.

But then strangely he seems to dismiss it all…

Sailin’ round the world in a dirty gondola
Oh, to be back in the land of Coca-Cola!

Suddenly we are out of Rome – there are (just to be clear about this) no gondolas on the Tiber, that’s Venice.  Indeed going for a sail along the Tiber is just plain dull and really not worth the effort.  And besides, certainly for me, each time I’ve been to Venice there are not dirty gondolas; the competition to get the tourists into gondolas is very strong, and brightness and colour is part of the deal.  (The water buses are cheaper though, and just as much fun).

So what is this about?  Leaving the history, the romance, the beauty, the total story of the Republic and Empire, for sugar, colour, flavouring and water plus a mistake about where the canals are???

I think there is a good reason why the recording on Greatest Hits removes those lines – they have no real connection with the song.   They are just Dylan having a laugh.  And it is a real downer on Botticelli etc etc.  My own view, for what it is worth, is that it was an attempt at irony, and as such it is a good couplet, but open to misinterpretation.  So the version without it was used on the album.

And then he leaves and carries on with the tour of Europe.  The final verse seems to be a reflection on the art of Italy.  He has seen it, he knows he can create masterpieces in his chosen art form.  Brussels, the newspapermen and the fans are just a distraction.  And the women are nothing like the Venus he has been contemplating…

Clergymen in uniform and young girls pullin’ muscles
Everyone was there to greet me when I stepped inside

There is one other couplet that I really have always enjoyed…

Newspapermen eating candy
Had to be held down by big police

Dylan is having fun, but also saying he knows it doesn’t have to be like this

Someday, everything is gonna be diff’rent
When I paint my masterpiece

There was however a line that appears to have been cut from this ending, With a picture of a tall oak tree by my side – the reference to the Zen tradition of using one aspect of nature alone to understand everything.  Cutting the pretty little girl from Greece was, to my mind (and of course all this ruminating is just my reaction to the song) was a good move (not that in any seriousness could I tell Dylan what was better or worse in his writing) but losing the oak tree was not so good, at least in my world.  It is an image of a way of contemplating the world – the only thing that is wrong with it is that it is from a totally different culture.  Not from Italy or Belgium, but from China.

And there is another cross reference that I had completely failed to see, until reminded of it through an excellent review  on Expecting Rain, which if you are seriously interested in this song you really ought to read.

In ‘Childe Harold’s Pilgrimage’  written in 1818 by Lord Byron, the poet (and here I quote from the Expecting Rain review)  contemplates the ruins of ancient Rome and finds nothing but chaos – broken dreams and relics of ancient cruelty….

Byron perceives the city as a whole as a space strewn with fragments and debris, visible signs of decayed power testifying to the vanity of human aspirations

The Expecting Rain review, written by Christopher Rollason (whose blog is always worth a read) sees the song as coming from a narrator who “has come to Europe and Rome in search of artistic fulfilment, hoping that with ancient scenes around him he will achieve the vision that will enable him finally to ‘paint his masterpiece’.”

That’s a very interesting vision.  I have approached the song seeing this as Dylan himself contemplating Rome and Italy, and the “paint my masterpiece” not being literally “paint” but a metaphor for his ultimate work of art – most likely of course his ultimate song or ultimate album as conveyed in the lines “Some day everything is gonna be smooth like a rhapsody When I paint my masterpiece”.

You can see it either way, just as you can see She promised that she’d be right there with me When I paint my masterpiece as a sexual phrase or as a phrase relating to the person who most artists or all genres have by their sides who support, put up with, and are a sounding board for their ideas.

So, a complex piece, with its own fun and some historical references too.  Difficult to transcribe into music.

But Dylan does it, but in so doing uses a technique that I think is unique within the Dylan repetoire.  He totally changes key between the second and third verse to reflect the change from Rome to Brussels.

We are clearly in A with A and E being the chords that the song for the first two verses, and then we slip backwards to the completely unrelated B flat.  It’s a different world.

