When I Paint My Masterpiece

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“When I Paint My Masterpiece”
album track by Bob Dylan
Album Bob Dylan's Greatest Hits Vol. II
Released 1971
Length 3:22
Label Columbia
Writer Bob Dylan
Bob Dylan's Greatest Hits Vol. II track listing
"Tomorrow is a Long Time"
(17)
When I Paint My Masterpiece
(18)
"I Shall Be Released"
(19)


"When I Paint My Masterpiece" is a song written by Bob Dylan and first featured on the Bob Dylan's Greatest Hits Vol. II compilation in 1971. The song is segued back-to-back with "Tomorrow is a Long Time" (which is the the song right before it on the album). Even though there is applause at the beginning of the song, it is in fact a studio recording. The audience noise is only fade-in from the previous song.

"When I Paint My Masterpiece" was also recorded by The Band, who would release their version first on 1971's Cahoots album. Dylan and the Band would perform the song together at a New Year's Eve concert later that year, a recording of which was released as a bonus track on the 2001 CD reissue of the Band's live Rock of Ages album.

"When I Paint My Masterpiece" was also played by the Grateful Dead in various stadiums around the US from around 1987, probably in part because of that year's Dylan and the Dead tour, which then brought this song into their body of work along with numerous other Dylan covers. The song remained with the Grateful Dead till their end, and continued with Bob Weir's group Ratdog.