“Up This Hill and Down” was written by Darrell Statler. The Osborne Brothers recorded it and released it as a single in the mid-1960s, during the stretch when they were among the most prominent acts in bluegrass.
The song uses the rise and fall of a hill road as a figure for a hard, wandering life. The singer travels up this hill and down, through good times and bad, and the lyric measures a life lived on the move.
The song suited the Osborne Brothers’ smooth, modern bluegrass sound and their high lead harmony.
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