This song is about Billie Holiday and her turbulent life. Holiday was nicknamed "Lady Day" or "Lady" and her autobiography was titled Lady Sings The Blues.
Suggestion credit: Katie - Woodland Hills, CA
Some of the lyrics refer to specific songs Holiday recorded. "No Regrets" is the title to one of Holiday's songs, and "Stretched out like a poplar tree" comes from the lyric "Strange fruit hanging from the poplar trees" from her song "Strange Fruit."