Reese Witherspoon has always been a step ahead. She landed her first major role at just 14 years old in “The Man in the Moon” after an open casting call. By her early twenties, she was already a prominent Hollywood figure with hits like “Election,” “Cruel Intentions,” and later, the iconic “Legally Blonde.” This same driven energy extended to her personal life: she met her first husband, actor Ryan Phillippe, at 21 and was married with two children by 27.
However, after winning an Oscar in 2006 for “Walk the Line,” Witherspoon faced a professional dry spell and a highly publicized divorce. This challenging period, she revealed, became a catalyst for change. “I had to get really frustrated and angry in my existing career, to hit the wall, to want to take on a new aspect.”
This new direction led her behind the camera. She co-founded Pacific Standard, a production company dedicated to telling stories by and for women. This venture led to an Oscar nomination for her role in “Wild,” a film she also helped produce. Her ambitions continued to grow with her next company, Hello Sunshine. She launched a wildly popular book club and co-produced successful shows such as “Big Little Lies,” “Daisy Jones & the Six,” and “The Morning Show,” which recently premiered its fourth season. In 2021, Witherspoon sold Hello Sunshine for nearly a billion dollars, though she remains actively involved in its daily operations and is the public face of its celebrated book club. “I watch culture,” she explained. “I’ll watch TikTok almost like a scientist would watch it. I want to see where the ball is going in my business.”
So, how did a gifted teenage actress transform into an entertainment powerhouse, and what has she discovered about herself along the way? In our extensive conversations, we delved into her early years in Hollywood as a young mother, her path out of a career slump, her transition into leadership, and how she navigates today’s turbulent Hollywood environment.
You can listen to the full conversation with Reese Witherspoon on Apple Podcasts, Spotify, YouTube, Amazon Music, or iHeartRadio, or stream it through the New York Times Audio app.
Question: “The Morning Show” is back, and one of its themes explores how putting women at the top doesn’t automatically solve all problems. As someone who prides herself on working with women, did that particular theme resonate with your own experiences?
Answer: Well, I’ve never advocated for a matriarchy. I’ve always believed the world needs gender balance; things can swing too far in one direction. Whenever I discuss culture within Hello Sunshine, I always aim to avoid creating a monoculture. And as a mother raising two boys, it’s crucial that we include men in these conversations. Much of the discourse and media from 2017 to 2020 didn’t always consider their perspectives or invite them to feel a sense of belonging amidst the rising power of women.
Therefore, I think we need to foster an idea of gender balance. I fought hard to place women in positions of power around me because they simply weren’t getting opportunities. I wanted to actively demonstrate it: women as leaders, as directors, as screenwriters, as the authors of best-selling books. So, yes, it’s fascinating that on “The Morning Show,” we’re exploring the complexities of having all these women in charge and how that isn’t always the definitive solution.
Question: Do you believe women exercise power differently?
Answer: I do think it’s different. I have a very complicated relationship with the word “power.” It doesn’t feel like something I ever wanted to attain or grasp for. It feels like it could corrupt you, corrode you from within, in a sort of “Lord of the Rings”-esque way. I do, however, love leadership, and learning to be an effective leader is something I’ve had to cultivate over the past eight years.
Question: What have you learned?
Answer: That I have to step up and take action. I had a really pivotal conversation with Shonda Rhimes once. We were in a forum with many women, discussing how to help people in our industry come forward with their stories of sexual harassment and abuse in the workplace. I said, “If we could just get people to show up at this one event, that would be great. Somebody’s going to have to get them there.” She patted my leg and said, “You’re going to do it. They’re going to listen to you. And when you tell them to show up on Thursday at 5 p.m. at your office, they’re going to come, because you’re the leader but you don’t know it.” That was a huge moment for me. I needed her to tell me that because I wouldn’t have seen it myself.
Question: I wanted to ask you about a more challenging period. I saw you discussing with Oprah in 2018 about leaving an abusive relationship when you were very young. You mentioned having no self-esteem back then and that leaving the relationship changed you on a cellular level – simply realizing you were someone who could leave such a situation. I’m curious if you could elaborate on what that lack of confidence felt like, because from the outside, it wasn’t apparent.
Answer: I was very adept at being professional, showing up, and doing what was expected, but I lacked emotional maturity when I was young. You enter relationships that aren’t healthy for you, and sometimes you don’t even recognize the dysfunctional dynamics at play. After I left that situation, it took me a while to put myself back together. My spirit had been diminished because I believed all the terrible things that person said about me were true. I had to rewire my brain. I was truly insecure. It took me a long time to become the woman I am today.
Question: When you say you had to “reconstitute” yourself, what did that process look like when you’re also a public figure?
Answer: It’s incredibly difficult to be a public figure. I have immense compassion for people who live public lives and strive to maintain privacy. It’s almost impossible now, with everyone dehumanizing you, taking pictures of you as if you’re an animal in a zoo rather than a person with your children. It was incredibly hard. And being a mom while wanting to protect young people is also challenging.
Question: Yes, I wanted to address this: You starred in big films in your early 20s—“Election,” “Cruel Intentions”—and, of course, got married and had children. Ryan Phillippe was your husband then.
