"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, released on September 15, 1971. Background Dylan himself first recorded the song at New York's Blue 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 The Bootleg Series Vol. 10: Another Self Portrait (1969–1971). 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. Reception and legacy Douglas Brinkley, while interviewing Dylan for the New York Times in 2020, noted that "When I Paint My Masterpiece" was a song that had grown on him over the years and asked Dylan why he had brought it "back to the forefront of recent concerts". Dylan replied, "It’s grown on me as well. I think this song has something to do with the classical world, something that’s out of reach. Someplace you’d like to be beyond your experience. Something that is so supreme and first rate that you could never come back down from the mountain. That you’ve achieved the unthinkable. That’s what the song tries to say, and you’d have to put it in that context. In saying that though, even if you do paint your masterpiece, what will you do then? Well, obviously you have to paint another masterpiece". Los Lobos' Steve Berlin cited it as his favorite Dylan song in a 2021 Stereogum article, writing, "I love the way he creates such a vivid world in a three-minute song, and as a former constant traveler myself he captures the often delightful feeling of disconnection in a new unfamiliar place,