Grateful Dead – When I Paint My Masterpiece (Live in 1987)

“When I Paint My Masterpiece” is one of the many classic songs that Bob Dylan bestowed upon the world. The Grateful Dead started doing a cover of it in June 1987, and played it close to 150 times before Jerry Garcia died in 1995. Garcia also covered it with the Jerry Garcia Band, but I always preferred the Grateful Dead version. When Jerry adds high harmony during the chorus, it gives me chills. So many great lines in this song – “someday, everything’s going to be different”, “newspaper men eating candy”, and “train wheels running through the back of my memory” to name a few.

Here’s the Grateful Dead playing it an Anaheim Stadium in 1987, a little more than a month after they first debuted the song.