Reese Witherspoon has always been a trailblazer. She landed her first major acting gig, the lead in “The Man in the Moon,” at just 14 years old after an open audition. By her early twenties, she had already cemented her status as a Hollywood A-lister, starring in acclaimed films like “Election” and “Cruel Intentions,” quickly followed by the iconic “Legally Blonde.” This early success extended to her personal life: she met her first husband, actor Ryan Phillippe, at 21, and by 27, she was married with two children.
However, following her 2006 Oscar win for “Walk the Line,” Witherspoon faced a challenging period marked by a scarcity of desirable roles and a highly publicized divorce. This difficult phase, she revealed, became a catalyst for change. “I had to get incredibly frustrated and angry with my career,” she explained, “to really hit a wall and realize I needed to embrace a new direction.”
This fresh path led her to filmmaking. She co-founded Pacific Standard, a production company dedicated to telling stories by and for women, which earned her a Best Actress nomination for her role in the film she helped produce, “Wild.” Her vision expanded further with her next venture, Hello Sunshine. Under this new banner, she launched a successful book club and co-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 actively involved in its daily operations and continues to be the beloved face of its popular book club. “I constantly observe culture,” she shared, “I study platforms like TikTok with a scientific curiosity, always looking to anticipate future trends in my industry.”
So, how did this once precocious teenage actress transform into a formidable entertainment industry mogul? And what profound insights has she gained along the way? In our extensive discussions, we delved into her early experiences in Hollywood as a young mother, her journey out of a career lull, her evolution into a powerful executive, and how she currently navigates the ever-changing landscape of the entertainment world.
Listen to the full conversation with Reese Witherspoon. This actor and producer landed her first significant role at just 14 years old. Over three decades later, she stands as a true powerhouse in the entertainment industry.
Question: “The Morning Show” has returned, exploring the idea that simply placing women in top positions doesn’t automatically solve all problems. As someone dedicated to collaborating with women, did this theme resonate with your personal experiences?
Reese Witherspoon: “I’ve never advocated for a matriarchy,” she stated. “My belief has always been that the world thrives on gender balance. Extremes in either direction aren’t beneficial. Whenever I discuss our culture at Hello Sunshine, I’m conscious of avoiding a monoculture. Furthermore, as a mother of two boys, it’s vital to include men in these conversations. Much of the discourse and media from 2017 to 2020 often overlooked their perspectives, failing to invite them into the dialogue surrounding the rising power of women.”
“Therefore, I believe we must actively promote the concept of gender balance. I worked diligently to ensure women held positions of power around me, recognizing they were severely lacking opportunities. My goal was to visibly demonstrate women leading – as directors, screenwriters, and authors of best-selling books. It’s certainly compelling to delve into the dynamics on ‘The Morning Show,’ examining how an all-female leadership isn’t always the ultimate solution.”
Visual: A captivating image of Reese Witherspoon during the fourth season of “The Morning Show.”
Question: Do you believe women wield power differently?
Reese Witherspoon: “I do think it’s distinct,” she responded. “I have a complicated relationship with the term ‘power.’ It doesn’t feel like something I ever aimed to acquire or cling to. It carries a sense that it could corrupt you, eroding you from within, much like something out of ‘Lord of the Rings.’ I genuinely value leadership, and developing into an effective leader has been a journey over the last eight years.”
Question: What key lessons have you learned during this time?
Reese Witherspoon: “I’ve learned that I simply have to step up and take action,” she shared. “I had a truly transformative conversation with Shonda Rhimes. We were at a forum with many 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 amazing. Someone will have to rally them.’ Shonda gently patted my leg and said: ‘You’re going to do it. They’ll 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 are the leader, even if you don’t realize it yet.’ That was a profoundly significant moment for me. I needed her to vocalize it because I wouldn’t have recognized it myself.”
Question: I’d like to touch on a more challenging period. I recall you discussing with Oprah the experience of leaving an abusive relationship at a very young age. You mentioned having no self-esteem then, and how breaking free transformed you at a fundamental level – simply realizing you could exit such a situation. Could you describe what that lack of confidence felt like, as it wasn’t apparent from the outside?
