It’s got all the makings of a classic love song: A young man, so in love with his girl, goes to a local jewelry store to make that certain large purchase. And that’s where this one sours. You’re listening to Teddy Grace with Betty and Dupree, recorded in 1939. It’s based on a true story from 1929 Atlanta, where Frank Dupree attempted to steal the ring in question, killing a police officer.
The Grateful Dead played this song, but lyricist Robert Hunter penned his own version, “Dupree’s Diamond Blues”, first performed by the group in 1969. Jerry Garcia called him “the band member who doesn’t come out on stage with us.” He was inducted, with the rest of the Dead, into the Rock and Roll Hall of Fame in 1994.