It is not a very subtle technique, but it makes the point of the change of emphasis.  And the plane trip to Brussels wasn’t subtle.

As a final point….  This song was written in 1971.  In the summer of 1974 Dylan wrote Idiot Wind.  Maybe there was just something at the back of his mind that he knew was just a few years away from making its breakthrough.

All the songs reviewed on this site.




  1. Dear Tony: Thank you for your thoughtful and searching analysis of “Masterpiece.”

    May I make one suggestion? “Coliseum,” though an acceptable and common spelling, is generally inferior to “Colosseum,” which, I believe, must be regarded as the standard spelling when the writer is referring to the amphitheater in the center of Rome.

    Thanks again. Keep listening, thinking, and writing.

  2. Tony,
    Thanks for the awesome take on “Masterpiece” and to the reference to Chris’ review. I agree with what both of you have to say but I would add a comment to your observation about the “It sure has been a long hard climb” line. You wondered if this wasn’t another reference to the Spanish Steps, etc. but I always took it as a reference to “humanity’s” long hard climb from the days of feeding minorities with whom we do not agree to the lions–those mighty kings of the jungle. Of course, this leads the listener to wonder if we really have traveled all that great a distance. I mean, the whole song is ironic, right? Isn’t the narrator saying, in effect, “Yeah, no doubt, in and around everything else I do, I’m definitely gonna sit down and paint that masterpiece one of these days! Then everything will really be cool!” That’s why the song is so funny–and great! Like you, I love the lines such as “clergymen in uniform and young girls pullin’ muscle” and “newspaper men eatin’ candy” and having to be “held down by big police.” Kinda of like a day in the life of being Bob Dylan. Everywhere ya go somebody’s got something to say about it. Sheesh!

  3. One suggestion and one simple thought:

    It would be good to be explicit about references to particular versions, at least in officially released material. I know the verse changes, but don’t recall where they appear, other than from GHII and Cahoots.

    Not only is it one of my longtime favorites, but I think of it as “Dylan’s most optimistic song.” It’s an uplifting idea, that at any point in life inspiration might come or the time might arrive for one’s greatest work or most important contribution.

  4. In a world where everything is broken, an artist tries to paint a picture which unifies all the pieces into a a single masterpiece; in essence, he searches for “God’s plan’, a Oneness, as it were. Dylan hangs his art on the hook of ‘works’, having ‘faith’ that one day he will reach his ultimate goal.
    Indeed, each of his songs must be listened to in the context of all that he has written, and the pieces put together into the united vision that he seeks.

  5. To Dylan, fragmentation in art for fragmention’s sake, the hallmark of many Postmodernists, is the work of the devil, to employ a metaphor.

  6. I hear a man struggling his way through life waiting for his big break or rather his defining moment. I myself have taken a similar trip to that described in the song and can imagine the man in the song pressing on with the hope that he will experience that defining moment soon.

  7. Thank you for including the “tall oak tree” line in your analysis. I was always a bit stumped on that one, but your take on it with the Zen perspective tied into my own take on the song. Whenever he sings a about painting his masterpiece, it is tongue in cheek. It won’t really change him in any way. Although on the one hand, he sings that it will be a significant transformational experience, I think he also knows that’s not true. He’s being somewhat ironic about it, somewhat rye. He will still be the same person on a deeper spiritual level. Also, it is the plight of the artist that one is never done, there is always another work, song, poem, insight, inspiration, etc., and even if his next work is amazing, the public will probably say, “what has he done lately? What’s he doing next?” So, he’s tongue in cheek in my opinion, because Bob had already written several masterpieces, yet the journey continues and it could be argued whether or not “painting a masterpiece’ had ever really fullfilled him as a human being other than on an egoic level.

