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On a bright, temperate afternoon, Oprah Winfrey — still in full hair and make up from a daylong shoot for O, The Oprah Magazine, sat comfortably on one of the two smooth, black leather sofas in her makeshift dressing room at Chelsea Piers on the west side of Manhattan.

Dressed casually in a vibrant orange sweatshirt with white piping and a pair of cuffed, dark jeans, Winfrey, 61, joked about her years in the limelight, noting that she’s appeared on the cover of O for 15 years now, and was ready to retreat from the spotlight. The media mogul began her career more than 40 years ago, starting out as an anchor in Nashville. She then moved to Baltimore in 1976, where she coanchored the evening news, and would meet her best friend Gayle King, who worked on the newscast as a production assistant and writer. Two years later, Winfrey entered the burgeoning talk-show market as a cohost with Richard Sher on “People Are Talking.” In 1983, Winfrey would move to Chicago and host a 30-minute morning talk show called “AM Chicago.” Her ratings skyrocketed and she signed a syndication deal with King World. The show was renamed the “Oprah Winfrey Show,” and it was expanded to a full hour and broadcasted nationally in 1986. The show became the number-one daytime talk show in America, and Winfrey began evolving the programming to include weightier topics, such as geopolitics, gay rights, race issues, substance abuse and cancer. She balanced those subjects with celebrity interviews and audience gift giveaways.

This story first appeared in the April 29, 2015 issue of WWD. Subscribe Today.

Her best-known giveaway show ignited a kind of pandemonium when she gave every audience member a car. Asked how she came up with the now-famous phrase: “You get a car, and you get a car,” Winfrey told WWD: “I wanted to shock them by repeating, ‘you get a car.’”

It worked. Winfrey’s show remained on the air until 2011. During her time as host, Winfrey had other television, film and theatrical projects brewing. Her focus shifted toward the development of TV channel OWN, which is a joint venture between her company Harpo Productions and Discovery Communications. OWN experienced some bumps in the beginning with lackluster ratings and an executive-management shake-up. But the channel has since rebounded and is now cash-flow positive, due in part to a slate of Tyler Perry shows bringing in strong ratings. Winfrey, who is estimated to be worth about $3 billion, is also focusing more on film production with recent projects including “Lee Daniels’ The Butler” and “Selma.” Last fall, she hit the road for her “The Life You Want” cross-country tour, a quasi-evangelical, self-help, feel-good conference of sorts.

Back in New York, an affable Winfrey — with e-mail-checking bestie King in tow — kicked up her feet on a nearby coffee table and chatted about her media empire, her cultural legacy and whether she misses appearing regularly on television.

WWD: How has O changed since it launched 15 years ago in light of the changing media landscape?
Oprah Winfrey: I think the change has really been with — well, we’re affected by ad sales like everybody else — I remember when we started the magazine, we were charging, literally — we gave more value per page because everybody underestimated. I was told when we started this magazine that it would be five years before we’d be in the black. Five years, so don’t be discouraged. Hang in there. It’s going to be all right, but it’s going to take you five years. The first month, we oversold by, I think 500,000 copies or something. We were off to the races. That was pretty exciting.

We’ve seen the ad sales landscape, the financial landscape, change for everybody actually, in the business.

WWD: In order for magazines to grow, many brands are trying to expand their readership by targeting Millennials. Are you looking to bring those readers in as well?
O.W.: I think we try to speak to the heart of the woman who we know is interested in growing into herself. Obviously, I think that the idea of reaching young girls that are in college is something that we are strongly open to because who better wants to know how to live a more purposeful life than people who are starting out? But what we really try to concentrate on is the heart of our reader. We know who she is. We know where she lives. We know that she’s into her mid- to late-40s. We know that she cares about a lot of different things, and is juggling a lot of different things, and so what we try to do is to speak to, and hit that nerve, on a regular basis. I think we do speak to all ages, but the emphasis is, unlike everybody else who is chasing the Millennials, we are not chasing the Millennials.

RELATED STORY: Oprah Winfrey Celebrates O Magazine’s 15th Anniversary >>

WWD: Where do you see the magazine going in the future?
O.W.: I do not see myself on the cover for the next 15 years.

WWD: When will that end and how?
O.W.: Well, we actually seriously considered it for now, and made the decision not to do it now. I can guarantee…

WWD: You don’t want to be pushing a walker on the cover?
O.W.: Rolling myself out? [Laughing] I’m amazed that we don’t run out of ideas. I’m amazed at the number of poses that I’ve been able to do. I’m amazed that there’s still a way to clap my hands, smile or raise a thumb. I don’t have another clap in me, or another smile or another way to turn my head to the left. There’s not enough wind machines.