Answer: Great pronunciation.
Question: I had to look it up! [Laughs.] It was unusual, I think, for someone in Hollywood to have kids in their early 20s.
Answer: You think? [Laughs.] There are aspects of it that are private and personal that I don’t really want to discuss, but I will talk about having kids at a young age. There was so much I didn’t know. And maybe that naïveté was a good thing, because it was like, “Oh, I’ll just do that and have a career.” And I did have a few people tell me, “This is going to be really hard on your career.” There were roles I couldn’t take. I immediately had to balance family and career, being a mom and a working actress. That’s why it was also frightening when “Legally Blonde” became such a massive hit. I wasn’t going to beg for parts; parts were coming to me. And that almost made it scarier, because I wasn’t picking and choosing what I would reach and strive for. It was more about, what will I not do?
Question: Was it difficult to be at a different stage in life than your peers?
Answer: You know what was most ironic? I was constantly told by people in the industry, “Don’t play a mom. It’ll make you seem old.” And I thought, “But, I am a mom.” There was so much about our business that desexualized you, implying you couldn’t be a movie star if you played a mother. Thankfully, that’s slowly changing. But that was a significant part of my twenties and thirties: Don’t play a mom. No man will desire you, or no one will want to see that movie because nobody wants to see a movie about a mom.
Question: Were there people you could turn to for help with the balance you were trying to achieve?
Answer: As I got a little older, Jennifer Aniston was incredibly helpful for me in navigating my personal life and tabloid curiosity, and also in shutting out all the noise. We played sisters on “Friends.” I remember bringing my baby, Ava. Ava was only three months old when I was on “Friends” in 1999. And I remember Courteney [Cox] and Jen coming to my dressing room, knocking on the door, and saying, “We heard you have a baby!” I was like, “I do. I have a baby!” They were like, “Can we see it? Oh, my God, this is so cool.” I just remember them being so kind about it. That kindness opened a door for me to ask Jennifer many questions when I went through breakups or a very public divorce, and she was always very generous with advice and care.
Question: What kind of advice was that? What were the lessons?
Answer: Well, Jennifer Garner and I are also very close. We would talk a lot about navigating public interest in our children and how we could shield them from pictures and paparazzi, because they were everywhere. All over the schools and all over the cars. I remember at church once in L.A., a guy jumping on the hood of the car and on each side, three people pushing against the window, banging on the door when my kids were little after I got a divorce, and chasing us like it was a police chase, down the freeways. It was terrifying. It was really hard on my kids. Anxiety-inducing. I truly regret living in L.A. during that time. I know it seems like they’re just taking pictures, but it would be like 25 people on the side of the soccer field photographing me and Ryan to see if we got along or didn’t get along. And there’s a little boy and a little girl there.
I watched them chase Britney Spears. She had two small children, and I had two small children, and I felt like it was this really unfair portrayal of her as a “bad girl,” and that I was a “good girl.” She was a young mother trying to figure things out, far from home, being hunted like an animal. And what that stirs up inside your body, what it does to you, is deeply traumatic. I have incredible compassion for people who lived through that era and were depicted in a certain way by the media, whether they went to a nightclub versus a playground. It was a very punishing time for women in the spotlight.
Question: How did you explain that to your kids? And did you observe any effects on them?
Answer: My kids developed really bad anxiety. And it was entirely external. You can only protect them from so much, but when they’re on playgrounds and in schoolyards, it feels like the world is chaotic and without rules. People would yell things at the kids about their dad or me that were wildly inappropriate.
Question: At the children?
Answer: Yes. These videos exist. And then they would only show the part where I was screaming back at them, saying, “Get back in your cars, leave us alone.” I’m not trying to gain sympathy. It was my reality. I just didn’t realize that was what would accompany wanting to be an actor. That’s why when social media emerged, Jennifer Garner and I got on the phone and we were like, “Oh, my God, we can decide when people have pictures of our kids? Sign me up.”
Question: You felt this offered a way for you to control how much, when, and in what manner you shared glimpses of your children?
Answer: It devalued that market. There was no longer a demand for pictures of my children because people were getting them for free. Also, I immediately recognized the opportunity to build a community online. How do we take the book club out of your grandma’s living room and bring it into the digital world, creating a far-reaching, global community? You know, people approach me about two things: “Legally Blonde,” of course. They love to say, “What, like it’s hard?” and “Can you do the bend and snap?”
Question: They actually ask you to do the bend and snap?
Answer: Yeah. And sometimes I do the bend and snap! If you see me do the bend and snap, you’re very fortunate because I think I’ve only done it a handful of times. Am I going to be an 85-year-old lady sitting on a porch, doing the bend and snap on Instagram? God, I hope not.
Question: If you can still do the bend and snap at 80, you’re in a good place.
Answer: That’s true. So, people come up to me about “Legally Blonde,” which is cool. And then the other thing is the book club.
Question: What’s particularly fascinating about your evolution into the businesswoman you are today is that before this, you experienced a period of professional stagnation, where you weren’t creatively pursuing what you desired. What did you discover about yourself during that time?
