“Tomorrow I’ll Be Gone” is credited to Wilma Lee Cooper, who recorded with her husband, the fiddler Stoney Cooper, as Wilma Lee and Stoney Cooper. Bill Monroe and his Blue Grass Boys recorded it on 30 January 1959 at the Bradley Film & Recording Studio in Nashville, with Jack Cooke on guitar, Buddy Pennington on banjo, Bobby Hicks and Charles Smith on fiddles and Bessie Lee Mauldin on bass. Decca released it on 19 October 1959 as a single, backed with Monroe’s own “Dark as the Night, Blue as the Day,” cut at the same session.
The singer has been left for someone new and feels lost, like a grain of sand or a ship thrown about in a storm. The chorus turns to the one who left: their eyes will open one day to find they lost the game they played so lightly, and that the new love has flown off like a bird. By then the singer will be gone. In the last verse the leaving is likened to autumn leaves that do not come back, and the heart is in pieces.
Wilma Lee Cooper’s own recording came twenty years after Monroe’s. She made it in 1979 at KA Recording and Sound Corp. in Roanoke, Virginia, with Carol Lee Cooper singing harmony, Gene Wooten on dobro, Stan Brown on banjo and Craig Duncan on fiddle, for A Daisy a Day on the Leather label; Rebel reissued the album in 1983. By then the song had been taken up by others. Hazel Dickens and Alice Gerrard recorded it on 14 October 1972 at Urban Recordings in Bethesda, Maryland, with Mike Seeger on mandolin and fiddle, Tracy Schwarz on fiddle and Lamar Grier on banjo, for their Rounder LP Hazel & Alice (1973).
The Johnson Mountain Boys cut it on 20 October 1982 at Bias Recording Co. in Springfield, Virginia, and opened their album Working Close (Rounder, 1983) with it; Dudley Connell played guitar, Richard Underwood banjo, David McLaughlin mandolin, Eddie Stubbs fiddle and Larry Robbins bass. Big Country Bluegrass made it the title track of a 2000 album on Hay Holler, and Dailey & Vincent recorded it in Nashville for Brothers of the Highway (Rounder, 2013), with Jamie Dailey singing lead.