Reese Witherspoon has always been ahead of the curve. She landed her first major role at just 14, starring in “The Man in the Moon” after an open casting call. By her early 20s, she was a Hollywood sensation with hits like “Election” and “Cruel Intentions,” soon followed by “Legally Blonde.” This early success also extended to her personal life: she met her first husband, actor Ryan Phillippe, at 21, and by 27, she was married with two children.
But after her Oscar win in 2006 for “Walk the Line,” Witherspoon faced professional challenges and went through a very public divorce. That period, she explained, compelled her to 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 for and by women. This venture earned her a best-actress nomination for her role in “Wild,” a film she also helped produce. Her ambitions grew further with her next company, Hello Sunshine, where she launched a popular book club and co-produced hit shows like “Big Little Lies,” “Daisy Jones & the Six,” and “The Morning Show,” which just began its fourth season on Apple TV+. 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 widely loved book club. “I watch culture,” she noted. “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 precocious teenage actress transform into an entertainment-industry powerhouse, and what has she discovered about herself along the way? In our extensive conversations, we discussed her early days in Hollywood as a young mother, her path out of a career slump, becoming a boss, and how she navigates the current volatile landscape of Hollywood.
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“The Morning Show” is back, and a central theme is that simply having women in top positions doesn’t automatically solve all problems. As someone who champions working with women, does this resonate with your own experiences? Well, I’ve never advocated for a matriarchy. I’ve always believed the world needs gender balance. Things tend to swing too far in one direction or the other. Every time I discuss company culture at Hello Sunshine, I strive to avoid creating a monoculture. And I’m also 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 consider their perspectives or invite them to feel included in the rise of women’s power.
So, I think we need to foster an idea of gender balance. I worked diligently to place women in positions of power around me because they weren’t getting those opportunities at all. And I aimed to highlight it more: women in charge, women as directors, women as screenwriters, women as the authors of best-selling books. So, yes, it’s intriguing that on “The Morning Show,” we’re exploring the dynamics of having all these women in charge and how that isn’t always the ultimate solution.
Do you believe women exercise power differently? I do think it’s different. I have a very complex relationship with the word “power.” It doesn’t feel like something I ever wanted to achieve, grasp, or hold onto. It feels like it could corrupt you, corrode you from the inside, in a “Lord of the Rings”-esque way. I value leadership, and learning to be a good leader is something I’ve actively pursued over the past eight years.
What significant lessons have you learned about leadership? That I simply have to step up and do it. I had a truly pivotal conversation with Shonda Rhimes. We were sitting at 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 remember saying: “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 monumental moment for me. I needed her to tell me that because I wouldn’t have realized it myself.
I wanted to ask you about a more challenging time in your life. 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 transformed you at a cellular level — simply realizing that you were someone who could leave such a situation. I was wondering if you could describe what that lack of confidence felt like, because from an outside perspective, it wasn’t obvious. I was very adept at being professional, showing up, and doing what was expected, but I wasn’t emotionally mature when I was young. You enter relationships that aren’t healthy for you, and sometimes you don’t even perceive the dynamics at play. When I finally exited that situation, it took me a while to reconstitute myself. My spirit had been diminished because I believed all those awful things that person said about me were true. I had to rewire my brain. But I was genuinely insecure. It took me a long time to become the woman I am today.
When you say you had to “reconstitute” yourself, what does that process look like when you’re also a public figure? It’s incredibly difficult to be a public figure. I have immense compassion for those 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 instead of a person with their children. It was very tough. And being a mom while wanting to protect young people is also challenging.
Yes, I wanted to address this: You starred in major films in your early 20s — “Election,” “Cruel Intentions” — and, of course, got married and had children. Ryan Phillippe was your husband then. Great pronunciation.
I had to look it up! [Laughs.] It was quite unusual, I think, in Hollywood to have kids in your early 20s. You think? [Laughs.] Parts of it 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 perhaps 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 very hard on your career.” There were roles I couldn’t take. I had to immediately balance family and career, being a mom and a working actress. That’s why it was even scarier 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 more daunting, because I wasn’t picking and choosing what I would strive for. It was more about, what will I not do?
Was it difficult to be in a different phase of life than your peers? 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 in our business that desexualized you, so you couldn’t be a movie star if you played a mom. And thankfully, that’s slowly disappearing. But that was a significant part of my 20s and 30s: Don’t play a mom. No men will desire you, or no one will want to see that movie because no one wants to see a movie about a mom.
Were there people you could turn to for support with that balance you were trying to achieve? As I got a little older, Jennifer Aniston was incredibly helpful to me, navigating personal life and tabloid curiosity, and also tuning 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.” And 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.
What kind of advice was that? What were the lessons? Well, Jennifer Garner and I are also very close. And we would often talk about managing public interest in our kids 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 my divorce, and chasing us like it was a police chase, down the freeways. It was terrifying. It was truly hard on my kids. Anxiety-inducing. I genuinely 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. And there’s a little boy and a little girl there.
I watched them chase Britney Spears. She had two little children and I had two little 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, away from home, being hunted like an animal, and what that triggers inside your body and what it does to you is very traumatic. I just have incredible compassion for people who endured that period and were depicted in a certain way by the media, whether they went to a nightclub or a playground. It was a very punishing time for women in the spotlight.
