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.

