British powerhouse singer Annie Lennox got onstage at the 1984 Grammy Awards and performed “Sweet Dreams (Are Made of This)” with her then-band the Eurythmics in full drag.
“I remember enjoying very much being in another persona,” she said in an interview. “That was interesting. That was like a piece of performance art. Apart from performing, I actually inhabited this male persona for a few hours.”
In 2011, the germ put on a cringe-inducing high school after-school performance dressed as a greasy douchebag named “Jo Calderone” at the MTV Video Music Awards at Nokia Theatre in L.A.