Song of the Day 4/11: Bob Dylan, “When I Paint My Masterpiece”

This song ran through my head after a visit to the Vermeer exhibition at the Rijksmuseum in Amsterdam. The Dutch master was only 43 when he died in 1675 in Delft, and outside of official records very little is known of his life.

He remained admired but obscure until the mid-18th century. He was popularized in the mid-19th century, and he’s been a sensation ever since. This exhibit, which collected 28 of the three dozen or so surviving paintings attributed to him (a couple are disputed), sold out its 450,000 tickets in three days. (The museum has put together an online tour, narrated by Stephen Fry, for those who missed out). It’s hard to say which one is his masterpiece.

As a visual artist, Bob Dylan has been more prolific — an exhibition of his artwork last year gathered more than 200 items, most of them more accomplished than the one he dashed off for the cover of his double LP, “Self Portrait,” in 1970. That was the year before he wrote and recorded this tune at a recording session with Leon Russell.

In Russell’s telling, he wanted to see Dylan’s writing process, so he wrangled a session. With his Shelter People backing him, Russell played Dylan this wordless tune and watched while Dylan paced the studio and scribbled phrases as he listened.

In a sense, he’s still writing them — lines have changed almost as often as the song has been recorded. In the original session, first released on “Bob Dylan’s Greatest Hits Volume II,” Dylan had a date with Botticelli’s niece.

When Dylan recorded it again days later, a solo piano version that wasn’t officially released until 2013 on his bootleg series’ “Another Self-Portrait,” she had become a “pretty little girl from Greece,” as she was in the Band’s cover, the song’s first official release.

It quickly became a concert staple for the Band, the Grateful Dead and Dylan himself. Douglas Brinkley asked Dylan about the song in a 2020 interview, and Dylan analyzed it almost as if someone else had created it.

“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 sentiment echoes what Dylan often said led him to release the critically savaged “Self Portrait,” in an attempt to escape the “Voice of His Generation” microscope the press and public had put him under.

To demonstrate that the song might not be finished yet, here’s how it sounded when he recorded it as the opening number of his 2021 concert film, “Shadow Kingdom.” Among other changes, Bob is no longer going back to his room for a date. Now that he’s 80, he’s just going to wash his clothes.