“Forty Years of Trouble” was written by Troy Spencer, a mid-Atlantic banjo picker and songwriter who died on November 16, 1998. Spencer’s songs — plain-spoken, hard-edged, built around single character studies in the older hard-country mould — were adopted by traditional bluegrass acts across the mid-Atlantic and upper-South circuits; “Cardboard Mansion,” another of his pieces, was recorded by both Danny Paisley and the Lonesome River Band. The song was first released by Bob Paisley and the Southern Grass, the West Virginia traditional-bluegrass act that was among the closest listeners to Spencer’s writing during his lifetime.
The song was recorded by Aubrey Haynie on his 1997 album Doin’ My Time, with one of the deepest session-band lineups of the late-1990s bluegrass studio scene: Haynie on fiddle and mandolin, Bryan Sutton on guitar, Béla Fleck on banjo, Jerry Douglas on dobro, Dennis Crouch on bass, with Ricky Skaggs and Gene Johnson handling baritone and tenor harmony respectively. The Haynie reading is the version most contemporary bluegrass pickers know first.
The lyric is a long-prison-sentence narrative — the narrator counting forty years inside, one disappointment after another, the woman who waited for him long since gone — in the hard-luck tradition that runs from “In the Pines” through “Long Black Veil.” The song is a comfortable slow vocal piece in G or A and remains a frequent call in traditional bluegrass sets where the singer wants a brooding character study.