"When I Paint My Masterpiece" is a 1971 song written by Bob Dylan. It was first recorded by The Band, who would release their version on Cahoots. Dylan subsequently recorded the song for Bob Dylan's Greatest Hits Vol. II, on which it is segued back-to-back with "Tomorrow is a Long Time". Dylan and The Band performed 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 album Rock of Ages.
In popular culture 
The Band's version of the song was featured in the 2009 film Observe and Report.
Cover versions 
"When I Paint My Masterpiece" was frequently performed by the Grateful Dead throughout their career; the song was sometimes added to setlists alongside several other Dylan songs. Though Dead Guitar/Vocalist Bob Weir sang lead on the song when it was played by the band, Garcia had played the song as early as 1972 with Merl Saunders and John Kahn, both of whom would become members of the Jerry Garcia Band.
Chris Whitley recorded a blues version of the song for his last album, Dislocation Blues, which was released with Jeff Lang in 2005.
Elliott Brood performed "When I Paint My Masterpiece" on CBC Radio 2's "Up Close" program, and include it in some of their concerts.
- ^ Elliott Brood on CBC Radio 2's Up Close