Sometimes Being Rudy is a Drag

Rudy Giuliani in Drag 1997

“Rudia” is his drag name.

With a penchant for platinum blonde wigs, dainty white opera gloves, and frilly pink gowns cut low to show off her ample bosom, this drag queen with the falsetto singing voice was a well-known figure in N.Y.C nightlife at the end of the last century.

You may know him better as America’s Mayor. Or Donald Trump’s failed flunky.

I knew him as the Queen of New York.

During the years I lived in that city it was hard to forget having a tough-as-nails former prosecutor mayor who repeatedly dressed in drag.

It was not without its irony.

No one was more aggressive in cracking down hard in closing clubs and cabarets. Rudy brought back a Prohibition-era cabaret law that banned dancing in bars without a license for it. By the 1960s, it was only used against gay bars, and that era ended after the June 27, 1969 raid on the Stonewall Inn. But Giuliani resurrected it. Ordering club raids, his obsessive scrutiny of clubs, franticly looking for reasons to fine them or shut them down changed the nightlife of N.Y.

For someone hell-bent on wanting to take the fun out of “Fun City,” Rudia had plenty of fun herself.

Take another look pal, this babe may be a boy

Years before Rudy fell under Donald Trump’s hypnotic sway, the tables were turned.

Donnie was once caught in the seductive charms of “Rudia.”

Making the rounds online is the 2000 video when Rudolph Giuliani was still mayor of N.Y.C. and Donald Trump was a celebrity businessman.

The clip was first brought back into the public eye in 2016 during the presidential election when Steven Colbert unearthed an old video sketch that featured Trump motor-boating Guilinai, who was dressed in drag.

The skit — which was recorded for the Inner Circle Show, an annual event put on by media to poke fun at the N.Y.C. mayor and other local political figures — included Trump flirting with Giuliani as he wore a wig and dress reprising his drag alter ego Rudia.

“I moved on her hard. I did try and fuck her.”

Rudy “Rudia” Giuliani and her many charms

“You know, you’re really beautiful,” Trump, said to “Rudia” as she tried on perfume at a department store counter.   Donald popped some Tic-Tacs just in case he starts to kiss her.

After Trump got closer to smell “Rudia’s” neck, the then-mayor sprayed perfume on her chest area. Overcome with desire,  (“ I’m automatically attracted to beautiful”) Trump may not have grabbed her by the pussy, but he went in for a whiff, pushing his face in between the mayoral fake breasts.

A shocked “Rudia” reacts by calling Trump a “dirty boy” and slapping him. As “Rudia” walks away, Trump looks at the camera and retorts:  “Well, you can’t say I didn’t try.”

Later he would explain to Billie Bush about his failed attempt with the gorgeous “Rudia.”

“I moved on her like a bitch. But I couldn’t get there, And she was married. Then all of a sudden she’s now got the big phony tits and everything.”

But Rudy’s penchant for drag goes back further.

Dressed to the nines Rudy sauntered onto the stage at the New York Hilton in March 1997 in his signature blonde wig, full makeup, and pink gown, as “”Rudia”a nightclub singer. He sang in falsetto and shared a tango with “”Victor/ Victoria’s” Julie Andrews–dressed as a man

“Rudia,”  made her first public appearance in 1997 at a N.Y.C. charity dinner, and the media described the spectators as “thunderstruck” at their “transvestite” mayor.

The NY Times Reported on March 3, 1997

But no one was fully prepared for the sight of New York City’s brawling Mayor as he tottered onto the New York Hilton stage Saturday night in high heels, a full-figured spangled pink gown, a platinum-blond wig and several pounds of makeup. This is a man, after all, who has to pay media consultants to find his sensitive side.

But in his newfound incarnation as Rudia, a transvestite nightclub singer, the Mayor even sang a falsetto version of ”Happy Birthday, Mr. President” — a la Marilyn Monroe — and waved daintily at the crowd of thunderstruck spectators.”

The audience of journalists, public officials and lobbyists greeted Rudia with a huge outburst of applause and hoots of sustained laughter, but when it became clear that the Mayor was actually going to deliver a sustained performance in the outfit, members of the crowd seemed torn between being amused and being appalled.

When he pulled a huge cigar out of his sock, and later began dancing an intimate tango with the star of ”Victor/Victoria,” Julie Andrews (dressed as a man), several well-known audience members could be seen with their foreheads in their hands, open-mouthed.

But it was the image of Mr. Giuliani in mascara and lipstick that most people carried out of the room with them.

That same 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.

National Review July 25, 2006

But today politics can be a drag.

Today this New Yorker better stay away from the south.

Forget the criminal probe in Georgia, Rudy Giuliani best steer clear of Tennessee and their anti-drag performance laws.

“Rudia” the bewigged bedazzled former prosecutor could find herself behind bars.



  1. Great stuff. Maybe Rudi was auditioning for FBI Director?

    Liked by 1 person

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