Photo: Art Streiber
Hair, makeup, music. Lights, camera, action, and a cast of thousands (well, at least a couple of dozen). Lisa Kogan reveals just what it takes to create a cover girl.
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
Oprah stops as Reggie applies lipstick and Andrè checks her new trim from every angle. "I think Mary's eyes are her special quality, but she likes lip," Reggie says.

"I blend two or three lipsticks together," Oprah says. "That's the way makeup artists do it. You know those cover credits that say the model is wearing such-and-such lipstick? It's usually not true. The reason lipstick looks different when you get it home is that it's one color instead of a combination." Andrè and Reggie nod in agreement. "Once you start allowing yourself to fudge the truth in any way," she adds, stepping out of the chair, grabbing her street clothes, and heading for the bedroom to get changed, "you no longer have your own barometer."

When we arrive at Lowndes Grove Plantation, Oprah goes straight to the veranda where the photo is set to be shot. "So I can see what I want to feel like," she says, checking out a rocking chair and a vase full of blue irises.

Somebody puts on Paul Simon's "Graceland" as we enter a bedroom filled with two long racks of clothing, 28 pairs of shoes, 23 shawls, 14 bracelets, a dozen pairs of earrings, and too many necklaces to count. Oprah, Gayle, Lisa, Carla, and Celeste focus on a coral top and tangerine bottom. I point out the two don't really match, but Carla assures me that she can fix it in postproduction.

Oprah goes through 19 wardrobe changes as opinions ricochet around the room: "Too dressy, too tight, too baggy, try it with that necklace, this sweater, those pants. That's lifting her face. That's hitting her hip. Take her watch. Hold her earrings. What about a crisp white blouse? Slip these on. Try a different bra."

Karen knocks at the door. "We're losing our light," she says. "Let's go." Reggie fine-tunes Oprah's makeup. Andrè combs out her hair and gives it a good spray. For the rest of the day, he rarely looks away from her. If something's off, he'll catch it before almost anyone. "There's a girl in New York City / She calls herself the human trampoline," Simon sings as Oprah closes her eyes, takes a deep breath, and prepares to be shot.

We all fade into the background. This is a private affair, strictly between Streiber, Oprah, and the camera. Click, click, click. "Pull your stomach in. Sit up straight. Dip your right shoulder. Rest your hand. Hips toward me." Click. "Scotch-tape her necklace up in back, it's falling too low. That's better." Click. "Tilt your head. Beautiful." Click, click. "Lose the necklace. Change the music. Get a book on her lap. Throw some color on her shoulder."

"Is this an accent or an accident?" Oprah wonders aloud as she studies the chartreuse pashmina that's been draped across her shoulder. A new wrap instantly appears. She picks up one of the many Polaroids that a photo assistant is snapping. "I'm looking at the overall structure of the photograph," she tells me while Streiber & Company adjust the lights. "I'm trying to see how I fit into the space." Oprah pauses, taking in the scene. "Every shoot has its own rhythm—and we haven't found ours yet."

"One more roll, Oprah," Streiber cajoles. "And this time, let's go a little self-esteemier." Oprah laughs. Click. Aretha sings about a rose in Spanish Harlem. Click. "Big smile, Oprah."

"What are my breasts doin'? Where are the girls? Are they up?" Oprah shouts over the music.

"You could put an eye out with one of those things!" Streiber shouts back.

"Her sweater's bunched up," Gayle calls.

"See," Oprah says as Celeste adjusts her top, "I've got a bunch-up watcher. That's what makes you look good." Oprah strikes a few more poses in a few more outfits, and we all head downstairs to the dining room for lunch. "Okay, people," Streiber announces. "Let's go fly a kite."

After a quick hair-and-makeup fix at our Fort Sumter National Monument location, Oprah changes into a thin purple sweater and slacks and heads to the field, where, with the help of a few good men and an industrial-strength wind machine, she will fly a kite for the first time in her life. The temperature has dropped along with everyone's blood sugar. "I hate this acting hot when it's cold," Oprah says to no one in particular. She is given a fast lesson in the theory of flight, but it is assumed a crew member will actually keep the thing airborne. "I was a deprived Negro child," Oprah drawls, perfectly deadpan. "We couldn't afford the wind. Never caught a breeze till I was 22."

"Let's do this," Streiber yells—part adorable kid brother, part General Patton. "Big smile, Oprah."

"This is a big damned smile" comes Oprah's reply. The kite takes a nosedive in a matter of seconds.

"Try again," Streiber says, determined to make it work. But this time some of us have found our way into his shot. "Everyone step back, please. And somebody crank up the music!" he shouts.

"My hair's good for one more hour," Oprah warns. "My face is halfway back to Chicago." She tries not to shiver. As if on cue, the wind picks up and the music kicks in. "You better be good to me / That's how it's gotta be," Tina Turner sings, loud and proud. Oprah starts to move. We all start to move—including Oprah's kite. It swoops, it glides, it soars, it dances neon red against a sky streaked with gray. "Hey, Lisa," Oprah calls to me as the kite floats higher, "we just found our rhythm."

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