The Complete Oral History of O, The Oprah Magazine (2024)

We've heard it many times over the past 20 years: “What’s it like to be at O?” Curious reader, wonder no further! Here’s a behind-the-scenes look at the people, parties, food, fun, meetings, madness, misadventures, and thrills— told by the people who were there as it happened.

IN THE BEGINNING

GAYLE KING, O editor at large: Oprah had been asked by a lot of publishers to do a magazine. She took the meeting with Hearst because of Ellen Levine, who we call Queen Levine. We were familiar with Ellen because she was editor in chief of Good Housekeeping and had been on TV quite a bit.

CATHIE BLACK, former president of Hearst Magazines: Ellen and I set up a meeting through Oprah’s business manager. There was never a promise that Oprah herself would show up, but when the day came, she burst into the conference room like a 2,000-watt lightbulb.

GAYLE KING: She was blown away by their presentation.

CATHIE BLACK: Ellen had the idea that we should make a video, so we sent a crew out to a shopping mall inNew Jersey to ask women whether they watched her show and how they’d feel about a magazine. They went crazy. Oprah was riveted. She said, “Do you really think they’d like it?” We said,“Yes, Oprah, they really would.” Then Ellen said, “You’re a woman of letters. You love the written word. You love to connect with readers on your show.”

GAYLE KING: That's what got her.

CATHIE BLACK: Since Oprah was in Chicago doing the show, we wanted someone at the magazine who really got Oprah’s vision, and we thought Gayle would be great.

GAYLE KING: Oprah told them I’d never do it. But I was in the middle of contract negotiations at the TV station in Connecticut where I’d been for about 18 years, so I asked her, “Well, what would it be exactly?” She said, “I don’t even know.”I told Hearst: “Look, I have no magazine experience. I’m a TV baby.” They said,“But you know Oprah, and you know a good story.” I think it was three years before I stopped calling readers “viewers.”

ELLEN KUNES, O’s first editor in chief: Oprah and Gayle said, “Tell us how you sum up your vision for this magazine.” I said, “I see it as the personal-growth guide for the new century.” Oprah jumped up and said, “That’s it!”

GAYLE KING: Every other magazine had done “Thinner Thighs in 30 Days.”Oprah said, “I want women to feel good about themselves, and I want to meet them where they are.”

OPRAH WINFREY, O founder and editorial director: I envisioned a manual that would allow readers to see themselves in the pages and would reflect their lives back to them in the most aspirational way.

CATHIE BLACK: We thought about calling it A-Ha or Spirit.

OPRAH WINFREY: Or Glow, with OW at the end. I don’t know who finally said O, but it was the right call.

THE EARLY YEARS

AMY GROSS, O editor in chief, 2000–08: People would ask how it was to work with Oprah. I’d say, “I steer the ship, but she’s our North Star.”

LISA KOGAN, O writer at large: Amy Gross made a list of words we were forbidden to use. She wanted O to sound the way real people talk—no “tresses,” “elegant,” or “thoroughly modern” anything. She didn’t want to use clichés that made women seem less serious or interesting than they really were.

DEBORAH WAY, O deputy editor: Amy was a major Buddhist, which really informed our content. So. Much. Mindfulness. So much letting go.

AMY GROSS: I had a little bell on apiece of plain wood, very Japanese, and I’d walk down the hall to our planning meetings, ringing it. To me, it set a great mood—anticipatory, collaborative, getting excited about ideas together.

DEBORAH WAY: It’s a chime, but we call it “the gong,” and it’s still a big part of life at O. The editor in chief’s assistant is the one who strikes it with the little mallet. When someone new takes over that role, there’s a lot of pressure to get it right—not too loud, not too soft. You can’t just bang a gong!

COVERS

ADAM GLASSMAN, O creative director: In the beginning, the covers were like a more typical women’s magazine, just Oprah looking warm and approachable. Then we thought, We should go on location and have Oprah doing things.

OPRAH WINFREY: The hardest shoot was the one where I was riding a horse and trying to get him to hit a specific mark for the camera. The horse kept going too far, and they’d say, “Go back and try again.” Holy God. And then after we finished it, people assumed it had been Photoshopped! People, I was on that horse!

ADAM GLASSMAN: After 9/11, we did an issue about celebrating New York, with Oprah on a double-decker bus on Fifth Avenue. Services were letting out at St. Patrick’s Cathedral, and people looked up and lost their minds. They’d just spoken to God inside, and then they walked out and saw Oprah.

STEPHEN BROWN, set stylist and creator of Glitterville Studios: We did a December cover with a big teddy bear, and Ruven Afanador, the photographer, wanted her to sit on it. But it wasn’t stable, so I had to sit underneath it with one leg propped behind me like a tripod, and then Oprah came and sat on the bear, which was on top of me. I thought, Oh Lord, what if I dump Oprah on the floor?

