How Oprah Winfrey, Reese Witherspoon, and Mindy Kaling Overcame Their Own Insecurities

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Photo: Jesse Grant/Getty Images for Disney

In the new film A Wrinkle in Time, director Ava DuVernay sends her young protagonist Meg Murry on a planet-hopping adventure with the help of three mysterious astral travelers — Mrs. Which (Oprah Winfrey), Mrs. Whatsit (Reese Witherspoon), and Mrs. Who (Mindy Kaling) — yet the most important journey for Meg is an intimate one: She must conquer self-doubt to realize her full potential. When Vulture recently sat down with Winfrey, Witherspoon, and Kaling, then, it struck us that these three enormously successful women have career paths that are every bit as dazzling and unlikely as Meg’s leap from Earth to Camazotz, but that they, too, must have faced their own fears somewhere along the way in order to get as far as they have. So we talked about it.

Oprah, what was the biggest example of you overcoming a personal insecurity to succeed?
Oprah Winfrey: For me, it was that I could be a better Oprah than a pretend Barbara Walters. I was pretending to speak in a certain way that I thought was what you’re supposed to do when the camera comes on, and that was not going to lead me to what eventually happened with the talk show.

When did that click for you?
OW: I was doing the news one evening and I had this crazy-ass habit of not reading the copy ahead of time, ’cause I wanted to be spontaneous. I wanted it to feel like, “Oh, six people in a pileup on the 95 today, isn’t that something?” So, that evening, I mispronounced a series of names: I was rolling my Rs for “Rio de Janeiro,” and I pronounced Canada as “Ca-NAH-da,” because I was trying so hard to be like Barbara Walters. I said, “Ca-NAH-da,” then, “… oh, that’s Canada,” and I cracked myself up on the air.

That one little piece of being able to break the veil between being on air and not, it let a little piece of myself through, and I couldn’t stop laughing on camera. And the audience in Nashville WLAC-TV, channel 5, responded to it, and I started being more of myself. Trusting that was the big breakthrough for me. I created a career where I’m being paid to be myself.

Reese, what was the biggest thing you had to conquer?
Reese Witherspoon: The lack of representation of women in film. It was driving me crazy — I was seething angry about it all the time — and then I started articulating it and saying it more out loud to people, particularly my husband. I was like, “What is this? There’s no [parts for] women, and there’s no female directors, and I just don’t get it.” And he said, “You know, nobody reads more books than you.” He represents actors, and he was like, “Let me tell you something: You read the script the day you get it, and nobody else does that. Why don’t you just produce your own movies, honey?” And it just didn’t occur to me that I could do it.

He said, “If you want to make different kinds of movies, you have to put your money where your mouth is. Spend your own money, start your own thing, and find a new way to get things to the marketplace that isn’t going to go through all the studio notes that cut the truth about women out. Invent a new development process where you just deliver the product, and it’s ready to go, and you say, ‘We’re making it, and this is how we’re making it, and we’re not changing a word.’”

OW: “Do you want it? If you don’t, we’ll take it somewhere else.”

RW: And wow, people are like, “Thank you for doing this!” They don’t say, “No, we don’t want that product,” they’re like, “We don’t have the time or money  to invest in that ourselves, but we’re so glad you’re investing in that and we want to buy that product.” So it was big for me to overcome the idea that I’d have to spend my own money and run my own company. I didn’t know if it was going to be successful or not, and being responsible for a staff of people … that’s terrifying to me, that I might have to turn to them one day and go, “This didn’t work, guys.” But you have to try. You have to try.

Mindy, was there something internal you had to deal with to become successful?
Mindy Kaling: I think I had to stop looking for any kind of representation of myself in TV. You know, I came out in 2004, and there was no one who looked like me when it came to comedy writers. They all looked exactly the same, and there was no one that even had passing resemblance to me. I didn’t remember even seeing any young African-American or other Asian comedy writers … I was in an all-white, male room. Over the past five years and then a lot in the past six months, there’s now people saying that is not okay. Now, I’m more likely than not to see a story starring a young minority woman, which is really exciting, because you could go a whole lifetime and not have any of that happen.

What would it have meant to you to see an Indian actress in a film like A Wrinkle in Time?
MK: That’s why doing this movie is incredible. Science fiction and fantasy are genres that I’ve loved since I was a kid — I made sure that I watched Star Trek: The Next Generation every week — and it is a genre that did not love me back. It is a true love, because I still loved it no matter what, but they did not care.

OW: They did not care about Indian girls.

MK: They do not care about Indian girls watching. It’s so crazy to have these genres where they can imagine whole planets and civilizations and worlds, with crazy hair and makeup and costumes and creatures, but they cannot imagine that anybody but a white person would ever be on the show.

OW: Isn’t that an incredible thought?

RW: That’s a limited imagination. Why are they all white? Why is there one woman in all the [original] Star Wars movies? Who gave birth to all those aliens? Where are their mothers, their sisters, and their friends?

