"When I Paint My Masterpiece" is a 1971 song written by Bob Dylan. It was first released by The Band, who covered the song on their album Cahoots. Dylan himself recorded the song in the March 1971 sessions that were produced by Leon Russell. From these sessions came the "Watching the River Flow" single and this track. Both appeared later in the year on Bob Dylan's Greatest Hits Vol. II. (An outtake of the song, from the same March sessions, 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.

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 film Comedian.

"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 singer Jerry 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.

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