When I Paint My Masterpiece

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"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 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 throughout the late 80s and till the band's end. The song was sometimes added to setlists as were several other Dylan songs which were covered even before the Dylan & The Dead Tour was planned. Though Dead Guitar/Vocalist Bob Weir sang lead on the song when it was played by the Grateful Dead, Garcia was playing the song as early as 1972 with Merl Saunders and John Kahn, both who would become members of Jerry Garcia Band. It remained with the Grateful Dead until Jerry Garcia died in 1995, and continued with Bob Weir's group Ratdog.

Chris Whitley recorded a blues version of the song for his last album, Dislocation Blues released with Jeff Lang in 2005.

The Bands cover was featured in the 2009 movie Observe and Report