"Crying My Heart Out Over You" is a song written by Lester Flatt, Earl Scruggs, Carl Butler, and Earl Sherry and was originally recorded by Flatt & Scruggs, which peaked at #21 on the country chart,in 1960.In 1982, the song was recorded by Ricky Skaggs. "Crying My Heart Out Over You" was Ricky Skaggs third country hit and the first of eleven number one hits on the country chart. The single stayed at number one for one week and spent a total of thirteen weeks on the country chart.