"When I Paint My Masterpiece" is a 1971 song written by Bob Dylan. It was first released by The Band, who recorded the song for their album Cahoots which was released on September 15, 1971. Dylan himself recorded the song at New York'sBlue Rock Studio when he was backed by Leon Russell and session musicians, including Jesse Ed Davis on lead guitar. The recording sessions lasted from March 16 to 19, 1971, and also saw the recording of the 45 RPM single "Watching the River Flow", released by CBS Records on June 3, 1971. Both songs appeared on Bob Dylan's Greatest Hits Vol. II, released November 17, 1971, with Russell credited as the producer of the two songs. During the March 1971 sessions at Blue Rock Studio, Dylan also recorded a solo version with slightly different lyrics, accompanying himself on piano. This version was released in 2013 on '. Dylan and The Band performed the song together live, in the early hours of January 1, 1972, at a New Year's Eve concert by The Band; a recording was released as a bonus track on the 2001 CD reissue of The Band's live album Rock of Ages. In 2019, five live performances of the song from Dylan's 1975 Rolling Thunder Revue tour were released on the box set '. The Band performed the song at the 1992 Bob Dylan tribute concert. The recording is on the CD of the event.
Dylan's recording is played during the closing credits of the 2013 documentary Tim's Vermeer. The Band's version of the song was featured in the 2009 film Observe and Report. Dylan's recording is played during the closing credits of the 2007 documentary My Kid Could Paint That about child painter Marla Olmstead. Dylan's recording was used over the ending of the 2002 filmComedian. The Band's version of the song was played during the final scene and closing credits of Billions Season 5; Episode 6
Cover versions
"When I Paint My Masterpiece" was frequently performed by the Grateful Dead in concerts starting in 1987; the song was sometimes played alongside several other Dylan songs. Though Grateful Dead vocalist Bob Weir sang lead on the song when it was played by the band, lead singerJerry 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. Tim O'Brien recorded a bluegrass/country version of the song on the album "Oh Boy! O'Boy" with Mark Schatz and Scott Nygaard. Emmylou Harris recorded a version of the song for her album Portraits in 2008. Elliott Smith often played the song live. The bluegrass band Greensky Bluegrass included a live version of the song on their 2010 live album "All Access: Volume 1" recorded at The Riviera Theatre in Three Rivers, MI on Nov. 27, 2009. The song has a regular rotation in their live performances. Blake Mills performed a live solo version of "When I Paint My Masterpiece" on Bob Dylan's iconic Stratocaster to celebrate the 50th anniversary of Dylan's performance at the 1965 Newport Folk Festival. The Backyard Committee included a live version on their album "Plains" released in 2017.
Personnel for studio recording released on ''Cahoots'' by The Band
