After graduating with a degree in music from Fisk University, Loveless acted in several films and numerous theatre shows during the 1920s and early 1930s.

The latter half of the 1930s saw her move to exclusively vocal performances, including as a part of a harmony group at the 1939 New York World's Fair and in her own musical radio broadcast.

[3] During her time at the university, she joined the Mozart Society and performed as a soprano singer in a 1916 production of The Dream of Gerontius.

[9] After the completion of the musical's run, Loveless left New York and moved to Hollywood to seek other acting opportunities.

[11] After her theatre career, Loveless began working on writing songs and singing opera, joining a "harmony group" named the Chocolate Éclair Family that first became broadly popular after performing at the 1939 New York World's Fair in the Court of Flame building.