Reese Witherspoon has always been a step ahead. At just 14, she secured her first major role in “The Man in the Moon” from an open casting call. By her early twenties, she was a celebrated Hollywood star, with successful films like “Election,” “Cruel Intentions,” and later, the iconic “Legally Blonde.” This remarkable drive extended to her personal life: she married actor Ryan Phillippe at 21 and was a mother of two by 27.
However, after winning an Oscar in 2006 for “Walk the Line,” Witherspoon faced professional stagnation and a highly publicized divorce. This challenging period, she revealed, became a catalyst for change. “I had to get truly frustrated and angry in my existing career, to hit a wall, to want to take on a new aspect,” she explained.
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 another Best Actress nomination for her role in “Wild,” a film she helped produce. Her ambitions continued to grow with Hello Sunshine, her next company, which expanded to include a popular book club and produced hit series such as “Big Little Lies,” “Daisy Jones & the Six,” and “The Morning Show,” now in its fourth season. In 2021, Witherspoon sold Hello Sunshine for nearly a billion dollars, yet she remains deeply involved, particularly as the face of its immensely popular 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 gifted teenage actress transform into a formidable entertainment-industry powerhouse, and what self-discoveries did she make along the way? In our extensive conversations, we discussed her early experiences as a young mother in Hollywood, her path out of a professional slump, her transition to a leadership role, and how she navigates the ever-changing landscape of the entertainment world today.
Here you can find the audio recording of the full conversation with Reese Witherspoon.
“The Morning Show” is back, and one of its central themes is that placing women in top leadership positions doesn’t automatically solve all problems. As someone dedicated to working with women, did this resonate with your own experiences? “I’ve never advocated for a matriarchy,” Witherspoon clarified. “I’ve always thought the world needs gender balance. Things swing too far one way or the other. Every time I have the chance to talk about culture inside of Hello Sunshine, I never want to create a monoculture. And I’m also raising two boys. It’s really important that we include men in these conversations. A lot of language and a lot of media from 2017 to 2020 did not include their consciousness or ask them in and help them feel like they belonged in the emergence of the power of women.”
“So I think we have to invite an idea of gender balance. I pushed really hard to get women in seats of power all around me because they weren’t getting the opportunities at all. And I was trying to show it more: women in charge, women as directors, women as screenwriters, women as the author of that best-selling book. So, yeah, it’s interesting that we’re exploring on ‘The Morning Show’ the dynamics of having all these women in charge and how that isn’t always the final answer.”
Image: Reese Witherspoon from a recent season of “The Morning Show.”
Do you believe women exercise power differently? “I do think it’s different. I have a very troubled relationship with the word ‘power.’ It doesn’t feel like something I wanted to achieve or grab at or grasp for. It feels like it could corrupt you, corrode you from the inside in some sort of ‘Lord of the Rings’-esque way. I love leadership, and learning to be a good leader is something I’ve had to do over the past eight years.”
What significant lessons have you learned? “That I’ve got to step up and do it. I had a really pivotal conversation with Shonda Rhimes. We were sitting in a forum with a lot of women — it was about helping people in our business come forward with their stories of sexual harassment and abuse in the workplace. And 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 goes: ‘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 big moment for me. I needed her to tell me that because I would not have seen it.”
I wanted to ask you about a more challenging period. I recall you discussing with Oprah in 2018 your experience of leaving an abusive relationship at a very young age. You mentioned having no self-esteem then and that ending the relationship changed you fundamentally, revealing a strength you didn’t know you possessed. Can you describe that feeling of lacking confidence, as it wasn’t apparent from the outside? “I was very good at being a professional and showing up and doing the right thing, but I wasn’t emotionally mature when I was young. You get into relationships that don’t work for you, and sometimes you don’t even see the dynamics that are happening. When I got out of that, it took me a while to reconstitute myself. My spirit had been diminished because I thought all those awful things that person said about me were true. I had to rewire my brain. But I was really insecure. It took me a long time to be this woman that I am now.”
