How the World Fell Head Over Heels for RuPaul

Image may contain Clothing Apparel Coat Suit Overcoat Human Person Sleeve and Preston Bailey
RuPaul, wearing a custom-made suit, has been filming a scripted series he cocreated for Netflix, AJ and the Queen, due later this year. Sittings Editor: Madeline Weeks.Photographed by Annie Leibovitz, Vogue, May 2019

IT’S A DEWY, not-quite-spring morning in March, and I’m lingering outside a soundstage on the Warner Bros. lot where RuPaul will be photographed for Vogue, waiting to behold him in full drag.

This studio is where Judy Garland filmed A Star Is Born, and it is now where RuPaul is shooting AJ and the Queen, a forthcoming Netflix series he created with Michael Patrick King, the head writer and executive producer of Sex and the City. (Ru is a down-on-her-luck drag queen named Ruby, traveling cross-country with an eleven-year-old orphan named AJ, played by the young actor Izzy G.) I’ve already asked to observe the pre-shoot transformation—who on God’s green earth wouldn’t?—and received a no from Team Ru that was polite but ironclad, as though I’d requested the nuclear code: “Ru’s glam process has been kept very private throughout his career.” So I’ve settled for a glimpse of the final butterfly.

I’m not sure which Ru to expect. Will he be an outsize Barbie-superhero who fell to Earth, à la RuPaul’s Drag Race, or a throwback incarnation of a nineties runway glamazon? Golf carts full of crew members cruise by, and I scan them for signs of a blond bouffant. Then, with no warning, a honey-smooth, startlingly assertive voice rings out from within the soundstage: “The titties aren’t gonna get any higher than this!

I make a beeline inside. Most of the studio consists of a nightclub set, which itself gets a constant makeover: Because AJ and the Queen is a road story, its drag numbers are set in different clubs across the country. Right now, however, all bodies are hovering around a small cloth backdrop. Annie Leibovitz is standing on top of an apple crate, peering through her camera lens.

If you approach Mother Ru from the side, as I did, the first thing you will need to process is the eyelashes. The skull-to-eyelash ratio is so physiologically improbable that it’s a good 30 seconds before I realize that Ru is not dressed as any of his familiar alter egos. Rather, he’s a modern facsimile of Queen Elizabeth I, clothed in a billowing gold-brocade skirt, a corset, and a halo of red dreadlocks.

He knows which side is his good side. He knows how the light is hitting. He knows to lower the lashes to half-mast and let them hover there as the camera clicks. And when, after a while, Leibovitz suggests he remove his headpiece, he knows to object.

“It becomes something else without the piece,” Ru says, gesturing to the rest of his puffy-sleeved costume. “The piece sells everything else.”

“Your hair becomes a crown,” Leibovitz says gently. The exchange goes on for two minutes. Finally, RuPaul puts his (combat boot–clad) foot down. Remove the piece, and he is no longer in character. “Everything here is overdone,” he says, motioning again to his look, and then to the surroundings. “The only natural thing about any of this is the light.”

It occurs to me that RuPaul has just offered up a definition of camp. (“The essence of camp is its love of the unnatural: of artifice and exaggeration,” Susan Sontag wrote in “Notes on ‘Camp.’ ”) More remarkably, he and Leibovitz have just unwittingly re-created one of the photographer’s most memorable shoots.

You see, twelve years ago, when Leibovitz took official portraits of Queen Elizabeth II in full regalia at Buckingham Palace, one of America’s most well-known portrait photographers asked England’s longest-reigning monarch to remove her “crown.” (It was a tiara.) A BBC film crew captured the exchange.

Leibovitz: “It will look better—less dressy—because the garter robe is so. . . .”

Queen Elizabeth II: “Less dressy? What do you think this is?”

The queen of the United Kingdom did not want to take off her headpiece. And here in beautiful downtown Burbank, neither does the Queen of Drag.

