Heartbreak is the engine that drives a huge chunk of the bluegrass repertoire. Bill Monroe wrote some of the saddest songs ever put to a mandolin, and the Stanley Brothers built a whole sound around lonesome. These 25 songs are the ones that come up at jams, on stage, and in late-night kitchen sessions wherever pickers gather. Some are old mountain ballads like “In the Pines” and “Bury Me Beneath the Willow.” Others came straight from the first generation of bluegrass, like “Blue Moon of Kentucky” and “Little Cabin Home on the Hill.” A few crossed over from country and folk, like “Tennessee Waltz” and “Fox on the Run,” and pickers claimed them as their own.

Use this list as a starting point for a heartbreak set, or just to fill gaps in what you already know. Each song’s page on Picker’s Guide has chord charts, lyrics, recordings, and song history.