First recorded by Lester Flatt, Earl Scruggs & The Foggy Mountain Boys (C&W #21 1960).
Hit version by Ricky Skaggs (C&W #1 1982).
From the wiki: “‘Crying My Heart Out Over You’ was co-written by Lester Flatt and Earl Scruggs, and originally recorded in 1960 by Flatt & Scruggs, whose version peaked at #21. It was covered in 1982 by Ricky Skaggs, his third Country hit and the first of eleven #1 hits for him on the Country chart.”
Ricky Skaggs, “Crying My Heart Out Over You” (1982):