Reese Witherspoon

Reese Witherspoon Isn't Afraid to Say She's the Best

With her recent nine-figure money moves and a full slate of upcoming projects, the Morning Show star is like the Lebron James of Hollywood — and she’ll be the first to tell you.

They share a mutual pal in Oprah Winfrey, but "we don't have a great meet-cute story," jokes Gayle King about her initial introduction to Reese Witherspoon. Over the years, they have gotten to know each other through corporate gatherings, private dinners, and, of course, regular interviews. (In 2019, King was even the subject as Witherspoon and her Morning Show co-star Jennifer Aniston were the ones asking the questions for a CBS Mornings segment.) When it was revealed this past summer that Witherspoon had sold her female-focused production company, Hello Sunshine, for around $900 million, King was among the first to salute her. "That was a big friggin' deal," said King during this talk for InStyle. "When I read it in the paper, I stood up and gave you a round of applause."

Gayle King: What's it like to be a badass? Own it, Reese!

Reese Witherspoon: I've said this to Oprah before, but LeBron James doesn't go, "I'm kinda sorta good at basketball." He's like, "I'm the best there ever was." So, yes, I do think I'm very good at what I do. I've been doing it for 30 years. I know what I'm doing. Give me the ball.

GK: You raise such a good point. Men never shy away from saying "Yep, I'm good," and women are always like, "Oh, thanks."

RW: Another important difference is that women have humility. I have no problem saying to people, "I don't understand what you're saying, can you please explain it to me?" Self-doubt is a good tool. You shouldn't know everything. Turn to somebody, but advocate to learn more and do better.

GK: Yeah, so many people, women especially, don't want to think they're not smart or that they don't understand. You don't have a problem with that.

RW: I've dealt with those types of biases for a long time in our business. Actresses, they're infantilized. People don't talk to them about money or deals; they say, "Oh, don't worry about that, we have that." Not empowering someone with information is a form of control. So at a certain point in my career, I kind of took back the reins. I finally picked up the phone and said, "I'm not excited about this one part of my deal," and my agent was like, "Well, let's change it." Sometimes you have to pick up the phone. Don't assume. You don't know the answers.

Reese Witherspoon
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GK: And sometimes, what's in print can be totally misconstrued. You were recently on the cover of the Time 100 Most Influential Companies issue, and the article says you've transformed your role in Hollywood from movie star to business leader. Was that your intention when you started Hello Sunshine [in 2016]?

RW: It was right about the age of 34 when I really started to look around my business and saw a lack of female leadership at the top, top levels. Women were not in decision-making positions, whether it was a green-light committee on a studio or owning their own media companies. You can look at Oprah and Ellen [DeGeneres], but beyond that, I'm hard-pressed to think of a woman who owns a very robust media enterprise.

GK: Ava DuVernay. We can put Ava DuVernay.

RW: Ava DuVernay, yes. And I think there's a whole lot of other women who are doing incredible work — Mindy Kaling, Lena Waithe, Kerry Washington. Basically, women should be in a place where they are very prolific in every aspect of the industry, not just acting.

GK: Not only have you started a thriving company, but it was widely reported that you sold it for just under a billion dollars. Is that the number you wanted? Or did you have to negotiate?

RW: Oh my gosh, yes! It was two, maybe three months of negotiations on the phone all day. Calls at one o'clock in the morning. I didn't know a lot about private equity. I'd never sold a company in my life. [Witherspoon and Hello Sunshine's CEO Sarah Harden will continue to oversee day-to-day operations and remain significant equity holders.] I learned so much. I was really clear about what women's stories mean in a marketplace. So it had to be a number that signified that it's big business because women are big business. Female audiences are big business. Female filmmakers are big business. You can't ignore half of the population of the world and say that they don't economically matter; they do.

GK: I like that after two months of negotiations, that final number had a whole lot of zeros. What was it like for you to get the check? Did you go home and say to [your husband] Jim [Toth], "Holy shit, look what has happened?"?

RW: I cried. I cried, and I thought about my grandma, and I cried more. I thought about all of the women who haven't gotten these opportunities, and I just feel really lucky that I'm standing in a path that other women created for me. [Starts crying] Sorry.

Reese Witherspoon
Gap shirt. Chanel pants and suspenders. Bulgari necklace (top). Almasika necklace. Cult Gaia pumps. Beauty Beat: Use a super smooth pencil, such as the MAC Cosmetics Eye Kohl in Teddy ($19), across your lash line for a subtle smoky effect.
| Credit: Emma Summerton/Dawes+Co

GK: Reese, I'm not trying to make you cry, but I was so proud and so happy for you.

