Posted on 04/14/2007 10:14:39 AM PDT by Spiff
Giuliani's cross-dressing antics back in spotlight
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."
This guy’s personal life is a train wreck. Were he to be the nominee, the MSM would kill him.


The urban and suburban professionals Rudy appeals to will find his self-deprecating humor to be refreshing. The yahoos in the stix will not understand it, but they were rendered irrelevant in 2006 and will be more so next year.
Rudy can easily turn this lemon into lemonade by going on Oprah or Letterman, letting the photos be put out there, having a good laugh over it and pointing out how many people benefitted by the charitable fund-raising his antics facilitated. If he can find a baby who was cured and now lives a productive life because of Rudy's ability to poke a little fun at himself, so much the better.
The only place these photos hurt Rudy Giuliani is in the imaginations of the anti-Rudy crowd. It is one more example of their bad political judgment.
No way. This is the Presidency of the United States we are talking about here. The leader of the free world. Nobody wants a cross-dresser in the White House. Once may be a good nature gag, twice is a big problem. He's done. That is a humiliating photo that will hang around his neck like a millstone.
Wrong.
Some of the antics and groups he still aligns himself with show that it’s more than antics, it’s ENDORSEMENT.
Classic Northeastern elitism...where the border stops in Greenwich Village.
Southerners ain't that cloistered.
Exacty. You couple these pictures with the fact he lived with some gay men and you begin to wonder what else is going to come out.
This statement qualifies as the "Delusion of the Week".
“The cross-dressing stuff helps Rudy more than it hurts him.”
Yeah, you keep telling yourself that.
Your statement here makes the rest of us wonder how you dress when you go out...
If Republican opponents in the primaries decide to give his cross dressing a pass in the primaries do you think the Democrats will let it pass in the general election?
No need to answer since I already know they would trash him with it.
I think that pretty well sums up your candidate's view of the people who were very recently regarded as the heart and soul of the Republican Party.
For all of Guiliani’s faults, this particular non-issue is one of the stupidest things I’ve ever seen used in order to smear a candidate. Anyone who is interested in the reason why he was dressed as a woman can learn the facts surrounding those charity events, skits, Saturday Night Live performance...yata yata
I know I’ve said it before and I’m sure flames will be thrown my way by those who believe the crap being spread around that Guiliani is a “drag queen”. People who say that lose all of my respect.
I’m not sure which newspaper it was ( British I think) that interviewed one of the queers Rooty lived with. He said Rooty gave him a kiss on the cheek every morning when he left for work.
I’m sure that will be used in captions of those drag pictures.
I just don’t know if I could do it. Going to the voting booth, ready to mark his name instead of Hilary’s or Obama’s or whoever’s - and seeing his Tootsie picture in my brain. A sense of humor is valuable. But there is something wrong with that picture. I just don’t know if I could vote for him.
Oh please, John Garfield owned an entire wardrobe of pink taffeta gowns that he would wear on holidays. President Taft had a fetish for high heels. LBJ often wore women’s panties and a bra. Its been rumored that Warren Harding had both male and female genetalia and used to conduct vivisection experiments on kittens in the oval office!
/sarcasm off
I doubt the terrorists will care “why” he dressed as a woman. They will simply use the photos to recruit. I bet recruitment will go through the roof.
“THAT’S their leader? BWAHAHHA!! Where do I sign?”
The only ones who believe that have drunk too much Roody-Aide.
Rudy’s habits ping!
—as one who has gone to Halloween parties in drag, years ago, padded and completely disguised except for my 5’11” height, I agree with you—— but the Demotraitors will use this against Guilaini regionally if he is the candidate-—
The "yahoos in the stix" (otherwise known as red-state voters in flyover country who constitute the base of the GOP) are sick of slicks like you talking down to them.
If Rudy had done it once, it would be forgivable. But he's done it on several occasions. He seems to have some sort of a cross-dressing fetish, and seems to enjoy it a little too much. I, and most people I know, won't vote for a transvestite.
Or people who use their own statements as “evidence” to support their positions.
The question is how voters will ultimately react to Giuliani’s willingness, some might even say *eagerness* to get involved with gags which include cross-dressing (Milton Berle was notorious for this but I don’t recall anybody questioning his masculinity), the political risk is exactly what has already been emphasized, i.e., images of Rudy in drag subconsciously remind people of his liberal views on homosexual ‘rights’, on abortion, on gender issues, his own marital escapades, which eventually lead to his firmly stated positions on other issues like guns, economics, etc.
The cross-dressing is just a side-show (some might say a freak show), there are much more substantial issues that Rudy is 100 percent wrong about that will end up derailing his presidential aspirations.