It reminds me of what Carl Sagan said on The Tonight Show when the first Star Wars came out: “They’re all white … not even the other colors represented on the Earth are present, much less greens and blues and purples and oranges.”
OW: I didn’t know Carl Sagan said that! That’s pretty interesting.

RW: Yeah, it’s very astute.

MK: This is what’s amazing about this movie, the reinterpretation of the Mrses. who were not described as we are. Every place where Ava could have decided to go the more conventional, safer route, she didn’t, which is why it’s so exciting to be part of it. To think about what the younger version of me would be thinking if she watched it …Oprah always talks about how everybody just wants to be seen, you know.

Black Panther doing phenomenally well is a testament to that.
OW: Oh, absolutely, that’s what that is.

Reese, you’ve been developing new TV shows to star actresses like Octavia Spencer and Kristen Wiig. Was there a point where you felt your own personal ambition wasn’t enough?
RW: I’ve done enough for myself. I had a whole great career, I won every award I can win … well, except for maybe a couple. But I don’t feel anything from awards. It doesn’t make me feel like I’m doing anything that’s going to change the culture or leave this business a better place if I’m not doing more for other people. I’m using everything I’ve learned along the way, and my own money and celebrity collateral — whatever that is — and I will stand next to anyone I believe in that deserves a different opportunity. And that’s thrilling to me! I wake up every day and I turn to my assistant and go, “I love this company.” I walk in the door and I’m like, “What are we going to do today? Where are we going to dream? Who could we have? What are we doing?” It’s changed my whole life, in such a good way.

OW: Has it enhanced or fortified your acting? What has it done to that part of you? [Winfrey turns to Vulture.] I’m sorry, I’m asking your question.

That’s a great question, though. Go ahead, Oprah! 
OW: Do you feel a difference in your acting?

RW: I don’t worry about the acting.

OW: Interesting.

RW: And this is going to sound like I’m not being humble, but I know I conquered that wall.

OW: Mm-hmm.

RW: I did comedies, and it was good, and I did some dramas, and people liked those, but that doesn’t change the way people see themselves. I know the power of movies. I’ve traveled the whole world, I’ll go to China, I’ll go to Australia. I was in a fishing village in Belize where people came running out with this movie I did — it wasn’t even a very good movie — and they were holding it, going, “Reese, Reese, we love this movie!” I know the power of storytelling, I know what I have, and I know how I can use it to help people.

Mindy, when you were promoting Inside Out, you said that you very rarely get asked to play roles you didn’t create yourself. What does it mean to you when A Wrinkle in Time and Ocean’s Eight invite you to the party?
MK: It’s a turning point. It’s an uncomfortable feeling, actually, when you’ve been so seminal to creating all the roles for you — because no one would ever do it except for you — and then you have to step back as an actor and relinquish control. It’s hard when you’re sitting in the trailer as an actor and not as the person who is putting everything together, but then once you do, and you’re in the visionary hands of someone like Ava DuVernay, it actually doesn’t get better than that. It’s the same with Pete Docter for Inside Out, or a franchise like Ocean’s, and I’m still getting used to it. You know, I can’t believe that some people were blessed to be able to do this in their early 20s, so I don’t take it for granted.

OW: Mm-hmm.

MK: I mean, I look at our faces on this [Wrinkle in Time] poster, and I’m like, “Zach Galifianakis’s face isn’t even on this poster, and he’s one of the greatest living funny humans.” This cast is unbelievable, and so I feel so much gratitude for it. It’s exciting to not have to create this myself — and by the way, I speak for all of us, because we’re used to having to do that. [Wrinkle] is great because Ava was the one who did it, and she just invited us.

Oprah, what was your journey to being able to ask for what you’re worth?
OW: Ooh.

RW: Oh, that’s a good question.

OW: Oh boy, I didn’t expect anything this good this late in the day. My journey to asking for what I was worth? Okay, let me sit up for that. I wanted to do The Color Purple more than anything else in my lifetime. I’ve never wanted anything as much since, but I was at ABC at the time, and I only had two weeks’ vacation. I had a contract that said I would get three weeks the next year, and then four weeks by the third year, so I begged my bosses, “If you just let me do this film, I will not take another vacation for the next three years. I will use the next two years’ vacation to compensate for that.”

And my lawyer at the time, Jeffrey Jacobs, said, “You never want to be in a position where you have to beg and give up your vacation time and sacrifice for something that really means something to you. So why not approach them with the idea of ownership?” And I was like, “How are you going to do that? How am I going to own it?” And he said, “Well, you have to believe that you’re worth the risk. If it doesn’t work, you lose, but if you actually, really believe that it’s going to work, you win big.”

MK: Wow, wow.

RW: Wow.

OW: So I said I would rather own myself and take the risk of losing everything. You could lose big, but you could also win big. You own yourself. You own yourself! And that choice changed everything for me.

How Oprah, Reese, and Mindy Overcame Their Own Insecurities