Blowing Our Cover: Behind the Scenes With Oprah

It is 7:55 a.m. on December 8, 2000, and I would sell my soul for anything caffeinated. Instead I open my notebook, take out a pen, and knock at the door of the presidential suite of the hotel where Oprah Winfrey and about a dozen crew members have spent the night. We've come together in South Carolina to shoot our March cover, hoping to find what most of the country will be craving when this issue of O hits newsstands across America: a little taste of spring.

The concept is pure Oprah. "So many women, myself included, see a magazine and think, Now, why don't I look like that?" she says one day during an ideas meeting. "Let's show everybody what being a cover girl really takes." I'm a little stunned by this suggestion. Even 20-year-old models who purport to be wearing no makeup in front of the camera cheat, refining their complexions with artfully applied foundation, concealer, and blush. A couple of thoughts occur to me: 1. Oprah's been working awfully hard—is it possible that she's maybe, oh, I don't know, lost her mind? 2. Who's the poor slob who's gonna have to describe how her boss looks minus all form of cosmetic enhancement?

The team landed in Charleston last night, armed with scrim and bounce cards, lenses and light meters, wind machines and filters, mirrors and makeup brushes, curling iron and styling gel, trunks of wardrobe, an assortment of props, CDs, oatmeal cookies, potato chips, and bottled water. Photographer Art Streiber, along with his shaggy band of technicians, has come to shoot Oprah. Lisa Elwell and Celeste Brown, O's fashion director and assistant fashion editor, have come to dress Oprah. Gayle King, Carla Frank, and Karen Frank—O's editor at large, design director, and photo director—have come to lend their expertise and support. Andrè Walker, Reggie Wells, and Audrey Allen are here to be Oprah's hairstylist, makeup artist, and stand-in. Oprah is here to be Oprah. They've all come to make magic. And I've come to reveal their tricks.

"My face is still in Chicago," Oprah announces as she ushers me (a.k.a. the poor slob) into the suite. Her hair is flat, her eyes are puffy...it happens to the best of icons. Andrè Walker is heating his curling iron while Reggie Wells sets up a makeshift makeup station near the window. Oprah takes a final bite of boiled egg, grabs her cup of tea, and joins them. It is a well-choreographed routine, casual yet precise. They've been a threesome for years, finishing one another's stories, serene when stillness is required, funny when it's not. While Andrè decides that an impromptu trim is in order, draping a shmatte over Oprah's pink pajamas and picking up his scissors, I ask Oprah if she ever goes out in public in this...uh...condition. The three of them break up. "All the time," she says laughing. "Years ago in Nashville, this woman starts following me all around the Kroger. Finally she says, 'Oprah, is it you? Well, I thought so, but I couldn't imagine you'd come out looking like this.' Another time, a woman walks over—Oprah leans in conspiratorially and whispers—"'Oh, I get it, you're incognito!' I said, 'No, ma'am—that's just my face.'"

Andrè blows Oprah's hair as I persist. "So you don't feel better in makeup?" "No," she answers, "makeup doesn't make me feel better. It makes me feel made up." She takes a last sip of tea and moves to the makeup chair. "I think the older you get the more secure you get, and you stop caring so much about how you look." Reggie does an eyebrow cleanup as she goes on. "When I was doing local news, they were always trying to redo me." Reggie tilts Oprah's chin up and begins erasing all signs that she spent the night grading papers. "They asked me if I was willing to have surgery: My eyes were too far apart. My nose was too wide. My hair was too thick. Talk about a challenge to your self-esteem!" It's time for the eyelashes. "I've used eyelashes every day since I've been on TV."

It's true, the lashes make an enormous difference. But any thoughts I have of going into Walgreens a writer and coming out a cover model are interrupted by Reggie. "Hey, Mary"—his term of endearment for Oprah, or anybody else he particularly likes—"what's that on your chin?" he asks, pointing to a slight blemish.

"What can I tell you?" Oprah says. "It used to be the size of Maine, now it's Rhode Island." Reggie gets out his Oxy 10 and starts dabbing. "What we really need is Oxy 22, but it hasn't been invented yet," he says. On that note, Oprah returns to Andrè, who irons fat curls into her hair.

"Don't you comb that out?" I ask

"No, I'll wait till we're ready to shoot," says Andrè.

"My hair has a long day ahead and it refuses to do anything after four o'clock," says Oprah.

"So you're just gonna walk through the hotel lobby like that?" I ask, sounding more like my mother than I would've believed possible.

"I have no vanity," Oprah says. "I kept thinking it would come at 30, then at 40...."

Next: Oprah goes through 19 (yes, 19) wardrobe changes