Answer: Well, I learned that to be successful in any business, you must understand every aspect of it. It compelled me to better grasp the industry, and why they weren’t making more movies I wanted to be in, or more movies I’d let my daughter watch. It pushed me to become analytical. And it began as Pacific Standard, a production company. That came from two years of realizing, there’s a missing space here for developing films with women at their core. Then I thought, what if it extends to books too, because I was sharing my favorite books on Instagram. And then the two merged, where it was like, Oh, I should option some books to adapt into movies. And it just expanded from there. It also allowed me to redirect the intense glare of fame, which was so challenging, onto deserving individuals. I could stand beside them and promote their books. This is a wonderful way to utilize fame.
Question: That brings me back to something you mentioned earlier—that initial moment when someone told you, ‘You are a leader.’
Answer: And I had to get truly frustrated and angry in my existing career, to hit a wall, to want to embrace a new dimension. It’s an entirely different career. It’s two completely separate careers. And I constantly juggle between the two of them.
Question: Explain that to me.
Answer: Being a creator and also someone who understands the economics of creation. The aspect of understanding the shifting economics of the entertainment industry—that’s enjoyable for me now. I like to forecast trends. I correspond with people I believe have a really sharp insight into our business. And I’ve been immersed in it since I was 14 years old. I have a very clear-eyed perspective on it. I’m not starry-eyed about any of it. You have to be pragmatic when you run a company like mine, because time is your most valuable asset. You can’t waste time on projects that can’t realistically be made.
Question: You’re launching a business project aimed at Gen Z women. When you’re forecasting, what trends are you observing? I’m very curious to know.
Answer: This is part of the great advantage of being a young mom: my kids tell me everything that’s happening. So that helps. I noticed my kids weren’t going to the movies. I had teenage kids. I went to the movies every Friday and Saturday night. Kids don’t go to the movies anymore. Usually, people are seeing one movie a year in theaters with their kids. You have to go where the audience is, not lament the fact that they didn’t show up or suffer from what I call “old-school-itis,” which is like, Well, in my day. Well, it just doesn’t work that way! Attention spans are changing. The way we make movies is going to transform radically in the next two to three years.
Question: Because of A.I.?
Answer: Mmm-hmm. Everybody knows it.
Question: You were acquired by Candle Media in 2021 for almost a billion dollars. What was that day like?
Answer: Very emotional. It was a significant moment for me because I had really held out during those negotiations and waited for the best valuation, because so many women had equity in the company, and it was really important to me that these women—who left corporate jobs to pursue my dreams—all got paid. I also thought, I have to be extremely careful about who this sells to and what the value is, because it’s placing a value on women’s storytelling.
Question: The C.E.O. of Candle Media recently gave an interview where he said you’ve been a great partner, but also that Hello Sunshine “wasn’t worth what we paid.” How do you feel about that statement?
Answer: I think it’s shortsighted. He and I have discussed it. The world is changing, and just because one aspect of our company didn’t hit its numbers in a particular year, that doesn’t mean it’s not valuable. And I think: Gosh, don’t try to bury something that’s a seed! It’s going to grow and grow and grow, because it’s a wonderful brand and it stands for something.
Question: In that interview, he discussed how the current goal with traditional media is to “retell and extend those stories on social media,” adding that this goal hadn’t worked out as well as he expected. I didn’t understand what he meant.
Answer: Yeah, we can ask him. You want to call him?
Question: But do you understand what he means? Can you explain the current goal?
Answer: I can’t explain what he was trying to say, because I don’t know. I don’t live inside his head. But I do believe that after the writers’ strike and the actors’ strike, it’s a different era for scripted media. We have live events, brand partnerships, the book club, and then we have scripted and unscripted content. So, there are so many different components. If one component isn’t performing, you don’t just say the whole thing isn’t working. You pivot. And we’re evaluating all of that now, asking, How can we expand further to reach audiences where they are? But things are definitely shifting.
Question: And where do you see your acting career heading?
Answer: At this point, I have to be incredibly passionate to take on an acting role. I have to just love it, truly love it. Because I genuinely like my life, you know? My real life is really good. So I have to feel like, Oh, the story absolutely has to be told. And I do feel that way about some of our projects. But it’s definitely a different sentiment about acting. I’ve also been doing it since I was 14, so I’ve done a lot, I’ve said a lot, I’ve played a lot of parts. I’m simply not interested in repeating myself.
Question: What do you think people don’t understand about you?
Answer: So much. There’s so much people don’t know. I don’t talk much about things I’ve experienced. I will one day. I’m just not ready yet.
Question: Is a Reese memoir on the horizon?
Answer: No. Maybe I’ll never write the book. My kids know. They know many of the things that happen behind the scenes. Some of my really good friends know. But I don’t dwell on things either. Every day is a new chance to do something meaningful. I don’t hold grudges, and I believe that serves me well. It propels me forward. I’m constantly looking to create and not linger in the past or recall who I was or all the wrongs that occurred. But I do think they would be very, very entertaining, to say the least.
This interview has been edited and condensed from two conversations.
Director of photography (video): Tre Cassetta