Did you hear the one about the plot to sneak estrogen into Hitler’s carrots? It sounds like the setup for a joke, but the Allies really tried this one out.
A study at the time by the U.S. Office of Strategic Services, a precursor to the CIA, claimed that on the gender spectrum, Adolf Hitler fell notably near the middle—"close to the male-female line," wrote the OSS’s director of research and development, Stanley Lovell. The Allies thought if they could just tip him over the line into "female" territory, he would lose his hold on Germany and the war would be won.
Sources differ on whether the hope was that a more feminized Hitler would be less aggressive, and thus, less inclined to commit mass genocide, or that if he lost his facial hair and grew breasts he simply wouldn't have the confidence or charisma to allow him to serve as an effectively malevolent dictator.
We know that didn’t happen, but the reasons why are murky. Read about the scheme to feminize Hitler at mental_floss.