Here’s an early painting done by Dylan as an album cover for The Band, Music of the Big Pink in 1968. The second darker version ( same painting) is the cover of the remastered 2020 release. More details in comments.

‘Dylan offered to sing on the album, but ultimately realized it was important for the Band to make their own statement. Instead, Dylan signified his presence by contributing a cover painting. Barney Hoskyns has written that it is significant the painting depicts six musicians. The cover of Music From Big Pink was intended to establish the group as having a different outlook from the psychedelic culture of 1968. Photographer Elliott Landy flew to Toronto to photograph the assembled Danko, Manuel, Robertson, and Hudson families on the Danko chicken farm. A photo was inserted of Diamond and Nell Helm, who lived in Arkansas. The photo appeared on the cover with the caption “Next of Kin”. The overall design of the sleeve is by Milton Glaser (who also did the poster that was packed with the 1967 Bob Dylan’s Greatest Hits.
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