Libby Holman, a Jewish girl from Cincinnati, arrives in Manhattan in 1925 and begins to make a name for herself as a torch singer, trading on her racially-ambiguous skin tone and deep voice at a time when white hipsters think the height of cool can be found in Harlem. Libby and friends like Tallulah Bankhead sojourned uptown not just to listen to Black music, but also to explore their bisexuality. Through mutual co-star Clifton Webb, Libby meets Jeanne Eagels – one of the greatest actresses of her generation, and a high-profile casualty of Roaring 20s debauchery.

(00:00) Torch Singer, Accused Murderess, Bisexual

(09:05) A Confederate Jew

(17:53) Sex Appeal to Burn

(25:59) “Coon Shouting” and Libby’s Racial Ambiguity

(41:32) Blackface on Broadway with “Moanin’ Low”

(49:10) Sex Tourism in Harlem

(58:28) Jeanne Eagels