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New York Mayor Rudolph Giuliani, dressed in drag as a role in “Victor/Victoria,” sings with Julie Andrews at the New York Hilton in this March 1, 1997 file photo, during an event presented by the Inner Circle. Shocking New Yorkers is difficult, yet Giuliani teetered close to the line when he sauntered on stage wearing a platinum blond wig, a face full of makeup, dainty white gloves and a frilly pink gown filled out in all the right places. Dressing in drag is de rigeuer for New York mayors at the city’s annual Inner Circle dinner - but how it will play with conservative voters in the Republican presidential primaries is unknown. (AP Photo/Joe DeMaria, File)