Rudy in Leather and Lace

Of all the declared presidential candidates, none has been in costume more than Rudy Giuliani. This picture, representing Giuliani's early work, shows a man struggling to embrace his full aesthetic sensibility. As a U.S. attorney in 1986, Giuliani went "undercover" with Sen. Alfonse D'Amato (right) to show how easy it was to buy crack in New York. Wearing a Hell's Angels black leather vest with patches that read "Dirty Thirty" and "Filthy Few," the future mayor purchased two vials for $20. Apparently, New York crack dealers were sampling their own product. Giuliani's casual-Friday trousers and gold belt buckle make him look more like a man who wants to sell homeowners insurance than a drug addict. And the post-cataract-surgery glasses aren't very menacing, either.
As a candidate for mayor in 1989, Giuliani pounded relentlessly on the incumbent, David Dinkins, for being soft on crime. He was too successful. To soften his image, Giuliani enlisted his then-wife, Donna Hanover Giuliani, a former local news anchor, to narrate an ad attesting to his sensitive side. In the video, Giuliani plays the role of doting father, knocking around at T-ball and launching toy boats in the park with his son. He bottle-feeds the couple's newborn daughter. His choices for showing marital warmth are more avant-garde. He talks into his wife's neck over coffee in the morning and brings into the recovery room what every woman wants after giving birth—a film crew.
Courtesy YouTube.
Much of Giuliani's stage work hails from the Inner Circle charity dinner, an annual New York ritual in which journalists lampoon elected officials. The mayor is permitted a rebuttal and, since the days of John Lindsay in the late '60s, has done so with song and dance and costume. In 1995, just a year into his tenure, Giuliani went back to playing the tough guy in a skit based on the movie Grease. As Giuliani slicks back his hair, his deputy mayor looks on in horror at the audacity of the comb-over. Later the mayor is joined by comedian Jackie Mason, and the two pretend to tussle—or react to bad cannoli from lunch. It's hard to tell.
Photograph by Joe Demaria/Associated Press.
In 1997, Giuliani made an artistic pivot. For the first time he put on women's clothing in public, a trope he would return to throughout his career. (This was also no doubt around the time that Focus on the Family's James Dobson opened a file on him.) Playing Marilyn Monroe in an Inner Circle production with Julie Andrews, Giuliani donned a platinum-blond wig made by RuPaul's wig maker and wore a sequined dress that required three fittings. Hillary Clinton is not the only candidate whose victory will bring us a president who is at ease in a brassiere. "Can you play a woman playing a man playing a woman?" asked Andrews. "Haven't you seen my act?" the mayor shot back. "I already play a Republican playing a Democrat playing a Republican." Later in the show, Giuliani returned in a robe and sang a tune that included the lines: "Once upon a time/ I was a Democrat/ How the press loved that/ But then I grew/ Now I wear a dress/ size 22."
Photograph by Joe Demaria/Associated Press.
By the end of 1997, the mayor was stretching himself as a performer, expanding on his role as a female impersonator from the stage into television. Here he plays Rita Delvecchio's mother in the 1997 Saturday Night Live sketch "Thanksgiving at Rita's." His timing and inflection are off, but his sweet-talk of the police officer shows a deep reservoir of natural talent.

CREDIT: Saturday Night Live, "Thanksgiving at Rita's."
In 1998 for the Inner Circle Gala, Giuliani exchanged his pumps and stockings for claws, fangs, horns, and a long mane of brown hair. For his rendition of "Rudy and the Beast," he arrived in flight on a wire above the stage.
Photograph by Associated Press.
In this 2000 clip, Giuliani shows just how far he has come since his uneven SNL performance as Rita Delvecchio's mother. He has not achieved what the Japanese call onnagata, but look at the fluidity of his sashay as he glides down the department-store aisle. His timing as he delivers his lines has also improved, lending intimacy and immediacy to the performance. Giuliani also shows greater stage awareness. He once famously lectured a caller to his radio show about the man's fixation with weasels, but he stays in character throughout this skit, unfazed by the furry woodland creature nesting quietly at the back of Donald Trump's hair.
Courtesy YouTube.
Back in leather, Giuliani finally accessorized like a professional as he plays the bike-riding, chain-wielding bad boy in another Inner Circle Gala spoof of the musical Grease.
Photograph by Arnaldo Magniani/Getty Images.
The Don in a thong. In his last Inner Circle performance, Giuliani returned to his strength in 2001, playing the cross-dressing leader of an organized-crime family who participates in a kick line with the Rockettes. Joined in the skit by several members of the cast of The Sopranos, Giuliani stuffed cotton in his mouth to play Don Giuliani in a spoof of The Godfather. Candidates need to be comfortable in their skin. Giuliani may be the first to prove that he's comfortable in a woman's skin, too—as well as in her clothing.
Photograph by Joe DeMaria/Associated Press.