Reese Witherspoon Is Starting a New Chapter

The actress, producer, and media mogul finally takes a (brief) moment for herself.

Reese Witherspoon has described herself as having the energy of “a squirrel who drank coffee.” But just a cursory glance at her laundry list of achievements would seem to indicate that caffeinated-squirrel energy is, well, necessary. “I just look at her and I think, ‘You absolutely exhaust me, just looking at your plate,’ ” Jennifer Aniston, Witherspoon’s costar and coexecutive producer on the Apple TV+ drama The Morning Show, tells me. “She is one of the most highly productive human beings I’ve ever encountered. It’s incredible.”

Among them: HBO’s bingeworthy Big Little Lies, which took home eight Emmys. She runs an influential book club, with 61 picks becoming New York Times bestsellers, plus a Southern-inflected lifestyle brand, Draper James, which includes clothing and home lines. She is also a mother of three.

It’s a sentiment that’s echoed by another Morning Show costar, Julianna Margulies. “I don’t have it in me to do what she does,” says Margulies. “Reese somehow manages to compartmentalize—and she’s good at being in charge.”

In some ways, the breakneck pace and relentless drive seem to mystify even Witherspoon herself. “Gosh, I know. I get really excited about work, so I get tons of nervous energy,” she tells me. “I’m kind of a high-strung person.”

Witherspoon’s close friend and Big Little Lies costar Laura Dern has a kinder, more generous framing for her dizzying output. Dern calls it a “magnificent holy ambition.” Because what propels Witherspoon is a simple mission: centering women’s stories.

Over the past decade, Witherspoon has become something of a crusader for correcting or upending the entrenched Hollywood systems that have excluded and exploited women. “Hello Sunshine was created around the idea that media was largely dominated by male voices and male perspectives, so to be able to create opportunities where women are telling their stories in their own words, you’re just getting a better perspective of the human experience,” she explains. “I think about the limited experience of that expression that my mother had or my grandmother had from artists at that time, because women were so sublimated. It’s just a new time, a new era for women to succeed and excel, and I’m happy to be the rocket fuel they need.”

The beneficence in that project has also proved to be good business: In August 2021, Hello Sunshine was sold to Candle Media, a company run by former top Disney execs Kevin Mayer and Tom Staggs, for a staggering $900 million. That’s a lot of rocket fuel.

When I meet Witherspoon in her hometown of Nashville in early May, there is no trace of caffeinated squirrel. She’s wearing jeans and a floral top, and her hair is cut in a wispy fringe. She seems relaxed, maybe even a little blissed out, from having just seen Taylor Swift on her Eras tour play to a crowd of more than 70,000 at Nashville’s Nissan Stadium. Witherspoon and her 23-year-old daughter, Ava, the eldest of her two children with ex-husband Ryan Phillippe, have caught every single Taylor Swift tour together.

“All I can do is be my most honest, forthright self and be vulnerable…It’s a vulnerable time for me.”

Witherspoon gives me a tour of her office, which is located on the second floor of an immaculately restored and cheerfully decorated Victorian-style building in Nashville’s Germantown neighborhood. (She tells me it’s like the Brooklyn of Nashville.) Witherspoon has been collecting works by women artists, and she proudly points out a framed textile piece by Judy Chicago that hangs behind her desk. In cursive embroidery, it is inscribed with “What if women ruled the world?”

Before meeting Witherspoon, I expected to encounter a mash-up of the traits of the indelible characters she has brought to life: the sunny feminist optimism of Elle Woods, the persistent perkiness of Tracy Flick, maybe even some of the intensity of Big Little Lies’s Madeline Martha Mackenzie.

Perhaps there are some shades of them, particularly Elle Woods. Lauren Neustadter, president of film and TV at Hello Sunshine, tells me that their wrap tradition upon ending big projects is to drink pink champagne in Witherspoon’s trailer. During our interview, Witherspoon drinks a green smoothie that she says she has been drinking every single day for the past 10 years. She will sometimes call the people she encounters “honey” (including me).

In her office, Witherspoon opens a drawer. It’s full of curled-up scrolls of thick paper. It’s a relief to see a corner of her world that doesn’t look Instagram-ready. She unfurls one to reveal a painting of a vase full of flowers. It’s a paint by number, she tells me, and this is her stash of completed works. “I just love them,” she says. “They make me so happy.” She hands me an unopened kit to take home. (She also makes sure I know that the kits are from an Alabama-based women-owned company called Pink Picasso.) “If somebody’s going through something, you can just kind of let go,” she says. “Just paint. Everything kind of fades away.”