How did you explain that to your kids? And did you observe the effects on them? My kids experienced really bad anxiety. And it was all external. You can only protect them from so much, but when they’re at playgrounds or on the schoolyard, it feels like the world is chaotic and without rules. People would yell wildly inappropriate things at the kids about their dad or me.
At the children? Yes. These videos exist. And then they would only show the one part where I was screaming back at them, saying, “Get back in your cars, leave us alone.” I’m not seeking sympathy. It was my life. I just didn’t realize that was part of wanting to be an actor. That’s why when social media emerged, Jennifer Garner and I got on the phone and said, “Oh, my God, we can decide when people have pictures of our kids? Sign me up.”
You felt like this was a way for you to control how much and when you would open the door to the public? It devalued that market. There was no longer a market to see pictures of my children because people were getting them for free. Also, I immediately recognized this opportunity to build an online community. How do we move the book club out of your grandma’s living room and into the digital world, creating a far-reaching and global community? You know, people approach me about two things: “Legally Blonde,” of course. They like to say, “What, like it’s hard?” and “Can you do the bend and snap?”
They actually ask you to do the bend and snap? Yeah. And sometimes I do the bend and snap! If you see me do the bend and snap, you’re very lucky 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.
If you can still do the bend and snap at 80, you’re in a good place. That’s true. So, people approach me about “Legally Blonde,” which is cool. And then the other thing is the book club.
What’s particularly fascinating about your transformation into the businesswoman you are today is that, before this, you experienced a professionally fallow period where you weren’t creatively pursuing your desired projects. What did you learn about yourself during that time? Well, I learned that to be successful in any business, you have to understand every aspect of it. It compelled me to understand the business better, and why they weren’t making more movies that I wanted to be in, or more movies that I would let my daughter watch. It forced me to be analytical. And it started as Pacific Standard, a production company. That came from two years of realizing, there’s a missing lane here for developing films centered around women. And then I thought, What if it includes books, too, because I was posting my favorite books on Instagram. And then the two merged, where it was like, Oh, I should option some books to adapt them into movies. And then it just grew. It also allowed me to take that challenging, shiny part of fame and redirect that spotlight onto deserving individuals. I could stand alongside them and promote their books. This is such a wonderful use of fame.
This brings me back to something you said earlier, that initial moment when someone told you: You are a leader. And I had to become really frustrated and angry in my existing career, to hit a wall, to want to embrace a new dimension. It’s an entirely different career. They are two completely distinct careers. And I constantly juggle between the two of them.
Could you elaborate on that? Being a creator and being someone who understands the economics of creating. The part about understanding the shifting economics of the entertainment industry, that’s enjoyable for me now. I like to forecast about it. I correspond with people who I believe have a really insightful perspective on our business. And I’ve been involved in it since I was 14 years old. I have a very clear-eyed view of 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 be realized.
You’re initiating a business project aimed at Gen Z women. When you’re forecasting, what trends are you observing? I’d love to know. This is one of the great advantages 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. People usually see one movie a year in theaters with their children. 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 shifting. The way we make movies is going to change radically in the next two to three years.
Because of AI? Mmm-hmm. Everyone knows it.
Your company was acquired by Candle Media in 2021 for almost a billion dollars. What was that day like? Very emotional. It was a big moment for me because I had truly held firm during those negotiations and waited for the best valuation, because so many women had equity in the company, and it was crucial to me that these women—who gave up corporate jobs to pursue my dreams—all received fair compensation. I also thought, I have to be very careful who this sells to and what the value is, because it’s placing a value on women’s storytelling.
The CEO of Candle Media recently gave an interview where he said you’ve been a great partner, but he also remarked that Hello Sunshine “wasn’t worth what we paid.” How does that comment affect you? 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 lacks value. 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.
In that interview, he discussed how the goal with traditional media is now to “retell and extend those stories on social media,” and he added that this goal hadn’t worked out as well as expected. I didn’t quite understand what he meant. Yeah, we can ask him. You want to call him?
But do you understand what he means? Can you explain what the current goal is? 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, we have brand partnerships, we have the book club, and then we have scripted, unscripted content. So, there are so many different components. If one component isn’t performing, you don’t simply declare the whole thing isn’t working. You pivot. And we’re evaluating all of that now, asking, How can we further grow where the audience is? But it is constantly shifting.
And where do you see your acting career heading? I have to be incredibly passionate at this point to be acting. I have to just love it, truly love it. Because I genuinely enjoy my life, you know? My real life is really good. So I have to feel like, Oh, this story absolutely has to be told. And I do feel that way about some of our projects. But it’s definitely a different feeling 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 many roles. I’m not interested in repeating myself.
What do you think people don’t understand about you? So much. There’s so much people don’t know. I don’t talk extensively about things I’ve experienced. I will one day. I’m just not ready yet.
Is a Reese memoir in the works? 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 presents a new opportunity 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 on the past or remember who I was or all the wrongs that happened to me. But I do think those stories would be very, very entertaining, to say the least.
Director of photography (video): Tre Cassetta