LUCY KAYLIN, O editor in chief: In 2013, we thought, Wouldn’t it be amazing if Oprah could do a major hair moment? Hair is such a big deal—it’s personal, sexual, social, racial, political. Adam Glassman and hairstylist Kim Kimble, who worked with Beyoncé, came up with this incredible wig they called Wild Thang.Oprah had to be helped onto the set because she was balancing three-and-a-half pounds of hair on her head.

JOSEPH ZAMBRANO, O social media editor: Sometimes we shoot four covers in a day, so the playlist is key to keeping up Oprah’s energy. A couple of years ago, we were at a shoot where she was just not feeling it, and I cued up “Despacito.” Her mood shot up—she was dancing and shaking. I think of the playlists as soundtracks. If she’s channeling DianaRoss, that’s what we play. For September 2018, when she wore the yellow hat and glasses and scarf, she reminded me of a Latina woman on vacation, like my mom, so I played “Havana” by Camila Cabello.

Made With Love

Readers have sent gifts featuring Oprah and Gayle rendered in macaroni, wood, icing....

MEMORABLE STORIES

GAYLE KING: In 2002, Oprah had the first interview with the Central Park jogger. It was a different experience for her, interviewing for print versus TV. There’s an intimacy when you’re just sitting there with your recorder.

AMY GROSS: And we did crazy things, like a disaster preparedness guide about how to handle scary—if rare—situations, like falling into quicksand.

CHRISTINA WEBER, O executive visual director: For a fashion story, we went out on the street in New York with different animals. There was a little pig named Peaches, and we put her in baby-size pinkConverse high-tops. A cop pulled me aside, and I thought, Uh-oh, is there some permit I don’t have? But he said, “Could I get a picture with the pig?”

LISA KOGAN: When I interviewed Oprah and Gayle together, I thought, What don’t they know about each other? But Oprah had a few things. She talked about standing at Gayle’s wedding as her maid of honor while Gayle was saying her vows, not convinced the marriage was going to work. Gayle was shocked; she’d never heard that before.

SUSAN CASEY, O editor in chief,2009–13: For the November 2012 issue, Oprah interviewed the Obamas and the Romneys. Her conversation with the Obamas was spellbinding. I still have the recording on my phone. Then we went to the Romneys’ summer home in NewHampshire. We stopped at a little motel so Oprah could get dressed and have her hair and makeup done. Some locals drove up to find Oprah Winfrey standing outside in her curlers.

Guests of Honor

Just a few of our favorite visitors to the O offices.

LUCY KAYLIN: I think our package about caring for your aging parents is one of the best things we’ve done. It could have been unbelievably depressing, but the editors came up with lyrical, smart, funny, serious, silly, amazing, enlightening stories. We won an ASME for it—the magazine equivalent of an Oscar.

LEIGH HABER, O books editor: Michelle Obama’s Becoming embodied everything you want in an Oprah’s Book Club pick—reflection, introspection, inspiration. Oprah filmed a conversation with Mrs.Obama in the Hearst building, and that became the big launch event for the book.

AMY MACLIN, O executive editor: I think a lot of people were still feeling that the world had been turned upside down since the 2016 election, and Oprah asked Mrs. Obama, “Are you optimistic about our country?” She nodded at these young girls in the front row and said, “We have to be.” Her voice broke a little. I cried.

HOLLY CARTER, O style features director: I was wearing the dress I wore to my mother’s memorial because I wanted her to be there in some way. After the interview, as Mrs. Obama was walking by, she told me, “I have that dress. I wore it in Qatar with Barack.” It was like my mom was there, making sure I got my moment.

FAVORITE THINGS

ADAM GLASSMAN: Favorite Things has always been one of the most popular features in the magazine. Oprah’s love of gift giving is so infectious. And there’s that Saturday Night Live parody with people’s heads popping off.

RAE ANN HERMAN, O contributing style editor: We look for Favorite Things all year round, but it really starts ramping up inMarch. We wind up with a list of 800 to1,000 items, which we whittle down until we’re at about 300. Then we have a big run-through with Oprah.

OPRAH WINFREY: I don’t eat anything else that day, and I drink a lot of water. When you try a shot of tequila or drink some Champagne and have a biscuit and a piece of cake—six hours later, your sugar levels are not good. I pace myself, like I’m doing a marathon. Actually, doing a marathon is easier.

ARIANNA DAVIS, O digital director: Every year we have a sweepstakes where we give away all the Favorite Things to 12 winners. When I was an assistant here, part of my job was calling the people who won, and some of them screamed so loudly I had to hold the phone away from my ear. Or they’d think it was a prank call and hang up.

ZOE DONALDSON, O associate editor: The staff actually wraps the gifts for the winners—every single gift, we’re talking hundreds—which is a Christmas miracle.

DEBORAH WAY: Some of us are really good wrappers, some are pretty remedial. And then there’s Amy Maclin, who’s not allowed to wrap anymore.

AMY MACLIN: Even when we have840 boxes, it’s like, “Thanks, but no thanks.” That’s how bad I am.

GLORIOUS GAYLE

ADAM GLASSMAN: Gayle is the least jaded person I know.

AMY MACLIN: People get so excited when they see Gayle in the cafeteria. It’s like “Stars—they’re just like us!”