RW: Thank you. I grew up in a military family, so it's about how you serve others. This is the way I do it. By hopefully making art more equitable and accessible.

GK: Yeah, but you got to call your mom, though.

RW: I did! The thing that's great about my mom is she's like, "That's nice, honey. Can I come over for dinner? And I don't eat fish." She just loves that I'm happy. That's all that matters to her. Success and monetary success, they're great, but she knows the real things in life that make you happy are family and a sense of giving back. That's the real metric of success.

GK: And we can tell what your family means to you. Your husband, your three children

RW: My first, most important priority is my kids. If I told you how much space in my brain they take up every day — do you even think they know, Gayle? I don't even think they know.

GK: No, they don't. People always love watching you and Ava together, because, honestly, nobody can deny that she is your daughter. Do you enjoy the reactions you get from people when they see you two together on social media?

RW: Well, I love being mistaken for her because it makes me feel so young. I'm so proud of her. She really rolls with it. I'm sure it's not easy looking exactly like your mother.

GK: Reese, stop it! When Mama looks like you, it's very easy.

RW: Oh, you're sweet! We talk to Zoë Kravitz a lot. Because she and her mother [Lisa Bonet] look exactly alike, so whenever Ava is frustrated, I go, "Call Zoë, text Zoë, she knows what to talk about." I mean, that's another mother-daughter combo that's like identical twins.

GK: Does Ava want to be in the entertainment business? And if you're giving her advice about navigating fame, what is it?

RW: It's an odd situation because I didn't grow up famous. So she's living an experience that I did not have, and so are my sons. We are lucky enough to have friends who grew up in Hollywood and can help give them advice on how to navigate. Ava is so down-to-earth. She wants to do great things in the world. She's studying and learning and trying to find herself. It's a big thing in life to try different things and figure out what is really your path.

GK: Well, right now your path is The Morning Show. I love this show. I see so much realism in how it's done, and I see that some of it is for television. It makes me think morning TV is quite treacherous.

RW: Maybe you know a little bit more than I do, Gayle! I did run into [Good Morning America co-anchor] George Stephanopoulos and he was like, "I'm not sure that this is totally accurate." And I was like, "It's a TV show!" We definitely take liberties. There's a lot of fiction there, but some parts of it feel like they could be anybody's workplace, you know?

GK: There are some liberties, it's true. I get what George was saying. There are some other things that are dead-on. Is there a broadcaster who serves as [your character] Bradley Jackson's main inspiration? I love this girl! She goes from "I'm so happy to be at this job" in Season 1 to telling the boss "Fuck you" in Season 2.

RW: It was great to play this character who was so excited to be invited to the party; then by Season 2 she's entitled, she's a brat, she's advocating for herself but maybe not in the most professional manner. It was fun to play somebody so different from myself. I'm a team player, but that is not Bradley.

Reese Witherspoon
Officine Générale shirt. St. John shorts. Bulgari necklace (top). Almasika necklace and bracelet. Harry Winston watch.
| Credit: Emma Summerton/Dawes+Co

GK: So, she's the opposite of you?

RW: Professionally, yes.

GK: I think it was in Episode 2, she says, "Life just turns out to be a series of disappointments with just enough time in between them for the next one to catch you by surprise." I wrote that down! Did that line resonate with you?

RW: I love that line so much. I said to the writer, "I'm taking my time delivering this line, because it is a doozy." I also have a line in Episode 9 that's really good too about cancel culture and how we don't give people grace to be human and to be genuinely apologetic and remorseful. The writing on this show is so good.

GK: I want to go back to the first question: Is there a broadcaster who serves as your main inspiration for your character?

RW: Well, you!

GK: Uh, let me tell you something: If I said to the boss at CBS, "Fuck you, and I'm going to call in sick for the next month," I swear to you I'd be in Times Square looking for a cab. Taxi! So, who is it really?

RW: I don't know! I think there's people who have understood that they should not be treated poorly and have decided not to go to work because they didn't want to be treated poorly. Look, people know their power; people know their influence. There's an entire new world order, too.

Reese Witherspoon
Thakoon shirt. Versace skirt. Bulgari necklace. Almasika bracelet. Roger Vivier slingbacks.
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GK: A lot of times women don't know their power.

