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Gaffes on Film: Rudy Giuliani 

No matter your political affiliation, you have to love Rudy Giuliani's ability to mock himself. Starting in 1997 and continuing throughout his mayoral tenure, he was the annual attraction of the Inner Circle mayoral roast, singing musical numbers, dancing the can-can, and appearing in drag, all to gently mirror and mock the
absurdity that is New York City politics.

It's funny, and kind of heartening, to see a politician let his guard down for a bit and go for a joke, especially when the joke's about him, but that doesn't change the hard truth: watching Rudy Giuliani in drag is horrifying. And watching Rudy Giuliani in drag being groped by Donald Trump, who may or may not always be in drag, is enough to drive a voting man straight back into the welcoming arms of 17th century monarchy, where the wigs and powder were expected. Here's a clip of Rudy trotting in 2000:

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