Oprah Talks Apple Plans, ’60 Minutes’ Exit, 2020 Election, Her Creative Fire, and More in Exclusive Interview for The Hollywood Reporter’s Empowerment Issue

Photo credit: Ruven Afanador

What’s left for the media empress and icon of inspiration? In a wide ranging interview, Winfrey explains her streaming strategy (including a possible interview series), who she’s eyeing for 2020 (“I’d like to see what’s up with Butta” — aka Pete Buttigieg) and the creative fire that fuels her now.

The year was 1984. Oprah Winfrey was making her way to the Hotel Bel-Air for the first time. As she weaved up Stone Canyon Road, the once impoverished talk show host from rural Mississippi was mesmerized by the opulence tucked behind towering gates.

“It’s the first time that I actually realized how rich white people really lived,” she says. Being able to see it, firsthand, was transformative. “Just recognizing that there is another way of living let me know that that is possible.”

Her series of aha moments continued. The following year, Winfrey arrived at the offices of Steven Spielberg, for whom she made her film debut in The Color Purple. The role earned her an Oscar nomination and an invite to his Amblin headquarters in L.A. Until that moment, Winfrey had no idea, she says, that “you could have your own studio.”

More than three decades later, Winfrey is a self-made billionaire (Forbes estimates her net worth at $2.8 billion) with lavish homes tucked behind gates and, yes, her own studio. She has a TV network, too, along with an eponymous magazine and a megadeal with Apple that will include a book club, documentaries and — she teases here — a potential series that would put her back in the interviewing chair. She’s also parlayed her iconic status into opportunities to educate and inspire worldwide. “I want to leave this planet being able to say, ‘Caused no harm, did a lot of good,’ ” she says.

As Winfrey, 65, prepared to receive The Hollywood Reporter‘s first Empowerment in Entertainment Award at an April 30 gala, she invited THR to her hotel suite in Manhattan, where she was promoting her latest book, The Path Made Clear. Relaxed in designer sweats and black-rimmed glasses, Winfrey opened up about her political plans, her 60 Minutes departure and how a history of marginalization ultimately shaped her.

What do you know about American politics now that you didn’t on the day Trump was sworn in?

I know that there is an underlying level of discontent and dissatisfaction that was stronger than anything I could’ve imagined. Had I been doing the Oprah show at the time of the 2016 election, I wouldn’t have been the least bit surprised by the outcome because every day that audience was my focus group on the world — every day they came from red states and blue states with every kind of belief system, gathered together in this communal moment of the Oprah show. And the best time for me was not the show but after the show, talking to all those people. So I would’ve known and felt and heard it in a different way and I would not have been surprised on election night.

Armed with that information, what would you have done differently?

It’s all backseat driving now, but I would’ve applied what I was hearing to the kinds of shows that we were doing. I would’ve brought whatever that was into the forefront in a way that the polls couldn’t do or weekly news-magazine shows can’t do. I wouldn’t have been like, “Whoa, I didn’t know everyone was that mad.”

You have so much cultural power. Short of running yourself in 2020 …

(Shakes her head no.)

… how do you use it?

Right now, I’m studying the field. I’m reading Shortest Way Home by [Pete Buttigieg], I call him Buttabeep, Buttaboop. (Laughs.) The name’s either going to really hurt or [really help] — I think it’s going to help, actually. Just the other day, I was at Apple with Spielberg and we were in the hallway talking about, (employing a dramatic voice) “What are we going to do?” And I said, “Have you heard of this Butta guy?” He goes, “No, Butta-who?” I go, “Buttabeep, Buttaboop. Look him up.”

“Mayor Pete” feels easier.

I like saying “Butta.” (Laughs.) So I’m reading about him. I have Kamala’s book. I just got the Vanity Fair piece on Beto [O’Rourke]. I’d done some research background stuff on him before. I already know Cory [Booker]. So I’m quietly figuring out where I’m going to use my voice in support.

There’s a line in the Vanity Fair Beto piece that says, “Oprah Winfrey, who helped anoint Barack Obama in 2008, practically begged him to run at an event in New York City at the beginning of February.” Is that true?

