- Became interested in comedy as a child in Catholic school, where she learned how to make the nuns laugh to avoid beatings.
- Started singing gigs with her jazz pianist father in nightclubs at age 12.
- In 1987, she emceed the Second March on Washington for Lesbian and Gay Rights.
- Her appearance on The Arsenio Hall Show in 1993 was the first time an out gay comedian appeared on a late night talk show.
- Debut comedy album, Bulldyke in a Chinashop, was released in 1994.
- Released her first jazz album, Play it Cool, in 2001.
- The part of Big Boo on Orange Is The New Black was specifically written for her, after she originally auditioned for a role as a prison guard.
- Lost 50 pounds after being diagnosed with type 2 diabetes in 2015.