Reese Witherspoon: “I excelled at being professional, showing up, and doing what was expected, but I lacked emotional maturity in my youth,” she reflected. “You find yourself in relationships that aren’t healthy, and sometimes you’re blind to the underlying dynamics. After I left, it took considerable time to rebuild myself. My spirit had been eroded because I believed all the terrible things that person had said about me were true. I had to literally rewire my brain. I was profoundly insecure, and it’s taken me a long journey to become the woman I am today.”
Question: When you refer to “reconstituting” yourself, what did that process entail while living such a public life?
Reese Witherspoon: “Being a public figure is incredibly challenging,” she noted. “I have immense empathy for anyone living in the public eye who strives to maintain privacy. It’s almost impossible now, with people dehumanizing you, photographing you as if you’re an animal in a zoo rather than a person with their children. It was extraordinarily difficult. And as a mother, wanting to shield your children from all of that, is equally tough.”
Visual: A candid moment of Witherspoon with Ryan Phillippe and their daughter, Ava, on the set of “Legally Blonde” in 2000.
Question: Moving on to your early twenties: you starred in major films like “Election” and “Cruel Intentions,” and then married Ryan Phillippe and had children.
Reese Witherspoon: “Excellent pronunciation,” she quipped.
Question: I had to double-check the pronunciation! (Laughs.) It was quite uncommon in Hollywood to start a family in your early twenties.
Reese Witherspoon: “You think?” she responded with a laugh. “Some aspects are deeply private and personal, which I prefer not to discuss. However, I’m happy to talk about having kids at a young age. There was so much I didn’t yet learn. Perhaps that naïveté was a blessing, as it allowed me to think, ‘Oh, I’ll just manage a career and a family.’ A few people did warn me: ‘This will significantly impact your career.’ Indeed, there were roles I couldn’t accept. I was immediately faced with balancing family and a demanding acting career. That’s why the massive success of ‘Legally Blonde’ felt even more daunting. Suddenly, I wasn’t auditioning; roles were being offered to me. This made it almost scarier, as my challenge shifted from striving for specific roles to deciding what I simply would not do.”
Question: Did you find it challenging to be at a different life stage compared to your peers?
Reese Witherspoon: “The most ironic thing,” she recalled, “was constantly being told by industry insiders: ‘Don’t play a mom. It will make you appear old.’ And my response was: ‘But I am a mom!’ Our industry, at that time, heavily desexualized you; you couldn’t be a movie star if you played a maternal role. Thankfully, that archaic notion is gradually disappearing. But throughout my twenties and thirties, a significant message was: ‘Never play a mom. No man will find you desirable, or no one will want to watch a movie about a mother.’”
Question: Did you have mentors or peers you could turn to for support in balancing your life?
Reese Witherspoon: “As I matured, Jennifer Aniston became an invaluable resource,” she shared. “She helped me navigate my personal life, handle tabloid intrusion, and effectively block out external noise. We played sisters on ‘Friends,’ and I distinctly remember bringing my three-month-old daughter, Ava, to the set in 1999. Courteney [Cox] and Jen came knocking on my dressing room door, exclaiming, ‘We heard you have a baby!’ I confirmed, ‘I do! I have a baby!’ They were so excited, asking, ‘Can we see it? Oh, my God, this is so cool!’ Their kindness truly stood out. That moment opened the door for me to frequently seek Jennifer’s advice during my own breakups or highly publicized divorce, and she was consistently generous with her guidance and support.”
Visual: A photograph taken by Philip Montgomery for The New York Times.
Question: What kind of advice did she offer? What were the key takeaways?
Reese Witherspoon: “Jennifer Garner and I are also very close,” she added. “We often discussed how to manage the public’s intense interest in our children and how to shield them from relentless photographers and paparazzi, who seemed to be everywhere – at schools, around our cars. I vividly recall an incident at church in L.A. where a man jumped onto the car hood, and three others pressed against the windows, banging on the doors, all while my young children were inside, shortly after my divorce. They chased us down the freeways like a police pursuit; it was absolutely terrifying and deeply distressing for my kids, causing significant anxiety. I genuinely regret living in L.A. during that period. While it might seem like ‘just taking pictures,’ having perhaps 25 people on the sidelines of a soccer field photographing Ryan and me to analyze our interactions, with a young boy and girl right there, was simply too much.”