When you say you had to “reconstitute” yourself, what did that process look like while also being a public figure? “It’s very hard to be a public figure. I have a lot of compassion for people who live public lives and maintain privacy. It’s nearly impossible at this point, with everybody dehumanizing you, taking pictures of you like you’re an animal in the zoo instead of a person with their children. It was really hard. And being a mom and wanting to protect young people is hard too.”
Image: Reese Witherspoon with Ryan Phillippe and their first child, Ava, on the set of “Legally Blonde” in 2000.
You starred in major films like “Election” and “Cruel Intentions” in your early twenties, and of course, married Ryan Phillippe and had children. It was quite uncommon in Hollywood to start a family so young. “You think?” she chuckled. “There are parts of it that are private and personal that I don’t really want to talk about, but I will talk about having kids at a young age. There was so much I didn’t know. And maybe that naïveté was good, because it’s like, ‘Oh, I’ll just do that and have a career.’ And I did have a few people say to me, ‘This is going to be really hard on your career.’ There were roles I couldn’t take. I had to have this immediate balance of family and career, being a mom and being a working actress. That’s why it was also scary when ‘Legally Blonde’ became such a big 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 like, what will I not do?”
Was it challenging to be in a different phase of life than your peers in the industry? “You know what the most ironic part was? I was always being told by people in the industry: ‘Don’t play a mom. It’ll make you seem old.’ And I was like, ‘But, I am a mom.’ There was so much about our business that desexualized you, so you couldn’t be a movie star if you played a mom. And thank goodness, that’s sort of going by the wayside. But that was a big part of when I was in my 20s and 30s: Don’t play a mom. No men will desire you, or nobody will want to go see that movie because nobody wants to see a movie about a mom.”
Were there any individuals you could turn to for guidance on balancing family and career? “As I got a little bit older, Jennifer Aniston was really helpful for me, navigating personal life and tabloid curiosity and also shutting out all the noise. We played sisters on ‘Friends.’ I remember I brought 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 and knocking on the door and going, ‘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 a lot of questions when I went through breakups or a really public divorce, and she was just always very generous with advice and care.”
Image: A candid shot of Reese Witherspoon captured by Philip Montgomery for The New York Times.
What kind of advice did they offer? What were the key takeaways? “Well actually, Jennifer Garner and I, too, are very close. And we would talk a lot about navigating public interest in our kids and how we could protect them from pictures and paparazzi, because they would be 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-producing. I really regret living in L.A. during that time. I know it feels 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 we didn’t get along. 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 it out, away from home, being chased like an animal, and what that kicks up inside your body and what it does for you is very traumatic. I just have incredible compassion for people that went through that time period and were portrayed in a certain way by the media if they went to a nightclub versus they went to the playground. It was a very punishing time for women who were in the spotlight.”
How did you explain these intense situations to your children, and did you observe any lasting effects on them? “My kids had really bad anxiety. And it was all external. You can only shield them from so much, but when they can go to the playgrounds and are on the schoolyard, it feels like the world is chaos and there are no rules. They would yell things at the kids about their dad or me, that were wildly inappropriate.”
At the children themselves? “Yes. These videos exist. And then they would only show the one part where I was screaming back at them, going, ‘Get back in your cars, leave us alone.’ I’m not trying to garner sympathy. It was my life. I just didn’t know that was what would come with 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.’”
Image: Reese Witherspoon speaking during Hello Sunshine’s second annual Shine Away conference in 2024.
You felt this offered a way to control how, when, and to what extent you shared glimpses of your life? “It devalued that market. There was no longer a market to see pictures of my children because people were getting it for free. Also, I immediately saw this opportunity to build community online. How do we take the book club out of your grandma’s living room and into the digital world and create a community that’s far-reaching and global? You know, people come up to 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 execute the bend and snap at 80, you’re in excellent shape. “That’s true. So, people come up to me about ‘Legally Blonde,’ which is cool. And then the other thing is the book club.”
Listen to the full conversation with Reese Witherspoon.
