NEW YORK – 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.
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.
Political observers say many voters associate a macho demeanor with Giuliani's post-Sept. 11 image as a strong national leader in a time of crisis — an image that could lose its power if dressed in stockings and dancing the cancan.
Yes, there was another year when he wore fishnets and did high kicks with the Rockettes.
"People think of him as a leader and a tough guy, and he has this image as somebody who tamed the city of New York and made the trains run on time, and seeing him dressed up like a girl would run contrary to all of those things," said political science professor Neal Thigpen of Francis Marion University in South Carolina.
South Carolina has one of the nation's earliest presidential primaries next year, and as the first Southern contest, it could set the stage for the region.
With conservative voters largely dominating presidential primaries, some experts say the footage of Giuliani cavorting about in women's wear could significantly damage his chances there and throughout the South. The images are already showing up on the Internet, including a mock campaign commercial on the popular video-trading site YouTube.
"You get out in more sophisticated places of the country, where they know Giuliani and they like him and they know about some of his antics, it's not going to be any surprise, but down here where they've never seen that kind of thing, it could do him some damage," Thigpen said.
But others say the gender-bending gags won't matter.
In Nevada, another state with an early caucus, Republicans would be unfazed by the image of Giuliani in women's clothing, said Heidi Smith, chairwoman of the Republican Party in Washoe County.
Giuliani impressed Reno citizens in a campaign appearance there last month that included a trip to Costco during which he mingled with shoppers, posing for photographs and signing autographs.
"That meant more than seeing him in drag," Smith said. "If he wants to wear a dress, who cares?"
Giuliani's first drag appearance, in 1997, featured a breathy Marilyn Monroe impression that was followed by various other female alter-egos over the years, including one that shared a scene with Donald Trump, who groped Giuliani and buried his head between the mayoral breasts.
His other Inner Circle characters included a 1950s greaser on a motorcycle, the Lion King and the Beauty's beast.
His most famous appearance from 10 years ago is likely to be remembered this weekend when Mayor Michael Bloomberg gets into costume to dance and sing for the same charity event, as New York mayors have done for decades. David Dinkins once donned full cowboy regalia and entered the ballroom on a horse; Ed Koch wore a suit of glittering gold; and Bloomberg has ridden a mule and pretended to smoke pot.
In 1997, the New York media had fun for a few days with Giuliani's first cross-dressing experiment — the Village Voice printed a favorable review by real drag queens — but it didn't appear to hurt him politically.
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.
Still, a poison-pen mailer or e-mail could easily imply a connection, observers say.
"I'm imagining the negative ads — they could use this as sort of an oblique reference to all of those positions," said Clemson University political scientist Dave Woodard.
Southern Baptist Convention official Richard Land said gay issues represent just one area of the problems religious conservatives have with Giuliani.
"There are so many dealbreakers for Giuliani, it's difficult to know where to start," he said.
Throughout his eight years in City Hall, Giuliani supported laws that protected gays against harassment, marched in gay pride parades, welcomed the Olympic-style Gay Games to New York City and, after his second marriage broke up, lived with two friends who happened to be a gay couple.
He does not support gay marriage, but he does not see the need to ban it with a constitutional amendment. And in a 1994 cover story with The Advocate, a national gay magazine, he condemned Pat Buchanan's speech at the Republican National Convention two years earlier during which the failed presidential candidate declared a "cultural war" against homosexuality, radical feminists, abortion rights supporters and other "liberals."
The speech, Giuliani said, "tried to narrow rather than to broaden the Republican Party. There is no reason why the party shouldn't appeal to gays and lesbians in the same way it does to all Americans."
Over the years, Giuliani's relationship with gays has not been exactly cozy — he was often heckled while marching in the city's annual gay pride parade.
Asked this month about his theatrical past, Giuliani told Fox News that it shows voters another side of him.
"I think what they'll find out about me is I enjoy having fun. I mean, I really enjoy those Inner Circles. I made them fun, and I enjoyed them," he said. "And so you're going to get a couple of things people can interpret different ways, I guess."