“Chalk Up Another One” is credited to H. Winston and Wilmer Neal — names that appear on the RCA paperwork and almost nowhere else in the songwriter literature. Whoever they were, they wrote a honky-tonk heartache lyric: the singer keeps score of his own disappointments, chalking up one more lost love like a mark on a tally board, a jukebox conceit closer to the 1950s country chart than to the older mountain repertoire.
The song entered bluegrass through its first recording. On November 16, 1954, at RCA Victor’s Nashville studio, Jimmy Martin and the Osborne Brothers cut it at their only session together for the label — Martin on guitar and lead vocal, Bobby Osborne on mandolin and tenor, Sonny Osborne on banjo and baritone, with Red Taylor on fiddle and Cedric Rainwater on bass. RCA released it in February 1955, backed with “I Pulled a Boo Boo.” The Martin–Osbornes partnership lasted barely a year, which makes the handful of sides it left behind — this one, “20/20 Vision,” “Save It! Save It!” — a compact document of two major careers at the moment before they diverged.
The song’s place in the working repertoire owes much to the Bluegrass Album Band, whose 1981 recording on The Bluegrass Album put it in front of a new generation of pickers; it has been a jam-session staple since.