  8. Thanks so much for this! As an American traveling in Europe right now (and currently sitting outside the western facade of the cathedral of Notre-Dame in Paris!), I can easily identify with the bridge in this song. I started my trip in Rome so Masterpiece has been the theme. Although a fortnight of this trip is left, I miss my home: “Oh! To be back in the land of Coca-Cola!” Cheers!

  9. The reviews of Mr. Attwood and Dr. Rollason (link above) are quite wonderful; thank you. But attention to two words – “different” and “rhapsody” — suggests a slightly different reading. Dr. Rollason is certainly right; the narrator’s search for inspiration in the classical traditions of Europe was a wild goose chase; he was “wastin’ time.” But he does find true inspiration — back in his land of Coca-Cola, which is not only America but the American south (Coca-Cola is headquartered in the state of Georgia Sam. In one version of the song, “Victrola” makes the link to American music, including jazz and blues, more obvious.) The narrator already knows what his masterpiece will look like: *different* than what he’s seeing in Europe. He’s not going to erect a colossal classical structure; he’s just going to stitch some songs together (the word origin of “rhapsody”). He dismisses his European origins — with all due respect, how inspiring is a place where newspapermen eating candy have to be held down by big police? – in favor of American roots. One rendition mentions an oak tree that, yes, could be interpreted with reference to Zen tradition. But the Oak is the national tree of the United States. Also, if you ask Americans to name a rhapsody, they’re not going to think of Brahms and Liszt. They’re going to say “. . . in Blue” – Gershwin’s self-described “musical kaleidoscope of America.”

  10. Hear hear, Ruffo, the line referencing the land of coca-cola is poignant to me as one raised in the U.S. it takes the piss out of the feeling that Dylan’s subject is pretentious and out dated anchoring the song in post modern realitivism

  11. Pulling mussels is British slang for sex.

    In the early 80s the band Squeeze would also use that term in a song; in fact, it may have even been the name of the song.

    And yes it is mussels as in the shell fish not the part of the human body. Take a look at a steamed mussel in a shell and you’ll see why.

  12. I sang Masterpiece to all 3 of my kids, every night, as each went to bed. Now in their twenties, I get a knowing smile from them when it comes on. Great article, thank you.

  13. I think that “filled with rubble” means that there are antiquities on every corner of Rome, many not even restored or protected. That sense is continued by “ancient footprints are everywhere.” The ancient and the modern live side by side in the Eternal City. You could get tired of it.

    And the Spanish Steps ARE double.

    A slyly funny classic of the “touring is a drag” genre, like “The Ballad of John and Yoko.”

  14. In 1966 Dylan has a motorcycle accident and is obliged to convalesce for several months.In this period he boasts he is reading books no one has ever heard of.He is reading the French Symbolists of the late nineteenth century.In 1968 the BBC series Civilisation is aired on the american television networks attracting an audience of 5 million viewers.In one of the programmes dealing with the Renaissance Sir Kenneth Clark argues artists such as Botticelli gave european thought a new impetus.One way this was done was by the invention of perspective.The eye of the beholder was static.Everything converged on the eye to the vanishing point of infinity which became the Renaissance’s depiction of reality.By the nineteenth century this view was being increasingly challenged by a line of artists from Delacroix to Cezanne.Cezanne held that the eye moved and what you actually saw was a blurred outline and this is reflected in his Mont St.Victoire series where we get the double outline.This for me explains the line “You can almost think you are seeing double”.

    There are other allusions to art masterpieces in the song.The line “Train wheels running through the back of my memory as the daylight hours do recede” could refer to Turner’s “Rain Steam or Speed” or Monet’s scenes of train stations or indeed the Futurists’s depictions of trains in motion.It must be remembered that traditionally scenes from classical antiquity were considered the zenith of High Art and that genre scenes of contemporary life or landscapes were the lowest form of art.In some versions of the song the Brussels verse includes the line”With a picture of a tall oak tree by my side”.The most famous oak tree in european art is the one in Gainsborough’s “Mr. and Mrs.Robert Andrews”.I think Dylan is playfully hinting at what makes for a masterpiece in one era is not considered so in another.Rome historically was the location where english aritocrats went on the Grand Tour and collected classical Italian works for their country estates.There is an amusing scene in Kubrick’s Barry Lyndon where he is being fleeced by an unscrupulous art dealer so he can appear to improve his position in society.