“I witnessed firsthand the relentless pursuit of Britney Spears. She, like me, was a young mother with two small children. I felt a profound injustice in how she was unfairly painted as a ‘bad girl,’ while I was often labeled a ‘good girl.’ Britney was a young mom, far from her support system, trying to navigate life while being hounded like an animal. That kind of pressure is incredibly traumatic, affecting you on a deep, physical level. I have immense compassion for anyone who endured that era, when the media would harshly judge women in the spotlight based on whether they were seen at a nightclub or a playground. It was a brutal time for famous women.”
Question: How did you explain these situations to your children, and what impact did you observe on them?
Reese Witherspoon: “My children developed severe anxiety, and it was entirely due to external factors,” she responded. “You can only protect them so much, but once they’re at playgrounds or schoolyards, it feels like the world is chaos and there are no rules. People would shout wildly inappropriate things at them about their father or me, that were wildly inappropriate.”
Question: They directed these shouts at your children?
Reese Witherspoon: “Yes. These videos exist. And then they would only show the one part where I was screaming back, going, ‘Get back in your cars, leave us alone!’ I’m not seeking sympathy; this was simply my reality. I truly never anticipated this would be part of the package when I chose to become an actor. That’s why, when social media started to emerge, Jennifer Garner and I immediately connected. We were like: ‘Oh my God, we can finally control when pictures of our kids are shared? Sign us up!’”
Visual: Reese Witherspoon delivers a powerful speech at Hello Sunshine’s second annual Shine Away conference in 2024.
Question: So, you felt this new platform allowed you to control the narrative — how much, when, and in what manner you chose to share?
Reese Witherspoon: “It completely devalued the market,” she explained. “There was no longer a demand for paparazzi photos of my children because people could get them for free elsewhere. Beyond that, I immediately recognized the immense opportunity to foster an online community. How could we transition the traditional book club from a cozy living room setting into the digital sphere, creating a far-reaching, global community? Interestingly, people approach me about two main things: ‘Legally Blonde,’ of course. They love to quote, ‘What, like it’s hard?’ and ask, ‘Can you do the bend and snap?’”
Question: They actually ask you to perform “the bend and snap”?
Reese Witherspoon: “Yes, and sometimes I actually do it!” she admitted. “If you ever witness me doing the bend and snap, consider yourself very fortunate, as I’ve probably only done it a handful of times. Will I be an 85-year-old woman on a porch, doing the bend and snap for Instagram? I certainly hope not!”
Question: If you can still perform “the bend and snap” at 80, you’ll be in excellent shape!
Reese Witherspoon: “That’s true,” she agreed. “So, people frequently approach me about ‘Legally Blonde,’ which is cool. And the other big topic is my book club.”
Question: It’s fascinating how you transitioned into the businesswoman you are today, especially given that it followed a professionally dormant period where you weren’t finding fulfilling creative work. What did you discover about yourself during that time?
Reese Witherspoon: “I realized that to truly succeed in any industry, you need a comprehensive understanding of every facet of it,” she explained. “That period compelled me to better grasp the business, and why studios weren’t producing more films I wanted to star in, or more films I’d feel comfortable letting my daughter watch. It forced me to become analytical. This led to the founding of Pacific Standard, a production company, born from two years of recognizing a gap in the market for films centered around women. Then I thought, ‘What about books?’ because I was already sharing my favorite reads on Instagram. The two ideas converged, and I began optioning books to adapt into movies. From there, it simply blossomed. It also allowed me to redirect the often difficult ‘shiny’ aspect of fame. I could shine that spotlight onto deserving individuals, standing alongside them to promote their books. This feels like a truly meaningful application of my public platform.”
Question: That brings us back to your earlier remark about the pivotal moment when someone told you, “You are a leader.”
Reese Witherspoon: “And I genuinely had to reach a point of deep frustration and anger in my established acting career, to truly hit a wall, before I was ready to embrace a new path,” she elaborated. “It’s a completely distinct profession. These are two entirely different careers, and I’m constantly balancing both.”
Question: Could you elaborate on that?
Reese Witherspoon: “It’s about being a creative force while also understanding the economic realities of production,” she clarified. “Navigating the evolving economics of the entertainment industry is genuinely enjoyable for me now. I love to anticipate trends. I regularly connect with people I believe have astute insights into our field. Having been in this business since I was 14, I possess a very clear-eyed perspective; there’s no starry-eyed idealism for me. When you run a company like mine, you absolutely must be pragmatic, as time is your most valuable asset. You simply cannot afford to waste time on projects that won’t come to fruition.”
