Exclusive: Oprah on last 25 years

Twenty-five years after The Oprah Winfrey Show debuted, the game-changing daytime smash comes to an end as the talk legend reflects candidly on her legacy, how she makes decisions and why her voice used to be higher.

Roger Ebert helped you start the show. How?
Roger and I went out on a date, believe it or not, and he said his company [King World] was interested in talking to me about syndication. I said, “Ehh, I’ve done that already.” In Baltimore, we did this show called People Are Talking and it was syndicated and nothing happened; I had a syndication contract that granted me $10,000 extra if we signed 20 stations, $50,000 if you got 100 — and if I got all the markets, I was going to get $100,000! That was a contract with Westinghouse. I still have it in my bag. Aren’t I glad that didn’t work out?

The new show certainly did. How strategic were you in getting it to work so quickly?
If I ever write a book, people would be astounded at how naive and unsophisticated I was. Back in the early ’90s, I saw an article in USA Today where Larry King said he wished he had my publicist. I laughed because my publicist was the intern on [my previous show] AM Chicago. I asked, would she help me with the mail? I was going to pay her $1 a letter, then I started getting so much mail, I couldn’t pay her anymore. She said, “Well, I can be your publicist.” We’d get all these offers from magazines, and she’d say: ‘Good Housekeeping called. My mom says you should do it because they have the seal of approval.’

Were you nervous?
I was, and I used to break out in hives under my armpits — even when I didn’t think I was nervous, I would break out. I remember [the very first show] and that burgundy schmatta outfit I was wearing. You can tell I was nervous: My voice gets higher-pitched. Somebody on Twitter the other day said: “Oprah, what happened to your voice? I don’t recognize your voice from the past.” I guess it’s a level of maturity and confidence.

What was the biggest challenge of launching the show?
We tried and tried to get stars, and nobody would come on. It’s like, “Who are you?” People would say, “Ofrie, Okrah, what?” My real name is Orpah. Thank goodness that got screwed up [when Winfrey’s family pronounced it “Oprah”]. It’s just an awful sound, “Orpah.” The first show featured an unknown woman who guaranteed you on finding the perfect mate. People immediately responded to the message we were trying to bring. I recently was looking at the tape, and in that first five minutes I state what the intention is. I say, “We wanted to do the show for you because we wanted you to know that you’re not alone.” All the things I envisioned the show to be happened.

Is there one guest who most stands out?
My all-time favorite is a woman named Tererai Trent. She was born in Zimbabwe in a village and was 11 years old and married and had three children by the time she was 18 and had buried her dream in a tin can under a rock. And the dream was to come to America and get an education, and she just finished her Ph.D. last year. To me, that story expresses hope and perseverance — never giving up, believing in yourself. It symbolizes and epitomizes everything I’ve tried to say on this show for 25 years.

When did you first think of ending the show?
I started thinking of ending it with the 20th year because I get hung up on numbers; it’s a little OCD. I always like even numbers and solid numbers, because I grew up with a father who would say, when I would ask him, “Can I have some money?” He’d say, “Sorry, my money’s not even.” So I started thinking about it seriously for the 20th anniversary. And then Mattie Stepanek, a little 12-year-old boy with muscular dystrophy, sent me a letter from his hospital bed giving me all the reasons why I should wait until 25. That was a huge influence on me. [In 2007] Jerry Seinfeld said to me, “It’s yours to design, Oprah.” That’s when I seriously started thinking: “I have allowed the success of it to dominate my entire life. The more successful it gets, the more you have to keep raising the bar.”

Do you go to anyone for advice about big decisions like that?
First, I go inside myself. If whatever people say isn’t in alignment with what I’m thinking, rarely do I make the mistake where I believe other people’s opinions are more valuable than my own when it comes to decisions about myself. But I turn to [partner] Stedman Graham, [best friend] Gayle King, [personal trainer] Bob Greene, Tyler Perry.

Do you feel emotional now that the show’s ending?
You know, Tyler’s been calling me every day as though I’m ill! I keep asking, “Is there something wrong with me that I’m not that emotional?” Everybody all around me for the past 20 shows has been so emotional. I had one weepy moment after [taping] my final real show the other day with my all-time favorite guests. I’m emotional in that I feel a sense of relief and completion that this effort was well done. I feel really great about that. I have not one single regret.

Not even about having James Frey as a guest, when you later learned that he embellished his memoir, A Million Little Pieces?
[Spiritual writer] Eckhart Tolle shifted my thinking about what the ego is. That was life-transforming. I was able to call Frey [who made a return appearance and was berated by Winfrey] and apologize.

And you brought him back for one of your last shows.
I was trying to make a decision [about something else] and in my head a voice said, “Don’t make the same mistake that you made with James Frey; don’t rule with your ego.” What I realized from Eckhart Tolle is that any time you put yourself in a position where you’re trying to make somebody prove something or demanding that they show you respect, that’s your ego ruling. I’ve talked to women who put their children in the freezer and killed them. I talked to murderers, to child molesters, and I’ve always been open and not judgmental. That’s the difference: I just want to open myself to hear what happened, and I didn’t do that with James Frey.

You said you have no regrets. What about the problems that took place at your school in South Africa, the Oprah Winfrey Leadership Academy for Girls?
I regret that I didn’t take the time to build the infrastructure first. But I learned a big lesson from that: Schools aren’t about bricks and mortar. It’s not worth rushing ahead without the infrastructure in place. You’re nowhere without strong leadership.

Speaking of which, where do you stand in replacing former OWN CEO Christina Norman?
Peter Liguori, who is the COO of all Discovery channels, is interim CEO. I’m going to take my time and find the person, or persons — I’m now thinking it’s not just one person — who are best in alignment with the vision we want to push. One of the lessons I learned from my school is that the same person it takes to build a school isn’t the same person to carry on the school. I’m extremely grateful to Christina and her sacrifice for getting it launched. Now we’re on to the next level.

Will you resurrect your talk show there?
In its current form, no. I want to be clear that I’m not ending my career in television; that would be foolish and I’d be miserable. The new way of communicating with people isn’t just through television. I intend to use every platform to stay in touch.

Growing up, is this the way you imagined your life?
I imagined that I was going to be the world’s greatest teacher. And, you know, as I move into these final days of Oprah, it feels like this platform has been a great teaching and learning experience, both giving and taking from the audience. It feels like the world became the classroom.
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