    I think there is an irony here that whenever art claims to be “above” contemporary life more often than not it becomes controlled by it.There was a feeling that art in 1880s Paris had reached a crossroads and this was exemplified in Huysmans’s A Rebours (Against Nature).The hero or anti hero of the novel Des Esseintes shuts himself away in a big house on the outskirts of Paris to contemplate life through his art and literature collection.The work has a “fin de siecle” malaise to it which found a renewed popularity in the 1960s.Marianne Faithful claimed she would sleep with anyone who had read the book.In the closing scene of the 1987 film Withnail and I which was written about life in the 60s you see Marwood put into his suitcase the two Penguin classics David Copperfield and A Rebours.One of the tenets Des Esseintes lives by is that if a work becomes popular with the masses it is to be discarded as its value has diminished.Sometimes a painting achieves a status disproportionate to its artistic merit due to a high auction price or theft.

    In 1972 John Berger produces a 4 part series for television “Ways of Seeing”.The first clip is of him cutting out the face of Venus from Botticelli’s Venus and Mars to give a portrait of the goddess out of context.He is arguing that the camera and modern reproduction techniques have made some images more famous due to advertising.Oddly enough the line “newspaperman eating candy” brings to my own mind Berger’s argument.

    I want to finsh up with the musical line “someday everything is gonna be fine like a rhapsody”.In 1889 Paris held the Exposition Universalle where some international music could be heard for the first time.The sound of the Javanes gamelin leads Debussy to compose “Prelude to an Afternoon with a Faun”.Musical instrument technology was improved and the saxophone is invented.The size of the orchestra was increased enabling Richard Strauss to compose “Also Sprake Zarathustra” with a 100 orcestra members.However I think this reference is more american in origin being George Gershwin’s 1924 “Rhapsody in Blue” combining jazz rhythms with classical music.In 1934 F.Scott Fitzgerald publishes “Tender is the Night” which he considers to be his masterpiece.Unfortunately the book isn’t popular with the Great Depression american public.He is considered a writer associated with the excesses of the Jazz Age as exemplified in The Great Gatsby.The suggestion is that if he had stayed with a more classical tradition the work would have been masterpiece he wanted.The ultimate cleverness of the lyrics is in suggesting a fluidity in art of what actually constitues a masterpiece.

  15. The piano gives a grounded classical feel belied by the song’s subject matter. A nice opening paradox, as from the outset the completion or even starting of the masterpiece is in doubt. It’s like when a little girl says “when I’m a princess”. We know we’re in fantasy land.

    And it’s not clear what is to be the subject of this masterpiece.

    The breadth of the historical landscape set up by Dylan suggests something of earth shattering potential.

    Nonetheless the wonderful rhapsodic imaginings of a fairy tale future might be expected to contrast sharply with

    the solidity of the here and now. And so Dylan sets the scene with the weight of antiquity all around him. But uncertainty swiftly enters through the imagery of seeing double and we start to doubt the firmness of our present and past reality.

    Ambiguity and uncertainty suffuse the song.

    The girl’s from Greece – an even more ancient civilisation than the ancient Roman let alone the Renaissance which is omnipresent in Rome. The Spanish steps are baroque and St. Peter’s itself by Bramante and Michelangelo. 1506-1626 is a dual product of 2 architectural eras (Renaissance [a harking back to antiquity] and Baroque [a theatrical playing with form and light])suggesting that further splittings of time are possible in an infinite regression.

    Or is the blurred vision more a result of geographical dicombobulation?