Question: You’re launching a business venture targeting Gen Z women. When you’re “forecasting” trends, what are your observations? I’m eager to hear.
Reese Witherspoon: “One of the great advantages of being a young mom is that my children keep me completely informed about what’s happening,” she revealed. “That’s a huge help. I noticed my kids weren’t attending movies. When I was a teenager, I went to the cinema every Friday and Saturday night. Today’s youth simply don’t go to movies. Most families are lucky if they see one film a year in theaters with their children. You absolutely have to meet your audience where they are, rather than complaining that they didn’t show up or succumbing to what I call ‘old-school-itis,’ thinking, ‘Well, back in my day…’ That approach simply doesn’t work anymore! Attention spans are dramatically shifting. The entire process of filmmaking is poised for radical transformation within the next two to three years.”
Question: Because of AI?
Reese Witherspoon: “Mmm-hmm. Everyone knows it’s coming.”
Visual: Another photograph taken by Philip Montgomery for The New York Times.
Question: In 2021, you were acquired by Candle Media for nearly a billion dollars. What was that experience like?
Reese Witherspoon: “It was incredibly emotional,” she reflected. “It was a monumental moment for me because I deliberately stood firm during those negotiations, insisting on the best possible valuation. It was paramount that the many women who had equity in the company – women who left established corporate careers to pursue my vision – were all fairly compensated. Additionally, I recognized the immense responsibility of carefully choosing the buyer and ensuring the valuation reflected the true worth of women’s storytelling.”
Question: 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 react to that?
Reese Witherspoon: “I believe that’s a shortsighted perspective,” she stated. “He and I have discussed it. The world is constantly evolving, and just because one part of our company didn’t meet its targets in a particular year doesn’t diminish its inherent value. My thought is: Don’t try to bury a seed! It has the potential to grow and flourish because it’s an exceptional brand that stands for meaningful values.”
Question: In that same interview, he discussed the current goal for traditional media being to “retell and extend stories on social media,” noting that this hasn’t yielded expected results. I found that comment difficult to understand.
Reese Witherspoon: “Perhaps we should ask him,” she suggested. “Do you want to give him a call?”
Question: But do you have an understanding of his meaning? Could you explain the current objectives?
Reese Witherspoon: “I can’t interpret what he was trying to convey, as I’m not privy to his thoughts,” she replied. “However, I do believe that in the aftermath of the writers’ and actors’ strikes, the landscape for scripted media has fundamentally changed. We now engage with live events, brand collaborations, our book club, alongside both scripted and unscripted content. There are so many diverse elements. If one component isn’t performing as expected, you don’t simply dismiss the entire endeavor as a failure. You pivot. And that’s precisely what we’re doing now – examining all avenues to determine how we can expand and reach audiences wherever they are. It’s an incredibly dynamic environment.”
Question: Looking ahead, what’s your vision for your acting career?
Reese Witherspoon: “At this stage, my motivation for acting has to stem from intense passion,” she emphasized. “I genuinely have to love, truly love, a project. You know, my personal life is incredibly fulfilling. So, for me to act, I have to feel an undeniable pull – that ‘this story absolutely needs to be told.’ I do feel that way about some of the projects we develop. But my perspective on acting has certainly evolved. Having been in this profession since I was 14, I’ve done, said, and played a vast array of roles. I have no interest in repeating myself.”
Question: What do you believe people often misunderstand about you?
Reese Witherspoon: “So much,” she mused. “There’s a great deal people don’t know. I don’t often discuss many of my past experiences. I will, one day. I’m just not ready to share them yet.”
Question: Is a Reese Witherspoon memoir on the horizon?
Reese Witherspoon: “No,” she replied. “Perhaps I’ll never write that book. My children are aware; they know many of the behind-the-scenes stories. Some of my closest friends also know. But I don’t tend to dwell on the past. Every day presents a fresh opportunity to do something significant. I don’t hold grudges, and I believe that mindset genuinely benefits me. It propels me forward. I’m always focused on creating, not lingering on past identities or rehashing the injustices I’ve faced. Although, I do think those stories would be incredibly entertaining, to say the least.”
This interview has been carefully edited and condensed from two separate conversations.
Video Director of Photography: Tre Cassetta