“Up This Hill and Down” is credited on the Osborne Brothers’ Decca records to Richard D. Staedtler. Sonny and Bobby Osborne recorded it on the morning of 7 October 1965 at the Columbia Recording Studio on 16th Avenue South in Nashville, at a session produced by Harry Silverstein. Sonny played banjo, Bobby mandolin and Dale Sledd guitar, and all three sang. Ray Edenton added a second guitar, with Lightnin’ Chance on bass, Willie Ackerman on drums and Hargus “Pig” Robbins on piano. The same session produced “Memories,” “Big Spike Hammer,” “I Know What It Means to Be Lonesome” and “In the Pines.”
Decca paired the song with “Memories” on a single (Decca 31886) at the turn of 1966, with “Up This Hill and Down” on the B-side. In June 1966 it became the title track of the LP Up This Hill and Down (DL 4767). MCA later reissued it as the flip side of the Osbornes’ “Rocky Top.” Other bands picked it up: Roby Huffman and the Bluegrass Cutups recorded it in 1971 and the Teays Valley Boys in 1973. Buck White and the Down Home Folks played it on Live in Japan around 1980, and Larry Stephenson and Mark Newton opened Live at Mr. B’s (1988) with it.
The lyric is shaped like a blues. Each verse states a line, repeats it, and answers with a short tag. Climbing the same hill up and down stands for a road that never ends. The singer works from five in the morning until midnight and has no life to show for it. He complains that a woman will drive a man out of his mind, though he admits he likes the pain. He dreams of a day when money will spare him hard work, plans to talk to his woman on Saturday and to the Lord on Sunday, and ends up convinced that every kind of trouble follows him around.
