Here's a real outsider oddity: an autobiographical album of original songs and spoken-word narration from an elderly woman recounting her life as a pioneering female Jewish cantor. This 1997 release apparently came with her book of the same name, "Trusting The Song That Sings Within." Looks like you can still buy it.
Dora B. Krakower's singing isn't as horrific as, say, Mrs. Miller or Leona Anderson, but the spare piano accompaniment certainly doesn't hide her voice or pretty it up with lush orchestrations. You get to hear it in all it's operatic glory.
Dora B. Krakower: "I'm Pussyfooting Around My Age"
Dora B. Krakower: "I Keep On Trusting Me/She Calls Herself A Cantor?"
So if you want to hear an older woman singing about her "drooping derriere," look no further then the first song. The second tune contains the memorable lyric: "Shall I recant from the chant/ like a toady syncophant," which she pronounces "psycho-phant."