The 30 Greatest Bob Dylan Songs: #27 “When I Paint My Masterpiece”

“Oh, the streets of Rome…” Those five words transport Dylan fans into a world of coded imagery. We’ve all climbed down the Spanish stairs with him, hurrying on back to our hotel rooms, where we’ve got ourselves a date with a pretty little girl from Greece.

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Okay, maybe that’s too gender-specific. But who among us hasn’t spent time in the Coliseum, dodging lions and wastin’ time?

Thing is, you can imagine all the events described in “Masterpiece” as actually being part of a routine day in in Dylan’s life — but to the rest of us, they become personal metaphors.

There’s a lot to love about this song — the sense of fun in the vocal, the ever-so-tasty chord change from major to minor that makes the bridge so delightful each time you hear it, and the fact that Bob took it upon himself to rhyme “muscles/mussels” with Brussels” (somebody had to do it.) Also, the idea of Bob Dylan, who has certainly written his share of masterpieces, (painting, well, that’s a whole other ball of wax — and isn’t it interesting how Dylan’s artwork resembles Woody Guthries’?) being perpetually on the look out for the one song that will stand above all the rest is a great image for the aspiring artist. Don’t look back, keep going.

“When I Paint My Masterpiece” first appeared on 1971’s Greatest Hits Vol. II, so it sat in some pretty good company. If Wikipedia is to be believed (and when have they ever lied?), that album was originally going to include an entire side of unreleased material.

The Band covered it on their 1971 album Cahoots, and promptly made it their own (it’s practically synonymous with Levon Helms’ voice). The Grateful Dead made it a set list staple in the 1990s. Even Elliott Smith gave it a go. But as the saying goes, nobody sings Dylan like Dylan.


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  1. But the question that I would like to have blind boy grunt himself answer: Is Renaldo and Clara to, in some significant way, be seen as his masterpiece? If so, it is certainly masked like Bob in his opening song. We are all left seeing double!!

  2. Watching – well, taking a mini-break, because … – the Scorcese documentary about “Rolling Thunder Revue” that was shown on Netflix in 2019 (10 years or so after the last person commented) has an extended clip of Bob singing this song…. I was 20 or so when Dylan was an int’l sensation, so he was pretty “formative”/significant to me, but I somehow NEVER heard this song. Amazing. And Google brought me here, and the analysis/vibe/etc. here is 100% in keeping with the great music…. just like the sparkle off a jewel. I.e., there wouldn’t be these fine words if there hadn’t been (in this case) that fine song, but the words somehow amp up what you get from the music alone.


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