First recorded (as “Loveless Love”) by Noble Sissle & His Sizzling Syncopaters (1921).
Also recorded (as “Loveless Love”) by W.C. Handy’s Memphis Blues Band (1921), James P. Johnson (1921), Alberta Hunter (1923).
Other popular versions (as “Careless Love”) by Bessie Smith (US #5 1925), T. Texas Tyler (1946), The Ravens (1949), Fats Domino (1951), Ray Charles (1962).
From the wiki: “‘Careless Love’ is a traditional song of obscure origins. The song lyrics change from version to version, but usually speak of the heartbreak brought on by ‘careless love’; most often a girl’s lament for having loved unwisely, worrying what her mother will say when she returns home, ‘wearing her apron high’ (i. e. pregnant).
“The song was one of the best-known pieces in the repertory of the Buddy Bolden band in New Orleans, Louisiana, at the very start of the 20th century, but it is thought that the first recording of ‘Loveless Love/Careless Love’ was made by Noble Sissle & His Sizzling Syncopaters at a New York City recording session in January, 1921.
“Bessie Smith recorded the first popular version of ‘Careless Love’ in 1925. The song has since gone on to become a jazz and blues standard. Hundreds more recordings Smith’s nationally-popular verson, in blues, jazz, folk, country, and pop styles. T. Texas Tyler recorded a Texas Swing version in 1946 for 4-Star records. ‘Careless Love’ would shortly thereafter enter the repertoire of the ‘King of Western Swing’, Bob Wills & His Texas Playboys.
“Fats Domino made a recording of it in 1951, releasing it as the B-side of ‘Rockin’ Chair’. Ray Charles’ recorded ‘Careless Love’ for his landmark 1962 album, Modern Sounds in Country and Western Music.”
W.C. Handy & His Memphis Blues Band, “Loveless Love” (1921):
James P. Johnson, “Loveless Love” piano roll (1921):
Alberta Hunter, “Loveless Love” (1923):
Bessie Smith, “Careless Love Blues” (1925):
T. Texas Tyler, “Careless Love” (1946):
The Ravens, “Careless Love” (1949):
Fats Domino, “Careless Love” (1951):
Ray Charles, “Careless Love” (1962):