“Crying My Heart Out Over You” is credited to Lester Flatt, Earl Scruggs, Carl Butler, and Earl Sherry and was first released by Flatt and Scruggs in 1959, peaking at No. 21 on the country chart in 1960. The Flatt & Scruggs reading is solidly inside the early Foggy Mountain Boys’ sound — brisk tempo, tight Foggy-Mountain banjo, and Flatt’s clear baritone — but the song did not become widely covered until two decades later.
In December 1981, Ricky Skaggs cut it as the third single from his Epic album Waitin’ for the Sun to Shine. The Skaggs version reached No. 1 on the country chart in March 1982 — his first of eleven country No. 1s — and effectively reset the song’s place in the canon. Skaggs’s arrangement keeps the bluegrass instrumental palette but slows the tempo and adds the country-radio production sheen that defined the early-1980s neo-traditional country movement he was helping to lead.
The lyric is a straightforward heartbreak text, and its long shadow over country and bluegrass has more to do with what it represents — a bluegrass-derived song crossing the country chart at No. 1 in 1982 — than with any single arresting verse. It remains a frequent vocal feature for bluegrass-leaning country singers and a comfortable jam-friendly singer’s number.