WHEN RUPAUL FIRST sashayed into the national consciousness, in 1992, with the release of his single “Supermodel (You Better Work),” there was nobody like him in mainstream culture. There were androgynous pop stars (David Bowie, Prince, even Cher), but none who bent gender nearly as far. And there had been a few drag characters in major films—Some Like It Hot, Tootsie—but RuPaul’s use of drag was new. “Drag was not the goal,” explains Lady Bunny, the drag artist and founder of Wigstock, the drag extravaganza held in New York’s Tompkins Square Park every year from 1985 to 2001. “Escaping something was the goal. Ru did drag with the nerve to say, I’m pretty.”

And yet, if you were a thirteen-year-old girl in suburbia when RuPaul hit, as I was, and mesmerized by the swagger, as I was, chances are good you spent zero seconds unpacking the politics of his pop-stardom. It was only when I rewatched the “Supermodel” video last month that I fully appreciated its air of satire—how it takes the diva antics and the fantasy of the fashion world to a subversive extreme. In one scene, RuPaul flirts with a camera while draped upside down on the hood of a taxi. In another, he frolics in the fountain next to the Plaza hotel in a bodysuit and a boa. When he rattles off the names of supermodels (“Linda, Naomi, Christy”), in what I now recognize is a parody of Madonna’s “Vogue” (“Greta Garbo and Monroe, Dietrich and DiMaggio”), the covers of spoof magazines flash across the screen. Among the titles: Swish, Ms. Thing, and Drague.

TWO DAYS AFTER his Vogue shoot, I meet RuPaul for coffee at a hotel in West Hollywood. He arrives looking nothing like Britain’s queen: a six-foot-four string bean in black jeans, a black turtleneck, black ankle boots, a pale trench coat, a vintage Gucci belt, and a black biker’s cap. At 58, he is ageless. If he is wearing any makeup, it’s not enough to cover his smattering of freckles.

We settle into a corner table. When a waiter arrives, RuPaul orders “regulah cawfee,” in an exaggerated New York accent. “You’re gonna make the coffee hot,” he adds, in non-question form. “You don’t want to do an Americano, do you?” the waiter replies. RuPaul starts to decline, then changes tack: “Let’s do an Americano. You know, the universe offers clues, and if you’re listening, you just say: Yes, that’s what I want.”

It is difficult to describe the aura of civilian RuPaul. Michelle Visage, a close friend, Drag Race judge, and cohost of RuPaul’s podcast, uses the word otherworldly. So does Mally Roncal, the makeup mogul, adding that he is a “fierce angel.” Isaac Mizrahi says he is “almost like a prophet,” one who is “constantly flying a little higher than everybody else.” Michael Patrick King likens him to “an Egyptian cat”—but also “an encyclopedia,” and I know exactly what he means. Spend a morning with Ru and you will believe it possible that he is an alien-anthropologist sent to conduct an ethnography of the American subspecies. In telling me his life story, he will cite—and this is an extremely abridged list—Bewitched, Coty cosmetics, Yardley cosmetics, the history of wheat-pasting concert flyers, Dolly Parton, Clash of the Titans, the films of John Waters, the technology of early camcorders, The Wizard of Oz, Issa Rae’s Insecure, Maureen Dowd’s Are Men Necessary? and Steamboat Willie.

Indeed, a conversation with RuPaul can leave you with the sensation that there is infinite wisdom to be wrung out of just about everything, provided you shed your earthly hang-ups and get hip to the glorious freedom of category collapse. Only then will you see that the advertising slogan “Do you have any Grey Poupon?” is also shorthand for a certain kind of code-switching. That the supermodel moment of the 1990s was a residual effect of the feminist movement of the ’60s and ’70s. That pop stars are not merely pop stars but reflections of the secret selves of the consumer.

“I am a drag queen who understands camp and who understands how to comment on what’s happening within the Matrix,” RuPaul tells me. He means the culture at large and the masses who consume it. “My job, our job as drag queens, has always been to remind you that this outfit you’re wearing, or this label you put on yourself, is just a label. Drag queens are the shamans or the witch doctors or even the court jesters—to remind you what is really real.”

