For the Inner Circle gala—that bizarro NYC event where Giuliani dressed in drag—Bloomberg booked the cast of Hair for a skit entitled Mair. He'd better be wearing a bra. Bonus: He could even burn it at the end!
A celebration of insidery old boys' clubs, the Inner Circle "is composed exclusively of the men covering politics in city newspapers ... an outgrowth of the Association of City Hall Reporters, which began giving stunt dinners about eight years ago," according to a 1923 New York Times article on Inner Circle's website. Since then, the schtick hasn't changed much, although modern contexts have perhaps changed the relevance of seeing our male politicians in lipstick. Anyway, Bloomberg has so far done skits with the casts of Chicago, Spamalot, and Mary Poppins, and he hasn't worn drag yet, but hold fast to dreams, you know? [P6] [Pic via Getty. Makeup simulation merely a suggestion for Bloomberg's delicate coloring. Call me if you want a consult, Blooms.]