- Alan O'Bryant — Backup Vocals
- Merle Watson
- Doc Watson
- Marty Stuart
- T. Michael Coleman
“Listening to the Rain” was written by Don DeVaney. The Osborne Brothers recorded it on 5 March 1970 at Bradley’s Barn in Mount Juliet, Tennessee, for Decca. By then they had been members of the Grand Ole Opry for more than five years. Bobby Osborne sang lead and played mandolin, and Sonny Osborne played banjo and sang harmony with guitarist Dale Sledd in the band’s trio. The rest of the session was Nashville studio players: Ray Edenton on guitar, Leon Rhodes on electric guitar, Hal Rugg on steel, Willie Ackerman on drums and Pig Robbins on piano, with Ronnie Reno on bass. Decca issued it in 1970 on a single with “Midnight Angel” (Decca 32680) and on the album Ru-beeeee.
The song is set on one rainy night. The singer sits at the window, and the house is as cold as the weather because the woman he loves is gone. The storm outside is not as hard on the window glass as his loss is on him. He imagines her in the arms of someone new, and the thought that it may be true is what hurts. Each verse ends with him still wondering where she is as he listens to the rain.
The Osbornes came back to the song in 1986 for Once More (Sugar Hill), a stripped-down acoustic session at Studio 19 in Nashville. Bobby and Sonny sang it with Paul Brewster, with Blaine Sprouse on fiddle and Jimmy D. Brock on bass. A version recorded by Doc and Merle Watson, with parts added by Sam Bush, Marty Stuart and T. Michael Coleman, came out on Home Sweet Home (Sugar Hill, 1998). Special Consensus recorded it for Strong Enough to Bend (Pinecastle, 1996), and Pam Gadd recorded it for The Long Road (Vanguard, 1997). Ronnie Reno, the bassist on the 1970 session, sang it himself on Portfolio (Shell Point, 2002).