What’s fascinating about your evolution into the businesswoman you are today is that it was preceded by a period where you weren’t creatively fulfilled as an actress. What did you discover about yourself during that time? “Well, I learned that in order to be successful in any business, you have to understand every aspect of it. It forced me to understand the business better, and why they’re not making more movies that I want to be in, or more movies that I would let my daughter watch. It forced me to get analytical. And it started as Pacific Standard, a production company. And that came from two years of going, There’s a missing lane here of developing film that has a woman at the center of it. And then I was like, What if it’s books, too, because I was posting my favorite books on Instagram. And then the two came together, where it was like, Oh, I should option some books to make them into movies. And then it just grew. It also took that shiny part of fame that was so difficult to deal with, and I got to pivot that light onto people who were very deserving. I could stand next to them and promote their books. This is such a great use of fame.”
That brings us back to that initial moment when someone told you, “You are a leader.” “And I had to get really frustrated and angry in my existing career, to hit the wall, to want to take on a new aspect. It’s an entirely different career. It’s two totally different careers. And I jostle between the two of them at all times.”
Can you elaborate on that? “Being a creator and being a person who understands the economics of creating. The part about understanding the shifting economics of the entertainment industry, that’s fun for me now. I like to forecast about it. I write to people who I think have a really good take on our business. And I’ve been inside it since I was 14 years old. I have a very cleareyed opinion of it. I’m not starry-eyed about any of it. You have to be pragmatic when you have a company like mine, because time is your biggest asset. You can’t waste time on things you can’t get made.”
You’re developing a new business venture aimed at Gen Z women. When you forecast trends, what are you observing? “This is part of the great thing about being a young mom: My kids tell me everything that’s going on. 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. Usually people are seeing one movie a year in the theaters with their kids. You’ve got to go where the audience is, not lament the fact that they didn’t show up or have 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. Everybody knows it.”
Image: A portrait of Reese Witherspoon by Philip Montgomery for The New York Times.
Hello Sunshine was acquired by Candle Media in 2021 for nearly a billion dollars. What was that day like for you? “Very emotional. It was a big deal 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 gave up corporate jobs to follow my dreams — all got paid. I also thought, I’ve got to be really careful who this sells to and what the value is, because it’s putting a value on women’s storytelling.”
The CEO of Candle Media recently stated in an interview that while you’ve been a great partner, Hello Sunshine “wasn’t worth what we paid.” How do you respond to that? “I think it’s shortsighted. He and I have talked about it. The world is shifting, and just because one aspect of our company didn’t hit its numbers in a certain 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.”
In that interview, he discussed traditional media’s goal to “retell and extend those stories on social media,” adding that it hadn’t worked out as expected. Could you clarify what he meant by this goal? “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 think after the writers strike and the actors strike, it’s a different time for scripted media. We have live events, we have brand partnerships, we have the book club, and then we have scripted, unscripted. So, there’s so many different components. If one component isn’t working, you don’t just say the whole thing isn’t working. You pivot. And we’re looking at all of that now and going, How can we grow more to where the audience is? But it’s shifting.”
And how do you envision your acting career progressing? “I have to be so passionate at this point to be acting. I have to just love it, love it. Because I really like my life, you know? My real life is really good. So I have to feel like, Oh, the story has to be told. And I do feel like that 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 a lot of parts. I’m not interested in repeating myself.”
What do you believe people often misunderstand about you? “So much. There’s so much people don’t know. I don’t talk a lot about things I’ve been through. I will one day. I’m just not ready yet.”
Is a Reese memoir on the horizon? “No. Maybe I’ll never write the book. My kids know. They know a lot of the things that happen behind the scenes. Some of my really good friends know. But I don’t linger on things either. Every day is a new opportunity to do something meaningful. I don’t hold grudges, and I think that’s what serves me. It pushes me forward. I’m constantly looking to create and not dwell in the old or remember what I was or remember all the wrongs that happened to me. But I do think they would be very, very entertaining, to say the least.”
This interview has been edited and condensed from two conversations. The video was directed by Tre Cassetta.