Rudy Giuliani in drag

“Rudy Giuliani in a dress: Will voters care?” MSNBC

A poll shortly afterward found his approval rating at an all-time high of 67 percent, and a majority of city voters said they enjoyed the gag. He won re-election later that year.

Perhaps New Yorkers, who are overwhelmingly Democrats by a margin of five to one, appreciated one particular line during the 1997 show, which was a spoof of the musical comedy “Victor/Victoria,” in which a woman pretends to be a man pretending to be a woman.

“I already play a Republican playing a Democrat playing a Republican,” Giuliani quipped.

For conservatives who already are leery of backing Giuliani because of his support for abortion rights and other positions on social issues, the feminine clothing may also remind them of his support of gays while mayor — despite the fact that the majority of cross-dressers are not gay.

“The Long Tail of Candidate Searches,” Time

Meanwhile, Rudy Giuliani, the Republican front-runner according to the latest polls, was the subject of the fewest searches. This probably has no bearing on his popularity; it’s most likely due to the fact that people can’t spell “Giuliani.” The most common Giuliani searches focus on his stance on taxes and the war. Beyond that, however, there’s an odd obsession with finding images of “Rudy Giuliani in Drag,” perhaps fueled by some circulating photos from a 2000 political roast. It’s just weird.

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