Prison songs run deep in bluegrass, and most pickers know the big ones — “Folsom Prison Blues,” “Long Black Veil,” “Twenty One Years.” These eighteen sit a step behind those, but they hold up just as well. Some are old murder ballads like “Knoxville Girl” and “Tom Dooley” that drifted into the bluegrass repertoire. Others are bluegrass originals about doing time, like “Stone Walls and Steel Bars” and “My Main Trial is Yet to Come.” A few are newer, including Billy Strings’ “Dust in a Baggie.” What ties them together is the same thing that ties any good prison song together. Regret, a hard sentence, and the long view from inside.

Use this as a jumping-off point for your next jam or a quiet evening of woodshedding. Each song’s page on Picker’s Guide has chord charts, lyrics, recordings, and song history. Start with whichever title pulls at you and follow the trail from there.