In this interview with Bob Dylan published June 12, 2020, there is a discussion of his 1971 song “When I Paint My Masterpiece”.
“Out of all your compositions, “When I Paint My Masterpiece” has grown on me over the years. What made you bring it back to the forefront of recent concerts?
It’s grown on me as well. I think this song has something to do with the classical world, something that’s out of reach. Someplace you’d like to be beyond your experience. Something that is so supreme and first rate that you could never come back down from the mountain. That you’ve achieved the unthinkable. That’s what the song tries to say, and you’d have to put it in that context. In saying that though, even if you do paint your masterpiece, what will you do then? Well, obviously you have to paint another masterpiece. So it could become some kind of never ending cycle, a trap of some kind. The song doesn’t say that though.”
I have always thought it was a great song and maybe his best song from the 1970s. The first version to be released was The Band’s on Cahoots (released 9/15/71). Dylan’s version was on Greatest Hits, Vol. II (released 11/17/71).
Dylan has changed them right from the beginning. The Band version has “a date with a pretty little girl from Greece”. Dylan’s version has “a date with Botticelli’s niece”. The live version by Dylan and the Band from December 1971 which is on the expanded Rock of Ages has the line as “pretty little girl from Greece”. This was after he had recorded it with “Botticelli’s niece”. The official lyrics have “Botticelli’s niece”. I saw him perform most recently in November 2019 and there were other changes. I don’t recall what they were but I didn’t think they were improvements.
There are covers, too.