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 newsmagazine 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 special After 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.
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?
I said, “Get what you want. Get exactly what you want because now’s the time. And if you don’t get what you want, then make the next right move.” Even without me, she was going to do that. But that was my advice, and I actually called up her lawyer, Allen Grubman, and I said, “Allen, she should get what she wants.” And Allen goes, “What the F do you think I’m doing here? I said the same thing to her!” The negotiation was already happening before her R. Kelly interview.
Though that certainly gave her more leverage.
I know. I sent her a text saying, “Jesus looooves you.” But [the R. Kelly interview] could not have been better if I had done that myself. I think every interviewer thinks, “What would you have done in that moment?” And what she did was absolute perfection. I just thought that for this moment to happen at the time when she’s also in the middle of negotiations is unbelievable — but she’s always had that [gift]. One of my girls who is studying to be a journalist sent me a text saying, “Oh, Auntie Gayle, broadcasting goals.” And I said, “Not broadcasting goals, life goals. Your life goal [should be] to be able to be centered in the middle of whatever storm is showing up in your life.”
In your estimation, is the Time’s Up movement doing enough to truly empower women?
I am grounded in a spiritual sense of: Everything is happening just as it’s supposed to be happening. So the fact that it even exists, that there is an organization called Time’s Up that’s created for the empowerment and the emboldening of women is exactly where we’re supposed to be right now. And the new day on the horizon is actually here. That new day where because a waitress in Idaho or a factory worker in Michigan has heard somebody else share their story, she says, “Oh no, no, no, you can’t talk to me that way, I’m not going to take this anymore.” That’s happening all over the country, so the culture is changing because of the Time’s Up movement.
Take me back to your Golden Globes speech in 2018, when you first uttered those words, “A new day is on the horizon.” At what point on that stage did you become aware of your impact?
First of all, all I was thinking about every time somebody applauded, I was counting how many seconds it was because I’d been told that the speech was too long and I needed to cut it. That was what I was told during rehearsal.
Safe to assume you didn’t cut it?
I had said, “I don’t want to [rehearse] it in front of [everyone].” They said, “Well, can you just read it for time?” So the producer comes out after, and he says, “Darling, powerful. Very moving. You need to cut three minutes.” This was the morning of. The morning of! And I’m like, “What?” And then he said to me, “I know how much you care about your fellow colleagues, you’re going to be at the top of the hour where all the best actress and best actors are and I know you don’t want to take time away from them.”
Playing the guilt card …
Yeah, now it’s going to be my fault if other people don’t have the time. But I didn’t know how I could do it. I thought about taking out the whole story of the woman who died, Recy Taylor, but it doesn’t fit without her because that was my grounding space. So I didn’t cut it and I was scared the whole time. I’ve never had dry mouth in all of my speeches in all my life. I was panicked. So when people stood up, I was like, “Oh my God. One Mississippi, two Mississippi, oh my God. Four seconds. Five seconds. Sit down! Sit down!” And as I neared the end, I go, “They can’t cut me.” That’s all I’m thinking. “Don’t cut me.” But I didn’t obey the rules, and so I expected they would. When I walked off with Reese [Witherspoon], I went, “Oh my God, they didn’t cut me.”
If I’m not mistaken, some variation on #Oprah2020 began trending almost immediately.
We got into the back pressroom and they said, “You’re trending.” And this you’ll love: Originally, I was going to interview the Time’s Up women [for a CBS Sunday Morning segment] before the Globes, and my chief of staff, Amy Weinblum, said to me, “You know, you should probably wait and interview them the day after because something may happen [at the ceremony].” So I was waiting the whole time for something to happen. Every time somebody would get up, I’d go, “No, I don’t think that was it.” “No, that wasn’t it.” And then afterwards, she said, “You happened!” I was the thing that happened. (Laughs.)
I imagine you have spent a lot of your career as the only woman and the only black person in a lot of powerful rooms. In your experience, how does that impact the decisions being made?
Oh, for so many years, there wasn’t a brown person or another female in a 50-mile radius. I just sort of got used to it.
What happens when there’s only one?
It’s hard to be heard when there’s only one. I remember my friends would say — actually, people in college who were not my friends — would say, “Oh, you’re a token,” and I’d say, “Yes, but I’m a paid token and I’m going to use it.” It actually strengthened my resolve. Any time I’ve been in a situation where I felt marginalized or someone else was marginalized, I’ve used that information as what not to do. For example, when the Oprah show first went national, I went to the management at WLS-TV [the ABC-owned station in Chicago] — I won’t name names — and I said, “Everybody needs more money in this national show.” They said, direct quote, “Why do they need more money? They’re a bunch of girls.” I said, “Well, it’s a bunch of girls who are now doing a national show.” And they said, “They’re in the same room, with the same desks, and the same office, on the same street. They don’t need any more money.” So that first year I gave everybody bonuses. I had a big dinner and my idea of being creative was to have $10,000 rolled up in toilet paper rolls at the dinner as gifts because I couldn’t get management to pay them. Then I went to management and said, “If you don’t pay them, I’m not going to work.” By the next year, it was like, “I’m not going to keep paying them. I shouldn’t have to pay everybody out of my salary.” That informed me that if I ever get my own business, I’m going to pay people well.
When did you develop that confidence to push back?
