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Dapper Lunatic

I'm looking for a couple of depressing songs that feature a female singer with a really sultry voice accompanied by a piano and/or a sax. Anything come to mind? Can anyone point me in the right direction?

Hygienic Dabbler

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Check out some late Billie Holiday, or late Ella Fitzgerald. Also check out these below:

Etta James
Peggy Lee
Rosemary Clooney

Just check out their songs. Different artists do a range of different songs...not everything is gonna be gloomy!

Hot Rot's Prince

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Gloomy Sunday by Lady Day, Kozmic Blues by Janis Joplin, and Sinnerman by Nina Simone are my go-to depressing songs.

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Ella Fitzgerald is really good. Anita O'Day is also amazing, but she isn't incredibly depressing.
Billie Holiday's songs are always about her man doing something to her, so she's a good choice.

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