“Friend of the Devil” has words by Robert Hunter and music credited to Jerry Garcia and John “Marmaduke” Dawson, the singer of the New Riders of the Purple Sage. Hunter told the story more than once. He had the song more or less written when he brought it to a New Riders rehearsal, and Dawson and guitarist David Nelson helped him smooth out some rough chord changes. Over coffee, Dawson told him that one repeated line, “it looks like water but it tastes like wine,” fell flat. In his 2006 online journal Hunter credited Dawson with the replacement, “a friend of the devil is a friend of mine,” which also gave the song its title. In a 1978 interview he had told it the other way, with himself finding the line. They recorded the song that night. The next morning Hunter found Garcia, who had not been at the rehearsal, already working it out on pedal steel, and the Grateful Dead took it over, to the New Riders’ dismay.
The Dead first played it in concert in March 1970, at the Capitol Theatre in Port Chester, New York. The studio recording was made at Wally Heider’s studio in San Francisco between August and September 1970 and became the second track of American Beauty, which Warner Bros. released that November. David Grisman, who had recently moved to California, played mandolin on it. He later recalled that Garcia had asked him to play on the record after they ran into each other at a baseball game in Fairfax.
The narrator is running from almost everyone. He lights out from Reno with twenty hounds on his trail and borrows twenty dollars from the devil. He spends a night in a cave in Utah, and the devil catches him at the levee and takes the money back. Then come two reasons to cry: sweet Anne Marie and the prospect of prison, with the sheriff closing in. In the last verse he has a wife in Chino and another in Cherokee, and the first says she has his child, “but it don’t look like me.” The chorus only hopes he gets home before daylight and some sleep. Where he ends up is never told.
The DeadDisc discography counts more recorded cover versions of “Friend of the Devil” than of any other Grateful Dead song, and bluegrass bands took it up early. The group Country Store recorded it on 5 February 1974 for their Rebel album, with Jimmy Gaudreau on mandolin. Garcia sang it again with Grisman on Jerry Garcia & David Grisman (Acoustic Disc, 1991), recorded at Grisman’s Dawg Studios in Mill Valley with Joe Craven and Jim Kerwin. Larry Rice sang lead on the version by Rice, Rice, Hillman & Pedersen (Rounder, 1999). Rob Ickes and Trey Hensley included it on The Country Blues (Compass, 2016).