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(Credit: Far Out / Alamy)


The song that connects Bob Dylan, The Band, and the Grateful Dead


Together, Bob Dylan, The Band, and the Grateful Dead have almost no direct ties. Individually, of course, they have some of the strongest bonds in all of music. That’s mainly thanks to Dylan: at different times in history, both The Band and the Dead acted as the legendary singer-songwriter’s backing band. The Band filled the role before they officially became their own entity in the mid-1960s, while the Dead took on the role for Dylan and the Dead tour throughout the summer of 1987. The Band and The Dead only played one concert together on June 21st, 1984.

Even after they had separated themselves from his leadership, The Band still continued to collaborate with Dylan. Most famously, Dylan’s post-motorcycle accident recuperation coincided with The Band’s initial gathering of songs for their debut album, Music From Big Pink, and the resulting Basement Tapes have become some of the most legendary home recordings of all time.

Those recordings would provide some initial songs for The Band to take on during their first recordings sessions, including ‘I Shall Be Released’, ‘Tears of Rage’, and ‘This Wheel’s On Fire’. But Robbie Robertson began to assert himself as the group’s songwriter, and wished to give The Band their own artistic bona fides separate from their connection to Dylan. For their next two albums, The Band consciously had no Dylan songs in their repertoire.

But 1971’s Cahoots found the band softening their desire to distance themselves from Dylan. They had kept close, even as they worked separately, and Dylan had recorded a song during the early months of 1971 that Robertson and his bandmates took a liking to. Dylan had slowed his recording process by the early ’70s and wasn’t planning on releasing an album that year, so The Band took on ‘When I Paint My Masterpiece’ based on the recording that Dylan had already laid down.

When Cahoots was released in September of 1971, Dylan was compiling the material to be featured on Bob Dylan’s Greatest Hits Vol. II. Originally, Dylan wanted to include some of the Basement Tapes recordings, but Columbia Records head Clive Davis rejected them, leading Dylan to re-record some of the songs and include previous studio outtakes to flesh out the album’s tracklisting. One of those outtakes was a version of ‘When I Paint My Masterpiece’, which saw the light of day just two months after The Band released their own version.

The close release didn’t seem to bother either party: neither Dylan nor The Band released ‘When I Paint My Masterpiece’ as a single, and the artists actually performed the song live together at The Band’s 1971 New Year’s Eve show in New York City. Although it occasionally floated around Dylan’s and The Band’s respective live shows, the song mostly laid dormant until Dylan hooked up with the Dead for their summer 1987 tour.

Both Bob Weir and Jerry Garcia expressed a fondness for ‘Masterpiece’, and the song was one of many Dylan songs that stayed in the Dead’s setlists after their tour together ended. The Dead’s version of ‘Masterpiece’ alternated between an uptempo jaunt and a haunting ballad, with the song becoming more sombre and introspective as the group neared its end. Both Weir and Garcia had sung the song with their solo projects, and ‘Masterpiece’ eventually became a first-set staple for the Dead during their final decade together.

So well-loved was the song that it found a spot in the setlist of the Grateful Dead’s final show in Chicago during 1995, with Dylan continuing to perform the song in recent years as his Never Ending Tour continues to roll on.

Check out all three versions of ‘When I Paint My Masterpiece’ down below.