RW: We weren't allowed to exert power. Let's just be clear: Until fairly recently, no one was listening to anything a woman said, and then with the emergence of social media, women have a voice that is undeniable. Women are also hyperaware that they are the buying majority. They hold the purse strings. They also consume much more media than men. When you're talking in terms of my business, it only makes sense to cater to an audience that consumes more than anyone, right? The economics are just so empirical that you can't not listen to women anymore. Enough is enough.

GK: Enough is enough, I get it. I want to talk about Legally Blonde. Twenty years later, we're still talking about Elle Woods. What do you love about that character?

RW: Her optimism and her underdog status are really appealing. What does it mean that she's made a life and a career for herself, but she's still dealing with systemic gender issues? And it's the same with Tracy Flick [from Election]. There's a new Tracy Flick book coming out in June, so it's something that we've been thinking about. Who is she in this moment; what has changed for women in 20 years and what hasn't? We're still not paid the same. We're still fighting for basic human rights. We're still fighting for our constitutional rights.

GK: You also have a lifestyle brand, Draper James. When you're wearing or designing for Draper James, what is it that you want for that person?

RW: When it comes to getting dressed, there's so much noise in the world; I just want to streamline it and make it easy for people. As women, we have other things to concentrate on. We have got to get down to business, Gayle! Additionally, in my 30s, I learned to accept my body for what it is. This is what looks good on it. It will never look good in that thing over there with all the fabric and the bows and the ruffles. It just won't.

GK: I'm still learning this lesson, because I'll see somebody walking down the street looking good in a dress and I'll say, "Whose dress is that?" I'll get the dress, and it looks like crap on me. When am I going to learn that just because it looks good on her it's not going to look good on me?

RW: I fall into that trap all the time. I look at somebody and go, "She looks so good in that." And I realize, "Oh, she's tall. I'm only 5 foot 2; it will not look that good on me."

GK: I'm the reverse. I'll try on something and go,"Oh, she's shorter than I am. Now I look like a fool. I'm trying to be a little too cute."

RW: I'm like a mushroom that grows in somebody's shade.

GK: Never the look I'm going for.

RW: No.

GK: You always look so great on the red carpet, Reese. I know it varies from occasion to occasion, but what's your general approach?

RW: Just classic style. I love designers. What they do is so incredible. Stella McCartney and Phoebe Philo and Tom Ford and Michael Kors — these people are incredibly skilled and gifted at what they do, and I'm sort of trying to showcase their work while also talking about my work.

GK: I'm fascinated too by your book club. How did that come about?

RW: Oprah has paved the way for people to be more literate and to celebrate the joy of reading. I just started posting books on Instagram that I was reading, and then people started making fake book clubs on Facebook that said these are Reese's book picks. And I was like, "Wait, I didn't recommend that book." So I had to make it official, and since then it's just taken off. We don't have an imprint; we're not making money off of selling books. It all goes into literacy programs.

Reese Witherspoon
Greta Constantine jumpsuit. Harry Winston earrings, watch (left), and bracelet.
| Credit: Emma Summerton/Dawes+Co

GK: Yeah, but it's even better when you find a book you love and could make into a movie.

RW: By the way, next year, we have the Where the Crawdads Sing movie coming out; we have the Daisy Jones & the Six TV show. We have another show called From Scratch on Netflix with Zoe Saldana. It's going to be a big year for Hello Sunshine. Which makes me so happy!

GK: You have a lot of things on your plate. Are you looking for more stuff to do?

RW: No! I love what I do, but I don't need any more. I'm so good.

GK: What are you most looking forward to as we start the new year?

RW: More time with people I love. I'm 45. I know who I want to spend time with and who I don't. And that is one of the great things about getting older — it just clears out so much space. I want to be with my mom, my kids, and the people who fill my tank. And everybody else, I wish them well.

Lead Image: Dolce & Gabbana bodysuit and shorts. Bulgari necklace (top). Almasika necklace and bracelet. Ring, her own.

Photography by Emma Summerton/Dawes+Co. Styling by Julia von Boehm. Hair by Adir Abergel/A-Frame. Makeup by Kelsey Deenihan/The Wall Group. Manicure by Yoko Sakakura/A-Frame. Prop styling by Robert Doran/Frank Reps. Production by Viewfinders.

For more stories like this, pick up the December/January issue of InStyle, available on newsstands, on Amazon, and for digital download Nov. 19th.