WWD: How do you see your own impact on media over the years? How do you view what you’ve accomplished?
O.W.: That is such a crazy question, Alex. Let me tell you why that’s a crazy question. It’s a crazy question because I don’t know what kind of egomaniac is sitting at home thinking about the impact they have had on the culture. It’s not something I actually think about until it comes up. I was in a conversation a couple of days ago and someone said: “You know, we were talking about the whole issue of transgender and how it has become so accepted now, and somebody said, ‘You know the Oprah show, I think has had a big impact.’” I said, I don’t think so. We did several transgender [shows], but we didn’t do as much for transgender as I did for, say, abused kids or battered women. And they said, “But no, you started the conversation. You started the conversation and the conversation has led us to here.”

So yeah, I remember when we were doing coming-out days for gay kids who couldn’t tell their families, but they could come on the Oprah show and tell me. So, the impact, to give the long answer to your question, the impact of the magazine, the impact of the show, the impact that I have had on media is what Maya Angelou says will be my legacy. I remember saying to her one day, “I think my legacy is going to be building the girl’s school in South Africa.” And she said: [imitating the booming, baritone quality of Angelou’s voice] “My dear, your legacy is every life that you’ve touched. It’s everybody who has been moved by anything that you say, anything that is written, anything that has come out of these pages. That’s the legacy.” That’s a long way around it. I don’t think about it.

WWD: If you were starting your career today, how would you navigate it? Would you have a YouTube channel or a blog?
O.W.: I’d be so confused. You know why? [In Angelou voice] “Back in the day when I started — it’s like I walked five miles to school in the snow barefooted” — there were three channels. I don’t know what I would do. I’m really glad to be evolving at this time and not having to be in a position to figure it out, but we are constantly — not figuring out how to begin because we’ve got a really solid foundation — but we’re constantly, as a magazine, trying to grow ourselves to the next level, expanding our digital platform, and connecting with readers there, and trying to explore our abilities to bring our magazine to life. It’s a growth process, but I’m glad we’re not just starting out. God bless you, Alex.

WWD: Please talk about your affection for print and the volatile environment that is pressuring its existence. Is it still as valued in today’s landscape?
O.W.: That’s a blasphemous question!

WWD: How does the content of your magazine stand out from all the women’s magazines?
O.W.: It’s mind food.

Can you talk about how OWN relates to the magazine and what sorts of projects you would like to work on in the future for the network?
O.W.: I think that this past fall, all of the platforms sort of came together with the tour that I did. The magazine was involved, OWN was involved, obviously, I was, and the truth is, all of them center around the central idea of connecting to the viewer, connecting to the reader in such a way that people feel valued, and people feel that their voices, whether on the pages or on the channel, are being represented.

WWD: Documentaries are so in right now. Would you consider getting involved in that area in a more meaningful way?
O.W.: Documentaries? No, not as much, because I tried documentaries [in the early Aughts]. It wasn’t the time for me. I was going to try to do the same thing, I did make a valiant attempt but it did not work — to do the same thing with documentaries that we had done with the book club [in 2011]. The zeitgeist wasn’t ready. It just wasn’t ready. We tried and tried — 18 to 49 [makes a negative buzzer noise]. But now, that is something I would absolutely reconsider. But what we’re really trying to focus more on the network now is scripted television.

WWD: What subjects attract you the most?
O.W.: I’m always interested in people being able to share stories that allow us to see the landscape of human foibles, challenges, and ultimately triumph.

WWD: Do you miss interviewing people?
O.W.: No.

WWD: You don’t miss this?
O.W.: There’s not another darn thing I can say. I interviewed — no — had lunch with Harper Lee several years ago, trying to convince Harper Lee to do “To Kill a Mockingbird” for the book club. She wouldn’t do it. She said, “Honey, I said everything I wanted to say.”

WWD: But now look at her.

O.W.: Now look at her! But, interviewing people, I don’t miss that at all. I do miss kibitzing with the audience because after every show I would spend half an hour to 40 minutes talking to people. So that — I do miss the people in the audience and the fun: “I came with my mother! And this is my mother!” I miss that. I miss: “My cousin and I came all the way from….” I miss that. I don’t miss this — who is left to interview?

WWD: That’s true. You have interviewed everyone.
O.W.: The problem is, and even now, because I started doing this with “Next Chapter,” there’s nobody — try to think of somebody — who would be willing to do an interview on a regular basis that you can’t go and Google and find out what has happened to them in the past week. There’s nobody.

[Sitting nearby, Gayle King adds: “Not even past week — (in the last) 10 minutes.”]

O.W.: In the last 10 minutes. By the time you get the interview on and you get anybody to sit down and do an interview, everything about it — [snaps fingers] — it’s so instant. It’s over. Except for this. [Smiles.] There are only a few [interviews]. I wanted Bruce Jenner. Diane [Sawyer] got it. That’s great but there are few. There are only a few [interviews], but you’re not going to be able to think about it.

[King adds: “Except for this.”]

Except for this.

WWD: Except for this. Well, now that I got this, my career is over. Damn.

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