Oh, I do not think I practically begged him. When I read that, I thought, “That’s not accurate.” What I was practically begging for is, “Will you tell me if you’re going to [run] in this moment right now?” Even backstage, I was saying, “Well, when you are going to do it, will you let me know you’re going to do it?” Which he did not. So I’m sitting back, waiting to see. It’ll be very clear who I’m supporting.

Trump has demonstrated how entertainment can be used to advance noxious causes. How do progressive creatives make things that have a positive influence but don’t feel like after-school specials?

After-school specials? Oh my god, I think I actually did one. (Laughs.) I think with the spectrum of streaming services and [other channels], a lot of people are doing it now, and it’s not after-school specials. TV is so good these days. I don’t watch a lot because I have to watch a lot on my own channel, so the only other thing I watch is The Crown, and it’s so good. I heard they just found a new Diana. The fact that I even know that …

I remember talking to you when you were launching OWN and you had big plans for spiritual programming …

Oh yes, I was delusional. Somebody please take me out of my delusional spiritual closet.

In today’s landscape, with the Apples and Netflixes that you referenced, is there space for that type of programming in a way there wasn’t then?

This is what I learned from that experience. And, oh boy, was that a hard lesson. You have to meet the people where they are, not where [you are]. Not everybody wants to sit up and talk Eckhart Tolle all day. I do. I can have him to dinner every night, but not everybody else wants to do that. So, I got that.

That brings me to Obama’s foray into producing. What are the opportunities for him and Michelle at Netflix, and what are the pitfalls?

Oh, they can do any damn thing they want.

What advice have you offered?

When they were starting, he called me for names to run [their company], and I offered him some. They ultimately were not the people he chose, but that’s fine. There’s nobody like them. Nobody. Their desire to want to use this medium to tell stories, to show us our history, to bring an informational, inspirational approach to content — I’m looking forward to seeing whatever that’s going to be.

You factored prominently into Apple’s first programming presentation in late March. What will you do for them that you can’t do at OWN?

Apple exposes you to a whole lot more people. The thing that I’m really, really excited about — as I said that day — is creating the world’s largest book club. And if I want to do a film or a doc series … The best place for [my docuseries on mental health] is not on OWN. Because you don’t have the bandwidth and you have to create a completely different audience and then you have to have marketing.

One of your other Apple projects will be about sexual abuse in the workplace. If you’re successful, what will you have revealed?

My mission is always about letting other people know, “You’re not alone.” Obviously, we’re going to do the women in Hollywood and in the music business, but what was important to me was to be inclusive of waitresses and factory workers and nurses and nuns and people who you’d never imagine, so that the world can see themselves in their stories. I’ve been adamant that if you only tell the Hollywood story, you can only be partially heard.

Why is that?

Because, I think, there’s a feeling in the zeitgeist of, “Well, OK, that’s Hollywood, they ask for it because they wanted to be in this industry and we’ve always heard of the casting couch.” So my hope is that people will understand what a massive problem it is and that it’s pervasive — and be empowered by listening to other people’s stories about what they were able to do. It’s the shame, the guilt, the keeping the secret to yourself that then informs all of your choices and changes who you are. Most women blame themselves.

What else do you want to tackle as part of the Apple collaboration?

I don’t want to be in a daily rhythm of trying to come up with people to interview, but when there are people who are of the culture — like, last year, I would’ve wanted to sit down and have a conversation with Christine Blasey Ford. Right now, I’d probably want to sit down and talk to Butta.

I knew it was coming back to Butta.

I’d like to see what’s up with Butta. (Laughs.)And then whatever else shows up. Having experienced such devastation in our own community in Santa Barbara [from deadly 2018 mudslides near her Montecito home] and recognizing what happens once the news cameras go away — we were on the news for a couple of days, but people would come to my house [long after] and go, “Oh my god, this is still going on?” Yes, we lost 21 people, and two are still missing. I was cleaning out 154 trucks of mud months later from my backyard. And so … I think a lot about the people of Paradise [in fire-ravaged Northern California]. Really, I wake up in the morning and think about those people. I want to talk to them. I want to see how they are and remind people that the rebuilding of a life takes time.

Do you foresee this as one-offs or a series?

