Rudy Giuliani's Cross-Dressing Antics Back in Spotlight as He Runs for President

[Omaha Steve]

Source: Associated Press

Rudy Giuliani's Cross-Dressing Antics Back in Spotlight as He Runs for President

04-14-2007 2:30 AM
By SARA KUGLER, Associated Press Writer

NEW YORK (Associated Press) -- It is difficult to shock New Yorkers, yet Rudy Giuliani teetered close to the line when he sauntered onto a 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.

His appearance at an annual political roast was exactly 10 years ago, and at the time, the idea of the tough-talking mayor in a busty ball gown raised eyebrows but was mostly accepted as a good joke _ adhering to an unwritten rule for the shenanigans that take place at the roast, known as the Inner Circle dinner.


New York Mayor Rudolph Giuliani, right, 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)


Shortly after winning re-election that year, Giuliani took his feminine side to a national audience. While hosting "Saturday Night Live," he appeared in one skit as a bosomy, gray-haired Italian grandmother in lipstick and a flowered housedress, with stockings pulled halfway up his calves.

Now that Giuliani is running for the Republican presidential nomination, experts and political observers are wondering whether those well-photographed and widely documented performances _ and others _ could damage his campaign. Some say conservatives won't get the joke and will be turned off by what they see as yet another peek at Giuliani's exotic, big-city liberal side.

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[Ian David]

1. He actually looks much better as a woman. n/t

[iamjoy]

2. Help Needed - My Idea

can some one with video editing talent take these pics of Rudy in drag and put them in a video to post on YouTube set to either

"Lola"
"Dude Looks Like A Lady"
"Sweet Transvestite"
"I Feel Pretty" (a swipe back for the John Edwards video)

I dunno, or is this insulting to tranvestites?

[DuaneBidoux]

3. Will voters care? Yes for the rethugs, no for us. How ironic.

[BlueStater]

4. Republicans like big manly men like this one: