Reese Witherspoon Tells Tracee Ellis Ross How She Conquered Hollywood

Over the last few years, a funny thing happened to Reese Witherspoon’s IMDb page. The woman who became a teen idol in the ’90s and won an Oscar before she turned 30 has, at least according to the internet, 10 upcoming projects—as a producer. At the age of 45, Witherspoon has bent Hollywood to her will, growing her media company Hello Sunshine—which focuses on stories told about women, by women—into an industry powerhouse that has, among other things, helped reimagine what television can be with shows such as Big Little Lies, The Morning Show, and Little Fires Everywhere. She has also used her influence to embolden Time’s Up, a non-profit, nonpartisan organization that combats gender-based workplace discrimination, alongside some of Hollywood’s most powerful women, one of whom is the actor and producer Tracee Ellis Ross. We’ll let her take it from here. —BEN BARNA

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TRACEE ELLIS ROSS: Reese, you and I got anchored to each other during a really important time, and I got to see firsthand your extraordinary-ness. And before we begin, there are a few things I’d like to say about Reese Witherspoon: You are solution-oriented. You’re one of the hardest workers I’ve ever met in my life. You are not afraid to roll up your sleeves and get in there and be a part of things. You have a business mind like no other human being I have ever met. You are savvy with money and finances. You are advocacy-minded, humanity-based, and fierce—as a friend, a human, a mom, and a wife. You are willing to ask, speak up, and say no, and you understand that “no” is a complete sentence. These are things that all of us can learn from and be inspired by. You are the type of person you want on your team. About a week ago, I had a dream that I was interviewing you. You mom was there and she and I were sitting in a room and crying a lot. I woke up and texted you: “I just had a dream that I was interviewing you and your mom was there and I have no idea what it meant, but I thought I’d say hi.” And now, here we are, having this conversation.

REESE WITHERSPOON: What an intro. I’m blushing. But to be clear, you are definitely one of the hardest-working people I’ve ever met. Every time I talk to you, you’re either writing a book or running a hair care line or on a show. 

TRACEE ELLIS ROSS: Our little group that got connected when we did are all the same kind of woman, and it was really interesting because so often women are expected to be one thing and one thing only, and all of us are so many other things. So here’s my first question for you: How would you define yourself?

WITHERSPOON: Oh, gosh. I’m a mom first. I’m somebody’s daughter. I’ve worked around teams since I was 14 years old, so I definitely think I’m a team leader at this point. I can safely say that. I’m a doer. I don’t like to talk about things for too long, I like to just do them. If they can’t be done, I like to do them and move on. 

ROSS: What is the most important thing to you about who you’ve become? I don’t mean careerwise, but as a person. 

WITHERSPOON: I now know what I’m good at, and I know what I’m not good at. My passions have become more intensified as I’ve gotten older. I truly believe that like-minded people who get together and push toward a greater good can create real change in this world. I only believe that because of the friendships I’ve made with extraordinary women like you over the past, I’d say, four years. Before that, I felt so lonely, and it was really hard for me because a lot of the conversations I was having in rooms in Hollywood, well, I felt like I was the only one having them. When we all started getting together and meeting, I realized that women were having the same conversations across town in a different boardroom or on a different set, and it was enormously comforting to know that I wasn’t pushing a rock up a hill. It’s still a lot of effort, but it felt more effortless with you guys involved. And since then, the support that’s been created by this group of women feels like I have a chorus behind me. 

ROSS: You talk about how real change can be created when there is a sense of community and collective power, and so much of our culture has siloed women off so that we haven’t been able to lean into our collective power, which brings me to this question: What things in our culture that we have been asked to simply accept do you refuse to accept?

WITHERSPOON: The thing that society said for so long, particularly in our business, was that there wasn’t an audience for entertainment that was created by women, with women at the center. And that concept has evolved for me so much since 2011, when I started Hello Sunshine and went around to each studio head and asked, “What are you developing for women?” Other than one studio, they all said, “Nothing.”

ROSS: Nothing?

WITHERSPOON: I’m telling you. It doesn’t even feel like it was that long ago. But I had a studio head say to me, “Reese, we already have a movie with a woman this year. We can’t make another one.” 

ROSS: Oh my god.

WITHERSPOON: And they had no trepidation about admitting that to me. It was just an accepted norm. That was astonishing to me, that they would say it so plainly and that it was something I was supposed to accept. When I started my company, I was like, I’m not going to do it inside of a system that doesn’t philosophically believe that there’s an audience out there that’s bigger than the one that exists. The other thing that really drives me nuts is that women aren’t encouraged to have conversations about financial literacy. And when things drive me crazy long enough, I feel like I’ve got to go do something about it, and it takes me a while to figure out what to do, but I’ll bring it up to literally everybody who crosses my path. You know me as the “How will this make money?” and “Where is the revenue stream?” girl.

ROSS: You’re one of the people who taught me to not only ask that question, but to not be afraid to ask that question, and then to learn what it means when you get the answer. I often talk about how women, particularly Black and brown women, have no historical context for having a stake in what we make. 

WITHERSPOON: The big piece is, how does the artist receive money? We’re in a really unique time where streaming has emerged and social media has become such an important tool for marketing and connecting to audiences. There are so many ways for artists to monetize. But it’s a maze to navigate. I’m always looking for solutions to help build wealth not just for white women, but for Black women, for Latinx women. The reason I talk about it so much is that I’ve walked through rooms where I’ve heard people talk about a piece of material, and about whether or not it mattered in terms of if it made money for a studio. I think about money as an agent of change when used in the correct way, like giving back into communities. I truly believe if women have more money, they invest it in themselves, in their families. And when you look at the stats on what women own, whether it’s home ownership or having any assets, we have got great lengths to go to find equity. Even if we’re making more money, are we getting educated about how to invest? When I first started making money, no one would bring me business opportunities. I was watching my peers, who were men, constantly investing in things like Uber and Google because they hung out with the founders. And I asked other high-profile women, “Were you offered this opportunity?” The answer across the board was no. How you use the money that you get is just as important.

ROSS: How can you tell when a role is one you want or a story is one you have to tell? 

WITHERSPOON: In the past four years, I’ve emphasized positivity and optimism. There’s a tendency to delight in the trauma of women. We see it in the news constantly, and I believe that you can create engaging, deep entertainment without exploiting women. Obviously, at this point in life, comedy is a superpower, so at our company we’re really focusing on comedy. I don’t think things have to be non-impactful just because they’re really entertaining. Especially after this year, we’re looking to our TV shows and our films to show us a hopeful side of humanity.

ROSS: Mary Poppins said it best, Reese. A spoonful of sugar helps the medicine go down.

WITHERSPOON: My husband always says, “When you give a dog medicine, you wrap it in some cheese. It just tastes better if it’s in a little bit of cheese.” That could be the tagline for my company. 

ROSS: By the way, I recently learned that a manager who didn’t end up taking me on after Girlfriends was told by this big management agency that he had to drop his Black female clients because nobody wanted stories about Black women. They didn’t do well, and having Black female clients was not good business. And I was like, “I can’t.” It’s amazing the things that come out of people’s mouths.

WITHERSPOON: That doesn’t surprise me at all. I’ve heard it said that films with Black women or Black comedy in them don’t play overseas. But it is not true. 

ROSS: It’s not true. 

WITHERSPOON: Or that female comedies don’t play overseas. It’s not true. And it’s really interesting how streaming opened up the world of data and the world of media consumption to a global endeavor that could really measure where the audiences were and what they were seeing, and it actually disproved those beliefs. Women are consuming more media than men. There’s empirical data to support that. Those audiences are there and have been there, but have been greatly underserved. It’s also like, “If you never put a women-focused film out, or a film with a Black female lead in it, then how are you ever going to know?” Our salaries are based on those measurements as well, which is radically unfair, right? 

ROSS: That crosses industries. When a system isn’t designed to quantify the data, it doesn’t even see that demographic, so the system just keeps perpetuating itself.

WITHERSPOON: Based on a bunch of lies.

ROSS: Exactly. If they don’t have any imagination to see beyond their own system, the system will never change. And if they continue to use those same numbers to keep justifying business, then the system stays the same. If we keep determining value based on numbers, which is just a diminished version of who all of us are, we lose the whole beauty of the thing which is humanity, a magical thing that can’t be determined by numbers. Do you think television and now streaming is offering different kinds of opportunities than film that feel exciting to you? When I was starting in the industry, TV and film were two wildly different worlds. TV actors didn’t go into film and film actors didn’t go into TV. Has the playing field changed?

WITHERSPOON: Absolutely. I totally heard that coming up in the business. If you were a film actor, you shouldn’t go to TV. Isn’t the most important thing being a part of a story that you believe in? Or having creative autonomy? Film and television are both collaborative mediums. It’s literally about the group of people you assemble because you’re only as good as your creative group. What people don’t know about our business is how much team dynamics go on every day. My most successful results have always been the ones that are the most collaborative. And TV is a bigger commitment than I’ve ever experienced. I just finished season two of The Morning Show and I’ve never worked that long on a project in my whole career. I started when I was 43 and we’re wrapping when I’m 45. 

ROSS: In your career, which role changed you the most? 

WITHERSPOON: Probably Wild. I was so scared to do that, Tracee. I had hypnosis, I was so scared. I was having panic attacks for three weeks before I started. There was the nudity, sexuality, and drug-use aspect, but also being alone on camera with no other actors. I hadn’t ever been alone in scenes for days and days. There were probably 25 days of the shoot where I had no other actor opposite me. It was just me and a camera and a backpack. I was like, “Is this going to be so boring?”

ROSS: It was not. 

WITHERSPOON: And Cheryl Strayed’s book was so beautiful and sacred to me because it spoke to me so deeply about how we as women have to save ourselves. There’s no mother or father coming to save us. There’s no spouse. I thought it was radical that at the end of the film, she ends up with no family, no money, no job, no partner, and she’s happy. 

ROSS: It is radical.

