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Penny Sterling, wearing earrings, glasses and a blue scarf

PENNY STERLING hasn't always been Penny, but she has always been funny. She received her BA in Drama from Ithaca College in 1981, and has performed on stages and in comedy clubs across New York and in Canada--as an actor, stand-up comedian, and as a member of several improvisational troupes. Penny is an accomplished storyteller in more than one way: She's Emmy-nominated television producer/director and the former head writer of The North Pole Times website.

Penny spent the first half-century of her life living as a man, getting married and divorced, raising children, and trying to ignore the part of her soul that kept telling her "this is not who you are!" In April of 2014 she finally admitted to herself that she was transgender, and 18 months later she began living her authentic life, much to the surprise of most of her family and friends. Penny encouraged them to ask questions, and her responses became the framework for her show Spy in the House of Men: A One Woman Show with Balls, which earned her critical and audience acclaim around the country. 

While still performing Spy, Penny is also performing Parents & Children, Husbands & Wives: It's all Relatives, a collaborative evening of song and story with musicians Mike & Mel Muscarella, of Violet Mary, (coming to Cleveland in July 2019), and writing two new shows: SHMILF LIFE (her take on dating [or lack thereof] as an older transgender woman debuting in Rochester in September 2019), and Children are Designed to be Raised by  Idiots  (stories and assurances about the best, hardest, dumbest job ever).


Penny lives in Rochester, NY, with her two youngest children (when they're home from college) and her cat, Betty (who has shown no inclination towards secondary education).

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