Giuliani's Cross-Dressing Antics Debated

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) (Joe Demaria - AP)

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.