WITHERSPOON: I don’t know if I’ll ever work that hard again, but it changed me on a cellular level. 

ROSS: What are your thoughts on tears, Reese?

WITHERSPOON: On what?

ROSS: Tears. Crying. 

WITHERSPOON: My gosh, I’ve been crying a lot this week. I’ll have memories of my kids when they were little, or I’ll remember my favorite English teacher from high school, and I’ll just burst into tears. As we emerge from this time of hibernation, or whatever it was for people, it really was a time to take stock of who mattered, and I feel overwhelmed with gratitude for how many wonderful people I have in my life. 

ROSS: The reason I ask that question is because there’s so much medicine in our tears. Culturally, as women, we’re not supposed to be angry and crying is considered weak, and I disagree. For people and women who have big lives, filled with responsibilities and dreams and all of it, it’s important to allow those spaces and times when we’ve got to cry, whether it’s out of gratitude, out of discomfort, or out of grief.

WITHERSPOON: Do you cry a lot?

ROSS: I do. But it takes time to get me to tears, and it’s always the most unexpected thing that brings them on. But once they start flowing, I think to myself, “I really needed this.” I’m grateful for them when they come because I think there’s a lot of wisdom in them. Like, your body is not lying. My body is often so much wiser than my mind. I got on my first plane recently and I sat there with my mask on, and the tears were just coming out of my face, simply out of the wildly uncomfortable experience of being around people in a closed space. My body was like, “We’re just going to cry.” What inspires you to keep working hard the way you do? 

WITHERSPOON: I’m passionate about what I do. I love making movies and television shows. I feel so lucky when I stand on set, and years of experience have stacked together to create this time in my life where I can really add, and I can really listen, and I can really be a problem solver, and I can always make something better. That’s such a great feeling. To feel purposeful and useful at work. I also love making people’s lives a tiny bit easier, whether you provide something that’s a reprieve from their daily life, whether it’s a smile you put on their face—it can be as dumb as social media. Honestly, you make me so happy when I see you dancing around on social media. I feel like, “If Tracee can feel that free, I can feel that free.” 

ROSS: Thank you for saying that.

WITHERSPOON: It feels very real. You’re just that kind of person that people want to be around and get to know better. I bet everybody comes up to you and says, “I think you’re my best friend.” Do you get that all the time? 

ROSS: [Laughs] I’m laughing because I do hear that and I love it. So many people don’t get to see the fullness of who they are mirrored back to them, to hear how important they are to someone or how they’ve touched another person or changed something for them. That’s been my experience with social media, but it’s one of the things about this particular career that we have, that you do get to feel that. You walk through an airport and someone tells you they loved what you did. They’re like, “Is it okay that I’m bothering you?” Sometimes you want your privacy, but there’s a beauty in it. Most people in their jobs don’t have someone walk by and say, “I loved the way you gave me my change.” But those people are everywhere. There’s hidden angels everywhere.

WITHERSPOON: True. 

ROSS: How do you like your coffee?

WITHERSPOON: Oat milk, that’s it. I have to have two coffees.

ROSS: Is it vanilla or regular?

WITHERSPOON: I’m not picky. I don’t even know what oat milk is, but suddenly I’m addicted to it. It used to be almond milk but I don’t know what happened. 

ROSS: I have to say that I discovered Oatly strawberry ice cream and I’m sorry I ever did because it has made me a chubby.

WITHERSPOON: Oatly is so delicious and I can’t believe they’re making ice cream.

ROSS: What’s your favorite cocktail?

WITHERSPOON: I like a vodka soda with lime. I drink champagne and ginger ale and whiskey and ginger ale. I drink a lot of ginger ale. 

ROSS: A whiskey and ginger ale? Is that a southern thing? I’ve never heard of such a thing.

WITHERSPOON: I only drink it when I’m in the south, so maybe it is. 

ROSS: What was the last thing that gave you delight? 

WITHERSPOON: Dancing around my kitchen this morning to different Top 40 songs. I’ll do anything to make people laugh, it’s sad. I’m sure my children find it horrifying, but my mother used to do the same thing. 

ROSS: They’ll look back on it fondly and it will probably promote you having a long, fruitful, delicious relationship with your kids the way you do with your mom, because I know how much you love your mom.

WITHERSPOON: That makes me want to cry, the idea of having a long relationship with adult children. I never expected the kind of relationship that I have with them, but it’s so rewarding to be able to have kids that you can process life with a little bit, and they help me understand the complexities of what it means to be a human now. So I’m really, really grateful that these little humans are in my life. Adult humans. I have two adult children now, Tracee. It’s crazy.

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Hair: Lona Vigi using R+CO at A-Frame Agency

Makeup: Kelsey Deenihan at The Wall Group

Set Design: Julien Born at Owl and the Elephant

Digital Technician: Clay Rasmussen

Production: Calum Walsh at North Six

Photography Assistants: Max Dworkin and Kendall Pack

Fashion Assistants: Abi Arcinas, Lucy Gaston, and Hayley Kuniansky

Manicure: Thuy Nguyen using Emilie Heathe at A-Frame Agency