    We are in Rome, the steps are Spanish, the girl from Greece. The singer himself a Jew from the new land the catholic conquistadores discovered. Our next stop is the colosseum where civilised Rome meets the jungle beasts in a classic Enlightenment v romantic confrontation. You are right to contrast the David of French imperialism with Rousseau’s more Dionysian take on life. Here is another double take between contrasting philosophies – on the one hand man centred reason on the other a belief system centred on earth and nature. America, Dylan’s home, is a technological society struggling to escape its fundamentalist origins. But as a Jew he is a stranger there. Back in Europe he is a double wanderer (dopple ganger?) and as befits a wanderer, and an outsider, he is in real life a troubador. An exotic teller of strange truths, no less than the beasts caged beneath the colosseum.

    The returning Zimmerman is a man twice named. Once for the old country but now for the new, but with a name evocative of a welsh poet, thus evoking yet another fringe European culture in the misty north towards which he will journey on a plane.

    By evoking the train wheels (v american) of his memory, he explicitly mentions memory, thereby cementing the idea of time shift – for what is memory but the personal version of the time lapses referenced in the song in global historical terms. The differences between general and personal time being yet another double seeing. It is appropriate that memory, being a personal vehicle for conjuring the past into the present, utilises the (to Americans) forever 19C train wheels as the vehicle for its evocation whereas his present journey to Brussels is by plane – dirty gondola?

    After BD has built up our sense of the mysterious grandeur of our position, the final “Someday everything is going to be different when I paint my masterpiece”, itself coming after the signally unmysterious grandeur of the candy eating press, seems more forlorn than ever.

    So the song makes clear that the masterpiece is an illusion, and it’s subject matter hinted at but never clarified. But, with all its geographic, cultural, temporal and physical slippages, past and present are equally unknowable.

    Looked at this way the apparently childish hopes expressed in the throwaway suggestion that all will one day be revealed in his masterpiece looks less foolish.

    Or looked at another way, another seeing double, it’s more our present certainties that are foolish.

    Like in the Scorsese film, it’s a mystery inside a paradox inside an enigma – or something like that.

  16. In the show ‘Shadow Kingdom’ Dylan changed
    ‘Got to hurry on back to my hotel room
    Where I’ve got me a date with Botticelli’s niece
    She promised that she’d be right there with me
    When I paint my masterpiece’


    ‘Got to hurry on back to my hotel room
    Gonna wash my clothes, ……………………….?
    Gonna lock the doors and turn my back on the world for a while
    I’ll stay right there, till I paint my masterpiece.’

    No dates anymore for Dylan.

    I stumbled upon the lyrics of a song called ‘The Old Master Painter’, sung by Frank Sinatra among others, and I think Dylan was inspired by this song when he wrote “When I Paint My Masterpiece”.

    The Old Master Painter

    The old master painter from the faraway hills
    Painted the violets and the daffodils
    He put the purple in the twilight haze
    Then did a rainbow for the rainy days
    Dreamed up the murals on the blue summer skies
    Painted the devil in my darling’s eyes
    Captured the dreamer with a thousand thrills
    The old master painter from the faraway hills
    Then came his masterpiece and when he was through
    He smiled down from heaven and he gave me you
    What a beautiful job on that wonderful day
    The old master painter from the hills faraway
    Faraway, faraway

    This ‘painter’ is God, and everything went fine until:
    ‘Painted the devil in my darling’s eyes’
    For some reason or another, God did this.
    But all’s well that ends well,
    God gave him his baby back, with angel eyes I guess.

  17. “Sailin’ round the world in a dirty gondola”
    I’d never thought of the boat since they don’t technically “sail”. To me he was always riding in a hot air balloon, the baskets of which are referred to as a “gondola”. So he’s looking at all of this from above it all.

    Maybe my interpretation is due to my Midwest upbringing (and Bob’s) and our way of pronouncing it. The boat is goon-da-la and the basket is goon-doe-la.

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