Of course, Witherspoon is going through something. In late March, she and her second husband, former CAA power agent Jim Toth, with whom she shares a 10-year-old son, Tennessee, announced their plans to divorce after 11 years of marriage. It would be understandable if Witherspoon had her guard up. Instead, I find her to be grounded, introspective. She is taking time to “get quiet,” she says. She’s painting. She exhorts me to listen to binaural beats, like she does, to fall asleep. “It’s better than any melatonin or sleep aid,” she says. “[It] turns your brain off.”

For all the power and influence Witherspoon now wields, there are ways that fame inhibits control. Her personal life has been tabloid fodder since she was a teenager. She and Phillippe met at her 21st birthday party and costarred in one of the all-time-greatest teen dramas, 1999’s Cruel Intentions, which catapulted them both to the front of the young-Hollywood line. They got married in June of that year, and Ava arrived in September. After the birth of their second child, Deacon, in 2003, Witherspoon talked about being pursued home by five paparazzi. She called the police, and they responded, she said, with a shrug: “Well, aren’t you famous?”

“Worrying about other people’s opinions of you is a waste of your precious time.”

So when news of Witherspoon and Toth’s split broke in March, they were the source, posting a joint statement on Witherspoon’s Instagram account. “It’s interesting what happened to me,” Witherspoon says. “When I was divorced before, the tabloid media got to tell people how I was feeling or how I was processing, and it felt very out of control. To be able to talk to people directly about what’s going on in my life and just share it in the way that I share great professional experiences or personal experiences, it feels much more authentic to be able to say things in my own voice and not let somebody else control what’s happening. Then, of course, there’s speculation, but I can’t control that. All I can do is be my most honest, forthright self and be vulnerable,” she says. “It’s a vulnerable time for me.”

Witherspoon admits that she has slowed down “just a little bit.” “My brain has been going nonstop, and just life changes and running a company,” she says, trailing off. “But that’s okay. I really believe creativity is infinite and you’re just looking for that next bit of inspiration, so if you go through a little slow period, that’s okay.”

Dern, for one, seems relieved. “To see her not on a million calls, not having to read 15 books … to see her taking a moment to not just breathe but also be newly inspired, I’m thrilled for her.”

It feels good, Witherspoon says, putting the news of her divorce out there herself and owning it. “I think about how many other people are going through this experience,” she says. “I don’t feel isolated at all. I feel very connected.”

Witherspoon tells me she usually reads, on average, one book every two days. She credits her paternal grandmother, Dorothea Draper, with sparking her voracious appetite for a good story; she taught Witherspoon to read at the age of four. And Witherspoon says that even as early as high school, she primarily gravitated toward female authors.

In her mid-30s, after two decades of acting and a slew of hits that put her among an elite group of high-earning A-list actresses, Witherspoon started to think more critically about the kinds of stories Hollywood was telling: Who was empowered to tell them? Whose weren’t being told? And why were the scripts she was being sent so lacking? She went around to all of the major studios to ask them what projects they had in the works for women, only to be told they either had none or had already filled their quota of … one women-led picture.

Using her own money, Witherspoon pulled off the hat trick that would establish her as a producing force. She optioned three books to put into production that would offer richer and more nuanced roles for women: Cheryl Strayed’s memoir, Wild; Gillian Flynn’s thriller Gone Girl; and Liane Moriarty’s rich-mom whodunit Big Little Lies.(Nicole Kidman wanted the last one too, so they decided to coproduce it.) In 2014, Wild earned Witherspoon her second Oscar nomination for Best Actress. Gone Girl, released the same year, became a massive hit. Big Little Lies, released in 2017, became a signature HBO series. (Witherspoon produced all three through Pacific Standard, the production company she cofounded with Bruna Papandrea, which was later absorbed by Hello Sunshine.)

Witherspoon proved that she has a knack for knowing not only which books will translate to the screen but also which writers are best suited to adapt them. She approached Nick Hornby, best known for High Fidelity and About a Boy, for Wild. Hornby’s recollection of their meet-cute at an awards-show party is telling of Witherspoon’s deep knowledge of and reverence for writers. Hornby recalls Witherspoon saying, “Nick Hornby, I’m going to give you a hug. You wrote ‘NippleJesus.’ ” Within Hornby’s oeuvre, it was an obscure choice, a short story he’d written for a charity anthology. “It was quite a deep cut, so I was pretty staggered that that was the thing she chose to talk about,” he says.

