Remember When Rudy Giuliani Dressed Up in Drag and Let Donald Trump Grope His Fake Breasts?

Image via screengrab.
Image via screengrab.

More than 15 years ago, Donald Trump and Rudy Giuliani recorded what was at the time billed as a “comedic skit” but ultimately turned out to be a chilling public service announcement, as more than ten women can now attest. The main takeaway? Let Donald Trump get too close, and he’ll probably try to grope you.


The short video was recorded for the 2000 Mayor’s Inner Circle—a sort of Harvard Lampoon-styled fundraiser put on by the New York City government and the press that covers it, except generally less funny—and features a cross-dressing Giuliani flirting with Trump in a department store.

Giuliani’s character “Rudia” actually made her debut three years before, much to the consternation of Manhattan’s politicos who felt just uncomfortable enough with his crossdressing to give vaguely homophobic, anonymous quotes to the Times. (“I’m supposed to have a meeting with him in a few days,” a high-ranking City Council official told the Times after his 1997 debut. “I don’t know if I can go through with it.”)

According to the Times, it was the first time a New York mayor appeared in drag in public, though the paper points out Ed Koch once appeared in “in a gold lame stretch bodysuit with a mechanical pigeon on his head,” an unnecessary trend that has continued on, encompassing even Bloomberg in its deeply embarrassing snare.

So by the time Trump’s skit rolled around in 2000, Giuliani’s antics were old news—the Times didn’t even bother reporting on Trump pretending to assault the bewigged mayor.

But the Daily News did:

Trump was among the celebrities making guest appearances in the parody film by Giuliani’s campaign commercial-maker, Adam Goodman. Comedians Jackie Mason, Joan Rivers and Joe Piscopo, New York Yankees owner George Steinbrenner and actor Danny Aiello also appeared.

“What’s wrong with that guy?” became a refrain as the mayor, clad in various costumes, moved about the city-a takeoff on his growing public image and political portrayals of him as vindictive. At one point, Mason was shown at a urinal when Giuliani-in- drag walked into the men’s room and asked for an autograph. “As you can see, this is not a Parker pen in my hand,” Mason said.

Some guests visibly squirmed as Giuliani, dressed in drag as the Marilyn Monroe-like “Rudia” that he first played in the 1997 show, encountered Trump at a department-store perfume counter and tested the products. The tycoon sniffed Rudia’s neck, then plunged his face into her bosom, at which point the mayor shoved Trump away.


Also seated in the uncomfortable audience was Hillary Clinton, dressed in “a gorgeous black gown with velvet cuffs like something out of ‘Zorro,’” fastened by golf-ball-sized cuff links covered with what I figured were rhinestones.”

In the March 13 article, the Daily News reported Clinton, then a political rival of Guiliani’s, smiled through the Trump skit as well as a number of Bill Clinton jokes.


But the ultimate joke was on us, because as a growing number of women have now attested, Trump wasn’t acting.

Just something to keep in mind the next time he tries to pretend a woman was too unattractive for him to sexually assault.

Former Gawker news editor



I was SO HOPING this will make the rounds again. It’s such a perfect storm of misogyny, anti-LGBT imagery, gross sexual innuendo and just plain weirdness that if the sight of it pops gaskets in a just a few of the Trump army, it’ll be well worth it.