- Waylon Jennings — Lead Vocals
- Billy Joe Walker Jr. — Guitar
- Reggie Young — Guitar
- Dann Huff — Guitar
- Tony Joe White — Guitar
- Mark O'Connor — Fiddle
- Jerry Douglas — Dobro
- Leland Sklar — Bass
- David Hungate — Bass
- Curtis Young — Backup Vocals
- Rick Marotta — drums
- John Barlow Jarvis — piano
- Steve Schaffer — Synclavier
“Grapes on the Vine” is credited to Steve Gillette and Charles John Quarto. Gillette has written that it began as a poem by Quarto which he set to music when the two started collaborating in the early 1980s; they went on to write several dozen songs together, and Quarto brought him into the studios at Jack’s Tracks in Nashville. Gillette has said he was struck by how Quarto brought the central figure to life: a man who leaves comfort behind to see the wide world, who has some street wisdom but also an overview, and who “sees beyond.”
The song is sung about that wanderer rather than by him. The narrator describes a man you might have passed on the road, going somewhere or nowhere, a constant orphan of the world who lives on apples from orchards and dies from grapes on the vine. He turns up in big-city winters and in the suburbs, in Pittsburgh at Christmas and in Buffalo in June, knowing the back roads between them, and he dreams of a railroad life. The last verse, set on Route 22 again, has him looking strong and trying to seem like somebody’s friend while puzzled by the rest of the world.
Waylon Jennings recorded the song on 14 June 1988 in Nashville, with Jimmy Bowen producing, for his MCA album Full Circle, released in September 1988. Gillette recorded it himself on his 1989 Compass Rose album American Songwriter and again in 1992 on The Ways of the World (produced by Jim Rooney, with Stuart Duncan on fiddle). Tony Rice and the Rice Brothers included it on their 1989 Rounder album The Rice Brothers (Rounder 0256), and Wildfire recorded it for Rattle of the Chains (Pinecastle PRC 1148, 2005). Gillette also names Ronny Cox and Bill & Bonnie Hearne among those who have recorded it.