GAYLE KING: I’m always amazed that people want to watch me bebopping down to pick up my cauliflower wrap. Oh my God, that cauliflower wrap!

ZOE DONALDSON: Gayle’s office—with its giant TV—is where we gather when something big happens, whether it’s Aretha Franklin’s funeral or the Brett Kavanaugh hearings. She always wants to know our opinions.

DEBORAH WAY: Gayle is truly interested in people and their stories. She’d have a conversation with every human being on earth if she could.

J.J. MILLER, Gayle’s former assistant: I wish I could lead as gracefully as Gayle. Sometimes when I proposed ideas, I’d get her trademark email that led with “Hmm...not so sure about this.”Eventually, I realized that was her nice way of saying, “This idea is bullsh*t. But I appreciate what you’re trying to do.”

LUCY KAYLIN: Gayle knows instantly whether something works for this magazine, and it’s never as simple as “Oprah doesn’t like that color.” It’s always something more nuanced about what’s right and good for us and for Oprah.

DEBORAH WAY: Once, after a challenging situation when Gayle’s wisdom pulled us through, we said, “We should have a Gayle King Appreciation Day.” I thought it would be fun if we all came to work wearing clogs, Gayle’s signature office footwear, and yellow, her favorite color. But it turned out her 60th birthday was coming up, so Gayle King Appreciation Day turned into a surprise party.

ARIANNA DAVIS: We had her favorite grilled cheeses and cupcakes, we all wore yellow, and we ordered clogs for everyone.

JOSEPH ZAMBRANO: Oprah had a cover shoot that day, so we set up the party in another photo studio down the hall. Then we told Gayle that Jennifer Aniston was there and wanted to say hi. When Gayle walked in, she was so surprised, she jumped. She saw Kirby, her daughter, and thought, Why is Kirby here with Jennifer Aniston?

DEBORAH WAY: Her son, Will, who was living in California at the time, jumped out from under a table. She was really surprised by that.

WHAT WE DID FOR LOVE

AMY MACLIN: We’ve had a lot of adventures at this magazine—all in the name of journalism, of course.

ZOE DONALDSON: I tried vagin*l steaming. And watched feminist p*rn about a couple putting together IKEA furniture. And had a bird-poop facial.

HOLLY CARTER: I modeled bubble-booty jeans for a denim story, but I didn’t make the final version. My butt got cut.

LISA KOGAN: I joined Oprah in her stretching workout, which required me to put on a leotard and have my limbs pulled, Spanish Inquisition–style. I have shopped for sex toys. I have spent the entire day in a closet with Adam and Gayle. Twice.

MOLLY SIMMS, O senior editor: I learned blacksmithing at a North Carolina folk-arts school. I did ecstatic dancing, two hours of people undulating on the floor. I went to a marijuana tea party.

AMY MACLIN: I went to a spa where you subsist on a liquid clay concoction and have daily colonics. It was like getting baptized from the inside. I went to theSchool of Life in London to learn how to fight existential despair and face death.

NAOMI BARR, O research director: Once, not long after my mother had died, I was checking facts with a woman we were featuring in the magazine. We ended up talking about loss, and I teared up and told her my makeup was running. Later she mailed me a tube of mascara, and on the package she’d circled the word waterproof and added an exclamation point and a smiley face. I still have it.

What A Find!

We get a lot of loot in the O offices, and whenever anyone receives something they can’t use, it goes to the Free Table in hopes of finding a happy home....

AHOY!

ASHLEY O’BRIEN REILLY, O executive director, marketing and promotion: We started our O cruises with Holland America Line in 2017, Oprah’s Year ofAdventure. The first went to Alaska, where Oprah had never been.

JOSEPH ZAMBRANO: Oprah got so excited about the bald eagles—she was filming everything on her phone. The captain saw her focusing on this one bird and had to tell her, “That’s a pigeon.”

STEPHEN BROWN: The photo crew took a helicopter out to a glacier to prep for our cover shoot, and a thick fog descended, so for the next two days, we were stuck in the dog mushers’ camp. We had two movies to watch: The Revenant—not ideal when you’re stranded on the frozen tundra—and Sausage Party. Adam Glassman joked, “This might be the last movie we ever see.”

LUCY KAYLIN: The cruises are off the hook—more than 2,000 of the Oprah faithful on this floating disco/meditation room/food orgy.

JAYNE JAMISON, O senior vice president/publisher: Seeing all those like-minded women at the pajama party on the Girls’ Getaway Cruise where Oprah was handing out tequila shots—that will forever be one of my career highlights.

HOLLY CARTER: There’s so much joy, but also a lot of people have been through life-altering things, and they’ve come to see Oprah and heal. There’s something really moving about that.

DEBORAH WAY: This magazine means a lot to our readers, and they mean a lot to us. We call them “our ladies.”

OPRAH WINFREY: The readers are an extension of myself. Everybody who gets this magazine is a woman who is constantly reaching for the higher ground of her own life. I’ve always had that woman in my heart because she is my heart.

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