Maybe at some point there will be a regular series.

You made a lot of noise by getting involved with Leaving Neverland, via your specialAfter Neverland. How did that come about?

I didn’t even have to be in it. I didn’t have to take on all that. I said to myself the other day, “Why did I do that?”

Do you regret it?

No, I don’t regret it. It wasn’t really regret, it was just … actually, I was having dinner with friends and they were saying, “We saw you were in that.” Like, “Why did you do that?” This is what happened. I saw it, and I was shaken by it. I wasn’t even shaken by the fact that it was Michael Jackson, I was shaken by the fact that [filmmaker] Dan Reed had done a really good job of showing the pattern, and for years, I had been trying to show people the pattern. I’d been trying to say it’s not about the moment, it’s about the seduction. The first thing I said to Gayle [King] when we watched it was, “Gayle, you’ve got to get those guys [on CBS This Morning].” She Instagrammed about it, and I go, “No, you shouldn’t Instagram, you should just get those guys.”

How did you get involved?

I sent [HBO’s former chairman Richard] Plepler a text and said, “Look, I’m trying to reach some of your people. What are you all doing with this?” I really wanted to talk to not just the guys but other people who were seeing it because I knew that people were going to be triggered by it. I knew that there would be people who would be re-traumatized by it and would see themselves in it, and I thought, “I can help thread the needle of what is actually happening here.”

I assume you hadn’t anticipated the blowback?

Oh, the hateration? Honeeeeey, I haven’t had that much hateration since “The Puppy Episode” with Ellen [Winfrey guested as the therapist on the 1997 Ellen sitcom episode in which Ellen DeGeneres’ character comes out], and it made me think, “Thank goodness Ellen’s coming out was before social media because can you imagine?” During “The Puppy Episode,” I had to take the people who were on my switchboard at Harpo off the switchboard because of the vitriol. They were scared.

What were people saying about that episode?

The N-word, “Go back to Africa,” slut, hoes. … It became racist and homophobic and vile and “String ya up,” “It’s against the Lord.” I mean, you name it. Similar to the Michael Jackson thing. I happened to be on Twitter for something, and somebody had said, “Oprah Winfrey is a disgrace to the race” or something. Yeah, the whole race. I decided, you know what? This isn’t going to be healthy for me, so I just didn’t engage with it.

Did you hear from any of the Jackson family?

(Shakes head no.) Because for me it wasn’t even about Michael Jackson. It was about the bigger issue.

Let’s talk about the cultural reckoning that’s going on. One of your 86 jobs is at 60 Minutes, which has been rocked by its share of #MeToo incidents …

I’m no longer doing that. I’ve removed myself from that, so I have only 85 jobs now.

I hadn’t realized. How come?

I’d actually gone to [former 60 Minutes executive producer] Jeff Fager prior to the whole CBS (pantomimes an explosion) and said I was going to be working with Apple and that it didn’t mean I would never do something [with 60 Minutes] but I would probably be taking all of my energies and putting them into whatever I wanted to do at Apple. It was an interesting experience for me. I enjoyed working with the teams, and I’m probably going to work with some of the freelance people on my Apple stuff, but it was not the best format for me.

Why not?

How should I say this? Never a good thing when I have to practice saying my name and have to be told that I have too much emotion in my name.

I take it that didn’t sit very well with you?

No, it’s not that it didn’t sit very well. I did it. I think I did seven takes on just my name because it was “too emotional.” I go, “Is the too much emotion in the ‘Oprah’ part or the ‘Winfrey’ part?” I had a deja vu moment because I’ve actually lived through this once before when I covered a story as a young reporter [where] the family had lost their home and my boss told me that I reported it with too much emotion. I had too much emotion in the story. I thought, “OK, so you’re not supposed to be involved in the story, I get that. You’re a journalist.” But the same thing is true even with a read [at 60 Minutes]. They would say, “All right, you need to flatten out your voice, there’s too much emotion in your voice.” So I was working on pulling myself down and flattening out my personality — which, for me, is actually not such a good thing.

Gayle has made the choice to stay at CBS News. What advice did you give her during what became a very high-profile negotiation?

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SOURCE: The Hollywood Reporter – Lacey Rose