The only way Rudy is going to the White House is by invitation, or by lining up for the weekend tour outside the gates. Sorry Rudyphiles, that’s just the way it is.
Do you believe conservatives watch those twits? I thought those programs were for hte liberals. Oops, I forgot this is Rudy Judy we are talking about.
LOL!
I love watching the Rudy haters pull every scrap they can to try to knock him down. Not realizing that each time they do it they look kookier and kookier and it only helps Rudy among the rational voters.
You think that terrorists will be able to recruit more Islamic extremists because of these old pictures? I don’t think that’s on their top ten list of why they want to kill us.
Terrorists readily don women’s clothing as a disguise. I’ve also read that Arab men put on women’s robes to sneak into the women’s quarters of houses for assignations. So I doubt they’ll be shocked at all. You’re the one who has a problem with a longstanding theatrical practice.
Also, contrary to this article, I don’t recall New Yorkers being shocked by any of these appearances.
No...
It's goofball LIBERALS like Kerry in the "bunny suit", Dukakis with the oversized helmet on in the tank turret, and RINO-rudy in his various cross-dressing outfits that have the bad political judgement.
“The yahoos in the stix will not understand it, but they were rendered irrelevant in 2006 and will be more so next year.”
"Habits"? Good Lord, aren't you aware of when these events took place either? If that's a habit, then I'm a habitual drunk because over ten years ago I got a bit tipsy a couple of times at two weddings and one big shindig.
Maybe she is concerned about his bringing the Teflon Don down.
Well, after all, he “knows people”. That makes him an expert.
*Snicker*
Anti guiliani posters, turning FR into a cesspool of negativity.
And yet they are all so cheap, it takes three weeks or more to raise a lousy 70,000 dollars.
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.
Conservatives can't get a joke. Conservatives are stupid and humorless prigs.
From Some Like it hot, Toosie, Bosom Buddies, I Was a Male War Bride, and so many numerous roles, being in drag has been received as comedy from time immemorial.
Both William Shatner and James Spader appeared in drag this year without and negative criticism.
I imagine the laughter at the very top of Democrat party hierarchy will be unrestrained.
Not only is everything we believe about Conservatives reinforced, but that the unattractive Conservative handicap of a lack of a sense of humor may damage the only candidate who may beat us.
Who says "real" Conservatives and the Left can't make common cause.
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. "That meant more than seeing him in drag," Smith said. "If he wants to wear a dress, who cares?"
Damn, I feel so culturally insensitive. I'm a city slicker too - maybe I need to eat more tofu and less red meat?



Wooo-hooo!
BRAVO!! As I’ve read these ridiculous threads I’ve wondered how these same posters would respond if it was THEIR chosen candidate that was being smeared by something as ridiculous as this. I bet most, if not all of them, would be singing a different tune. They’d find their sense of humor real quick.
You know what? Call me back when you find footage of him trying to deep-throat a microphone.
Both William Shatner and James Spader appeared in drag this year without and negative criticism.
Oh I'm sorry. I forgot the highest office in the land was the same thing as a sitcom or funny movie, and that William Shatner and James Spader were running for President.
And yet they are all so cheap, it takes three weeks or more to raise a lousy 70,000 dollars.
Could be that the normal posters here are so sick of the liberal bent of the Rudymaniacs that they are not contributing. I mean, why support another leftist site?
Yeah, Central Scrotumizer, it's the (liberal) intelligentsia you're a member of that are the ONLY "rational" voters.
That's liberal-speak, just like it's entirely "reasonable" and "sensible" for gun-grabbing maggots like RINO-rudy to sh*t on our 2nd Amendment rights.
And speaking of "kooky", it's one of you RINOmites that posted (in this thread) that RINO-rudy's many cross-dressing episodes would actually HELP him in his run for the presidency.
You RINOphiles are amazing.
I’ll be damned if I can see why living in a city, too damned dumb to unstop a toilet, makes these people feel superior.
In my decades as a hardware salesman and small engine technician, the one thing that impressed me most about N.E. urban transplants was their total lack of knowledge, beyond whatever little niche they actually had experience in.
How they can be condescending to folks who actually know, and do things, is beyond me.
And it seems that it is his only choice of costume. If it were only a matter of play acting, why does he only choose women's outfits. The Rudy machine would surely have other pictures or video clips out there if they did in fact exist.
Rudy did an ok job for NYC but his record on major issues nails that he is not a conservative by any means. What's sad is that a conservative site can't contain the discussion on issues this early in the pre-election positioning. To demand that we adhere to a candidate selected by the mass media is the height of stupidity...
Disclaimer: Opinions posted on Free Republic are those of the individual posters and do not necessarily represent the opinion of Free Republic or its management. All materials posted herein are protected by copyright law and the exemption for fair use of copyrighted works.