Cashville skyline – an abstract Bob Dylan is up for auction

Consider the Bob Dylan song ‘When I Paint My Masterpiece’, from 1971. It’s usually assumed that this master of metaphor was referring to the great song he believed he could one day write. But was he in fact referring to a more painterly effort?

If he were, Rakewell is glad Dylan didn’t give up the day job. The Minnesotan has won 10 Grammys, an Oscar and the Nobel Prize for Literature, but the Golden Lion for Lifetime Achievement will likely remain out of his grasp. This is despite a recently surfaced painting by the singer-songwriter, dating back to 1968 and now heading to auction for an estimated $100,000. Largely a work of colourful abstraction, it contains a few seemingly random figurative flourishes: a stick-figure with a cowboy hat, an adorable smiley face, some musical notes and, at the centre of the painting, a hulking man-mountain wearing a ‘Viking’ helmet. Dylan had sung about ‘washed-out horns’ in one of his songs only two years earlier – how faithfully he transferred this image on to canvas.

An untitled work by Bob Dylan from 1968. Courtesy RR Auction

In one of his most recent tracks, he sang about how he paints landscapes and nudes. But neither genre is what comes to mind when Rakewell thinks of Dylan’s paintings. Your correspondent is particularly fond of his design for the album sleeve for the Band’s Music from Big Pink (1968), to name one example.

Eagle-eyed Dylan fans will have spotted that the auction is due to take place on the musician’s birthday, 24 May (he will be 83), but however the sale goes, it’s unlikely the man who once plaintively sang ‘No More Auction Block’ will pay it any mind. Having long ago gifted the painting to a fellow resident of Woodstock, he won’t stand to profit from the sale. It seems quaint that Dylan created the work in a time and place – upstate New York in the late ’60s – when people would exchange objects in an informal barter economy rather than buying them with money. But the times, they have a-changed. Having long ago proven himself happy to shill for Chrysler, IBM and even Victoria’s Secret, Dylan’s credo these days is easy to sum up: he not busy being born is busy buying.