I remember working in Baltimore [in the mid-1970s] and being in a position where I was doing the exact same job as my [male] co-host and going into my boss, saying, “Gee, I’d like to get a raise,” and them saying, “But why? Do you own your home? Do you have children? He has children. Do you have college payments? Do you have a mortgage?” I just tucked my tail between my legs and said, “Thank you very much.” And that’s when I decided I’m not going to become an institutional anchor. I’m going to leave here because they cannot see my value. But I didn’t blame myself for one minute. I just thought, “Oh, you don’t get it.” I always felt, even as a young reporter, that there was something more important to do and say than this thing I’m doing here right now, out here chasing ambulances. I could feel in the center of myself that my life was not going to be out on the street holding a microphone in front of people’s faces and every day looking for the worst thing that has happened to someone to report about. So there was that innate knowing that this is not going to be it. Through all of the times I felt discriminated against, put down, marginalized, I always thought, “It won’t be long.”
Looking ahead, what’s left on your bucket list?
No, it doesn’t feed me anymore.
Why not? Only a year ago, when you were starring in A Wrinkle in Time, I believe it still did.
Yeah. It did. I got fed. But I think to be really, really good at it, you’ve got to do it a lot. You’ve got to work at it. And it’s got to be something that you have true passion about. I don’t think it’s something you can dabble in. It was fun to be Mrs. Which, and I did that because I wanted to go to New Zealand and wear the costumes. But no, it doesn’t feed my soul anymore. I can’t imagine something coming along except … Oh, I can’t tell you because then when somebody else gets it they’ll know I was offered it [first]. But there was something that I was offered on Broadway — Scott Rudin sent me a letter and said, “You should take this role,” and it was really, really tempting.
When we sat down a few years ago, you were interested in the idea of returning to Broadway.
I’ve wanted to do it. But then this is what I did. On one of my visits to New York, I actually put myself in the space of: You live in the city now and this is your corner and this is where you walk your dogs. Are you only going to bring one dog or are you going to bring all the dogs? This is where you’re going to go to get groceries. This is your dry cleaner. How are you going to feel being in this city without trees and grass? So I put myself in the future and walked myself through it, and I thought, “I can do it for a month, I can’t do it for six.” I am enhanced and fulfilled by my association with nature. I have this whole crazy-ass routine [in Santa Barbara]. It’s only after I get up to pee after 3:30 a.m. that I will hit the blackout [shades] so that the sun doesn’t wake me up because then I get to see all the benefits of the night. [I get to] see the moonlight on the ocean. Then I have the morning ritual where I hit the shades and I just wait to see what the day is. Every day I go, “Look at you, day. Look at you!” That’s not going to happen here [in New York].
Two years ago, you told my colleague during a podcast that the last time you flew commercial was in the early ’90s and that you can’t remember the last time a person didn’t immediately recognize you. I was struck by both answers, and I’m curious: When was the last time you genuinely missed your anonymity and what’s the first thing you’d do if you could have it back?
What a waste of time! This is the way it is. I have accepted it.
But if you could go anywhere, do anything?
But I do.
Yeah. There’s not one thing that I would want to do. Except now I think about going to a party if people have their cameras at the party. Because a party with people with their cameras is not really a party for me. You’re on display and you’re just literally selfie-ing the night away. And if you do one, you’ve got to do every one. But you have to know this about me with all the times we’ve talked — I’d be the same person if I was the fourth grade teacher that I thought I was going to be.
I do, but I also know that there is something nice about being able to run across the street to get a cup of coffee when I want it.
Oh, I do all that stuff. And now there’s kind of this respectful arm’s length. When I was on TV every day, it was like, “Hey, Oprah!” But now, it’s this respectful, “Oh, it’s you” kind of thing. Unless it’s … you know, I was at Apple the other day, and this young girl just started shaking and crying. She said, “But you don’t understand.” I just took her by the arms and I said, “Are you OK?” And she said, “You don’t understand.” I go, “Yeah, I do.” She goes, “No, but you don’t.” I go, “Yeah, I do. I raised you. You came home from school and there was nobody home, right? Every day, four o’clock, I was there.” “Yes, yes, you raised me.” That warms my heart. There’s a whole generation of people who are, like, 30, and that was their life. And now I [also] get “My mom loves you,” and I go, “And you don’t?”
I was impressed by the fact that you knew the exact month, April 1991, that you took your last commercial flight. Tell me about that day.
I was going to an award ceremony for Aretha Franklin, and I was in the airport and I was leaned over like this (puts her head between her knees) and a woman came up to me and said, “You’re not acting like you do on TV.” And I go, “I’m just here.” And she says, “Oh, I see you. Trying to be incognito.” And I say, “No, ma’am.” She says, ” ‘Cause on TV you always giving people hugs. I want a hug.” So I stood up and I gave her a hug and then I went to the phone and called my lawyer and I said, “I’m going to do it, I’m going to get the plane. This is going to be my last time waiting four hours in the Chicago O’Hare Airport.”
Yeah. And nobody likes to mention this name now, but I had multiple conversations with Bill Cosby about getting a plane. I was trying to justify it, like, “OK, if I put 10 people on the plane, that would’ve been how many airfares would I have to pay for?” And he said, “You’ll never be able to justify it because it’s a true luxury. You can make a decision that you’re going to take the leap and do it or not, but you’ll never be able to justify the expense.” Which is true. [So, I took a] leap of faith and I wrote that first check — because I can’t stand bills — for my first G4 for the full $25 million. I remember I had seen Camille Cosby at Teterboro when I was chartering a plane and trying to justify it. Someone said, “Oh, Mrs. Cosby is over there, would you like to say hello?” So I get on Mrs. Cosby’s plane and Mrs. Cosby is on the plane with a pair of overalls and diamond stud earrings and she’s on her way somewhere to work on her doctorate and I said, “Where is everybody?” And she said, “There’s only me.” I said, “You’re going to use this whole plane?” And she said, “I’m worth it.” Just like that. And I went, “Well, if she’s worth it, maybe I’m worth it.”
Interview edited for length and clarity.
This story first appeared in the April 30 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.