Hello Sunshine’s creation in 2016 would dovetail with the rise of the #MeToo movement. As women began publicly sharing their stories of abuse and assault within Hollywood, the need for a company like Hello Sunshine felt more urgent than ever. At an awards ceremony the following year, Witherspoon revealed that she had been sexually assaulted by a director when she was 16.

I ask Witherspoon about a film she made earlier in her career, Fear, the 1996 psychosexual thriller in which she starred alongside Mark Wahlberg. Witherspoon was 19 at the time. It’s an otherwise forgettable entry in the Witherspoon canon, but if you were around high school age when Fear came out, you probably saw it. If you did, you probably remember the roller-coaster scene. It’s a fairly tame sex scene in which Witherspoon’s character, Nicole, is digitally stimulated by Wahlberg’s character, David, who is her love interest. But the ingredients—two young actors ascending to peak popularity (Wahlberg, fresh off his 1992 Calvin Klein campaign, was in the process of launching his acting career), a theme-park ride, and the fact that you see a woman orgasm (still a rarity on-screen)—made for a scene that would imprint on countless teenage brains.

“I didn’t have control over it,” Witherspoon tells me matter-of-factly, noting that she requested a stunt double for the below-the-waist scenes. “It wasn’t explicit in the script that that’s what was going to happen, so that was something that I think the director thought of on his own and then asked me on set if I would do it, and I said no. It wasn’t a particularly great experience.”

I tell Witherspoon that I’m sorry that she was put in that position at such a young age, but it’s clear that she isn’t looking for any sympathy and that this story is just one of many that have shaped her. “I’m certainly not traumatized or anything by it, but it was formative,” she says. “It made me understand where my place was in the pecking order of filmmaking. I think it’s another one of those stories that made me want to be an agent for change and someone who maybe can be in a better leadership position to tell stories from a female perspective instead of from the male gaze.”

Witherspoon has more control now; her voice has become one of the most powerful in those rarefied rooms where megadeals are made. The current slate of female-centered and female-led projects recently out or underway at Hello Sunshine is robust: There’s the Fleetwood Mac–inspired Amazon miniseries Daisy Jones & the Six; the Jennifer Garner–led thriller The Last Thing He Told Me, which set a record as Apple’s most-watched limited series; and the third season of The Morning Show, which comes out on Apple TV+ on September 13.

It is Witherspoon’s unique perspective, earned after growing up in the extremely restrictive (if not punishing) version of Hollywood in the ’90s, and willingness to “go to the mat for people,” as she puts it, that have won her the respect—and loyalty—of her peers.

“We have such a sisterhood because we’ve both had to diminish our instincts,” says Dern, who recalls how, for the generation in Hollywood that came before—including Dern’s mother, Diane Ladd, and their family friend Jane Fonda—if a woman wanted to produce, she was infantilized or worse. “They were like, ‘Aww, she’s calling herself a producer.’ There was no respect,” Dern explains. “We’ve both had to fight for our voices and therefore hope to defend others’ voices in workplace environments,” she continues. “She knows how little space there is in a room. She knows that experience. And now that she has that space, she’s lifting up everyone else.”

“Who do I want my daughter to see? I want to be a woman she looks up to.”

“When I was starting my production company, I knew there would be a lot of big learning curves,” says Kerry Washington, another longtime friend and Witherspoon’s coexecutive producer and costar on Little Fires Everywhere, the 2020 Hulu limited series based on Celeste Ng’s novel. “So I was like, ‘Okay, there’s a lot that she’s learned about what to do and what not to do. So I’m going to reach out and say, What advice do you have for me?’ And she confided in me at the time that nobody else had ever called her.”

Witherspoon describes herself as a “glass-half-full-type person.” She’s leaning back these days into the kind of feel-good rom-com roles that were popular in the ’90s and early ’00s, which there seems to be a collective yearning for right now. There’s the perfectly charming and low-stakes Your Place or Mine, released by Netflix this year, in which Witherspoon stars opposite Ashton Kutcher. Now she’s filming (and coproducing) You’re Cordially Invited, a comedy with Will Ferrell for Amazon in which they play feuding wedding planners.

“I think the human capacity to handle as much heartbreak and tragedy that’s happened in the world is really diminished,” Witherspoon says. “We’re just not meant to feel this overwhelmed by sadness and devastation. I think of opportunities to make movies and television shows that are joyful, optimistic, funny—just funny. I think about what I want to see on a Friday night, and while I can appreciate a true-crime show or a podcast, I really need some levity. I think the world is looking for a little brightness.”