“In my career, I’ve been able to show certain angles. I’ve been able to paint on a face and edit what I presented.” Hair: Curtis Foreman; Makeup: David Petruschin.Photographed by Annie Leibovitz, Vogue, May 2019

RuPaul Andre Charles was born in San Diego in 1960. His mother, Ernestine Fontinette, who went by Toni, worked in the registrar’s office at San Diego City College. His father, Irving Charles, was an electrician. Toni believed her son would be a star—a psychic told her so before he was born. “The psychic said, ‘It’s a boy, and he’s going to be famous,’ ” RuPaul says. “So I grew up knowing that.”

Toni and Irving had moved to California from the South—“Ru” was a play on roux—during the Great Migration. Their marriage was tumultuous. They separated when Ru was five, divorced when he was seven. Toni fell into a depression, and his twin sisters Renetta and Renae, seven years older, became the adults of the household, looking after “Ru-Ru” and his younger sister, Rozy.

Despite her depression, Toni, “a very fiery, world-weary person,” says Ru, retained a sense of humor. When he asked why she gave all four children the same initials (R.A.C.), she told him that it was because they were “real-ass crazies.” Toni was also accepting of her son. “There was no shade to me playing in makeup, wearing my sisters’ clothes, doing whatever I wanted to do,” he says. “I never had to ‘come out,’ because I was never ‘in.’ It was understood that Ru was Ru.”

The twins taught Ru-Ru about Diana Ross and Cher. When Renetta attended the Barbizon School of Modeling, she showed him how to walk a runway. Monty Python’s Flying Circus was pivotal. He was drawn to the irreverence—and to the nudge-nudge, wink-wink way the show seemed to break the fourth wall. Ru thought,“There’s my tribe.”

By the time he was thirteen, RuPaul was carrying a Magic Marker at all times so that he could write “Bowie” on everything that wasn’t moving. “We can’t articulate our feelings at that age,” he says, tears in his eyes. “But we can point and go: That’s me right there.” Ziggy Stardust represented, to him, nothing less than freedom. “A person who isn’t shackled by societal conformity, who can color your hair, wear makeup,” Ru says. “My God, so much freedom.”

In the summer of 1976, RuPaul moved to Atlanta with Renetta and her new husband, Laurence. Ru enrolled in the Northside School for the Performing Arts and saw The Rocky Horror Picture Show, went to his first disco—and saw his first drag performance: Crystal LaBeija singing Donna Summer’s “Bad Girls.” (Don’t judge, but he thought it was Donna Summer.)

His own music career officially began with RuPaul and the U-Hauls, an art band he formed in the early eighties. Soon he was making guest appearances with the B-52’s-esque Now Explosion, and fronting a New Wave/punk band called Wee Wee Pole, combining a loincloth, a Mohawk, thigh-high wader boots, and football shoulder pads for a look he named “gender fuck.”

He created more personae: Starr­booty, inspired by the over-the-top Blaxploitation films of the 1970s, and another he calls “street-hooker Soul Train dancer.” By this point—the late eighties—RuPaul was living off and on in New York, go-go dancing at the Pyramid and other downtown clubs. In August of 1989, he was crowned, on the underground scene, the Queen of Manhattan.

Two years later, while living in the Meatpacking District, surviving on free popcorn and seltzer water from the Film Forum, he recorded his first demo. In 1992, on the day of his thirty-second birthday, he released “Supermodel,” which he’d written with his friend Larry Tee. The single rose to No. 2 on the Billboard dance-song chart, and designers like Isaac Mizrahi and Todd Oldham featured it in their runway shows. “How smart of him to take this word that has just been adopted into the O.E.D.,” Mizrahi recalls, “and do this insane song about it, and turn it on its ass, and then turn it back on its head.” Kurt Cobain declared it one of his favorite songs of the year.

By 1994, RuPaul had become the first drag queen to land a major makeup deal, as the face of MAC Cosmetics in a campaign that declared: “I am the MAC girl.” (“What better way to show the power of makeup than if a six-foot-four black man can look like a supermodel?” he says.) Then came The RuPaul Show on VH1, which ran for 100 episodes and placed him on the cusp of the mainstream. As he explains it now: “I said: I’m RuPaul, Supermodel of the World. And the world said: Yes. You. Are.

