Hedwig and the Angry Inch

Musical about a transgender rock star.

In the 2001 film Hedwig (left) was played by actor John Cameron Mitchell and Yitzhak (right) by actress Miriam Shor. 

Famous Sopranists

Sopranists are male singers able to reach the vocal range of a female soprano.

Examples include...

Thomas Otten

Vitas

Klaus Nomi

Arve Henriksen

Antony & The Johnsons

Lead singer Antony Hegarty identifies as transgender, but as a constant state rather than transitioning from one gender to another. In personality and appearance, he seems to embody a feminine vulnerability and creative energy. In interviews, he seems very comfortable with this state of gender deviance, and suggests transgendered people simply have a different 'spirit' to people who identify as strongly male or female. This spirit fuels many of his songs, where he is able to sing from the points of view of people from many genders.

"I made a choice to, sort of, really spell it out for people, especially since I’m not someone that is transitioned to—towards anything, really. I’m just sort of in a process of embracing myself as a transgender person and presenting myself, you know, as I am…"
http://curate.tumblr.com/post/338805207/an-interview-with-antony-hegarty