“Pain in My Heart” came out of the Lonesome Pine Fiddlers’ first recording session. The band, led by bass player Ezra Cline, had been on WHIS radio in Bluefield, West Virginia, on and off since 1938, and in 1949 it took on two young musicians: Bobby Osborne on guitar and Larry Richardson on banjo. With fiddler Ray Morgan and Cline, they made their first records, four songs for Cozy Records, a small label from Davis, West Virginia; “Pain in My Heart” was cut at the WHIS studio in March 1950. The record credits Osborne and Richardson as the writers. Osborne sang the verses and the tenor in the chorus, and Richardson took the lead line in the chorus. Cozy issued it in October 1950 with another Osborne–Richardson song, “Lonesome, Sad and Blue,” on the other side, and Coral reissued the coupling in April 1952.
The singer has loved the woman from the first and asks her to look in his eyes and say she loves him too. The chorus pairs the pain in his heart with the blues on his mind and asks how she can be his while she carries another man’s name. In the last verse he begs her not to say goodbye.
Flatt & Scruggs picked the song up within months. They recorded it on 20 October 1950 at radio station WDAE in Tampa, Florida, with Lester Flatt singing lead and Curly Seckler tenor, Earl Scruggs on banjo, Seckler on mandolin, Benny Sims on fiddle and Jody Rainwater on bass. Mercury released it on 15 March 1951, backed with “Take Me in a Lifeboat.” In November 1952 Bobby’s younger brother Sonny Osborne recorded it at the Gateway studio in Cincinnati for a Kentucky label single issued in 1953.
Del McCoury recorded it on 12 April 1976 at Track Recorders in Silver Spring, Maryland, for Our Kind of Grass (Rebel, 1978). On 22 September 1980, at 1750 Arch Studios in Berkeley, the Bluegrass Album Band cut it for The Bluegrass Album (Rounder, 1981), with Tony Rice singing lead, Doyle Lawson tenor, J.D. Crowe baritone and Bobby Hicks bass. The Lonesome Pine Fiddlers entered the International Bluegrass Music Hall of Fame in 2009, and at the ceremony Bobby Osborne, Melvin Goins and Paul Williams sang “Pain in My Heart” in the closing performance.