Claire Waldoff was a lesbian German chanson and cabaret singer in the 1910s to 1930s. Born in 1884, she moved to Berlin in 1906 to start her acting career, and quickly became famous for her somewhat rowdy, tomboyish, but charming style - she had short hair, wore ties and mens shirts, and would smoke and curse even on stage. In the 1920s she was one of the most famous German entertainers, friends with Marlene Dietrich (who was still obscure at that point), and an out lesbian. She and her long-term girlfriend Olga von Roeder held a lesbian salon and she performed several songs that were either written for male singers or had lesbian and feminist themes, such as “Ach, wie ich die Lena liebe”, “Raus mit den Männern aus dem Reichstag” or - my favourite - "Hannelore", about “the most lovely child of Hallesches Tor”, who is so androgynous that “nobody can tell whether she’s a man or woman”, and who is rumoured to have “both a bridegroom and a bride”.
Her career tanked when the Nazis seized power and made it harder for her to get jobs, and after the war she lost most of her money and her career never recovered. She died in 1957, but is still remembered as one of the biggest stars of the 1920s.
Here’s a good, slightly longer article about her, and many of her songs can be found on YouTube.