This sentiment is somewhat at odds with The Morning Show and her character, the upstart news anchor Bradley Jackson, an unvarnished foil to Aniston’s world-weary network veteran, Alex Levy. The show, rumored to have a budget to rival that of Game of Thrones, is a slick, dark, and tense reflection of the anxieties of the very-recent past. The first season examined the complexities and fallout of #MeToo with a storyline that closely mirrored Matt Lauer’s ouster from the Today show, with Steve Carell playing a longtime host fired amid accusations of inappropriate sexual behavior. The second season added the rise of Covid, the vile disingenuousness of a media conglomerate’s handling of racism, and a surprise romance between Witherspoon’s character and another high-powered anchor played by Margulies.

Witherspoon says that Bradley becomes “a little more manipulative” in season three. “From her relationship with Laura Peterson, Julianna Margulies’s character, to what goes on during Covid, her relationship with her mother and her brother. It’s just a roller coaster.” Season four has already been green-lit.

So how does this square with Witherspoon’s natural inclination toward optimism? Witherspoon says she can relate to the “tenacity that it takes to exist in that environment for as long as [Bradley] has.” Otherwise, Witherspoon acknowledges that Bradley is jaded in ways that she is not.

It wasn’t always this way, though. Witherspoon recounts a period of her life in her late teens and early 20s, pre-Election and Legally Blonde, when she was “very competitive and jealous of other women and not supportive.” “I was really unhappy,” she says. “I was not seeing the abundance of opportunity.”

Witherspoon says she “went hard” for roles in a couple of projects that she ultimately didn’t get. Clueless was one. Baz Luhrmann’s Romeo + Juliet was another. “Oh my God, I wanted to do Romeo + Juliet so badly, so badly,” Witherspoon admits. “Of course, Claire Danes was amazing, but it was devastating to me that I didn’t get it after screen tests and getting really close.”

Witherspoon acknowledges that part of her reaction was simply a result of a system where it felt like “only one girl would make it.” Roles in quirkier films like Pleasantville and Election followed. But when she became pregnant with Ava at 22, she says she knew that “something had to shift” on a more profound level. She asked herself, “Who do I want my daughter to see? I really want to be a woman she looks up to. … I worked on it a lot.”

Like much in Witherspoon’s life, that process involved reading. “Boy, I read a lot of self-help,” she says, name-checking Gary Zukav, Don Miguel Ruiz’s The Four Agreements: A Practical Guide to Personal Freedom, and Marian Wright Edelman’s The Measure of Our Success among the authors and books that got her through.

And then the trajectory of her career began to change. “I got Election and I created Tracy Flick, and I ended up being in Pleasantville, which was amazing. Ava was asking me the other day about where I come up with these characters, like Tracy Flick, Elle Woods, and [Melanie Smooter from] Sweet Home Alabama. I created them all within the span of five, six years in my 20s. …Sometimes I look back and go, ‘How the hell did I do that?’ ”

“I really need some levity. I think the world is looking for a little brightness.”

Witherspoon now exudes a kind of self-confidence and ease with herself—or, to use the parlance of self-help books, self-actualization—that can only come from years of experience and self-work. She is unruffled when I ask about the implosion of Time’s Up, the celeb-studded advocacy group that sprang up in the wake of the Harvey Weinstein harassment and assault allegations. Witherspoon played an instrumental role in fundraising for Time’s Up, but the organization abruptly shut down following revelations that some of its leaders had reportedly advised former New York governor Andrew Cuomo after he was accused of sexual misconduct in 2021. “[It] was an incredible moment in time,” Witherspoon says. “I don’t know if it was ever meant to be forever. I don’t consider myself a career activist. I’m an artist, I’m an entrepreneur, so I don’t really know about the machinations of creating long-standing organizations. I just know that that moment when I was sitting in rooms of women sharing their experiences was really powerful … and we raised a lot of money.” The Time’s Up Legal Defense Fund, which was the recipient of most of the fundraising ($22 million was raised that first year), still exists to help individuals who have experienced sexual harassment with legal fees.

For Witherspoon, the challenges, as well as the successes, have left her with a stronger sense of who she is and what she wants. Aniston notes that “there’s something about getting into your 40s where you just go, ‘I don’t have to fight this anymore. I don’t care.’ Fighting for your narrative? You are your narrative, so just trust in that.”

“I think you start to realize there’s a finite amount of time that you have to accomplish what you want to accomplish in this world and that worrying about other people’s opinions of you is a waste of your precious time,” says Witherspoon. “It’s a liberation in your 40s to feel free of other people’s opinions. I mean, they’re always there. They just don’t matter as much to you, and it’s a great feeling.”