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Bottom left: Mary Lou Williams at the piano, "one of the very few capable female jazz musicians". Yeah, right. The 2011 film The Girls in the Band finally documents the many, many women jazz artists and swing bands in the 1920s, 30s, and 40s, up through the present day (link is to a Youtube trailer, sorry for ads).
Bottom right: Billy Holiday singing Fine and Mellow. The caption doesn't say, but I think that's her own orchestra.