THE SECOND REIGN of RuPaul has already lasted twice as long as the first one—and shows no signs of weakening. It began, of course, with the 2009 premiere on the Logo network of RuPaul’s Drag Race, yet another perfectly executed piece of satire, this time of our reality-TV era. The series, now in its eleventh season and on VH1, took what had been a subculture and exploded it, minting drag-queen stars, mainstreaming idioms, remaking Ru into a kind of self-help guru—and winning nine Emmys along the way.

Because this is 2019, RuPaul also has a successful podcast, “What’s the Tee?,” through which he broadcasts Ru-isms, teaching the good people of RuWorld how to “listen to the universe’s stage directions.” Come May, he will preside over the fifth RuPaul’s DragCon in Los Angeles, the massive drag-culture convention he created with his friends and collaborators, the producers Randy Barbato and Fenton Bailey, in the mold of Comic-Con. (The festival is now bicoastal, with a second convention held in New York every September.) And he will debut a makeup collection he designed with Roncal, whose Face Defender he swears by.

Ru divides his time between L.A. and Wyoming, where his husband, Georges LeBar, owns a 60,000-acre ranch. LeBar is from Perth, Australia—he inherited the ranch from an American grandmother—and he is even taller than RuPaul. (Six-foot-seven!) When Ru is at the ranch, he tells me, “I usually wear fabulous Westernwear: denim concoctions, turquoise jewelry, gorgeous hats, Italian cowboy boots.” The couple do not have kids, nor plans to have any. “I like peace and quiet a lot,” Ru says. When Ru has time off, they like to travel—often to Las Vegas to see the latest big residency on the Strip (Cher, Jennifer Lopez), to New York, or to Paris. (Ru jokes that his Aussie mother-in-law pronounces the Champs-Élysées “Chomps Elsie.”)

Georges, who has never given an interview and declined one here, met Ru on the dance floor at the Limelight in 1994, and they have been together (mostly) ever since, aided by the fact that they keep the relationship open. “I love him too much to try to put shackles on him,” RuPaul says, again with tears in his eyes. “Love is free. It’s not that sort of romantic surface thing we all bought into. He is my most favorite person that I’ve met.” Besides, he adds, “Gore Vidal said you should never pass up an opportunity to have sex or be on television.”

Which brings us back to AJ and the Queen. It’s based on the 1941 Preston Sturges comedy Sullivan’s Travels, a favorite of both RuPaul’s and King’s—which they discovered when they met for the first time, in King’s office, where a movie still hangs on his wall. (That, right there, is what you call a cosmic stage direction.) When fashion designer Zaldy, responsible for RuPaul’s looks for Drag Race, saw the script, “my jaw dropped,” he tells me. There are love scenes, for one thing, but also the kind of drag numbers that will require “performancewear”—for, say, flying through the air on a harness.

There’s another element of surprise, King tells me, one that longtime RuPaul fans might find shocking. The series shows Ru’s character getting into and out of drag. “You’ve seen Ru, and you’ve seen Mama Ru,” says King. Here “you see him midway.”

The day before I met Ru for coffee, King had shown him the first completed episode of AJ and the Queen. Ru had been nervous about what it would reveal. “In my career, I’ve been able to show certain angles. I’ve been able to paint on a face and edit what I presented,” he explains. “I thought by doing this acting project, I would be exposing myself to the world: the raw, unfiltered self.”
He goes on: “But what I found out yesterday was that I was exposing myself to myself. I got to see the parts of me that even I didn’t allow myself to recognize or acknowledge. I had thought, I’m going to be naked to the world. No, I was naked to myself.”

In this story:
Produced by Lauren Beyda for Portfolio One.
Costume Designer: Shana Albery.
Costume Construction: Shana Albery.
Creative Producer: Kathryn MacLeod.

Watch RuPaul’s 7 Rules for Rocking the Red Carpet: