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How Reese Witherspoon Took Charge of Her Career and Changed Hollywood

Tired of dreadful scripts and degrading magazine spreads, Oscar-winning actress, producer, entrepreneur and activist Reese Witherspoon built her own empire.

“You ready for your eyes to roll back in your head?”

The warning comes an hour or so into lunch at L.A.’s members-only San Vicente Bungalows, once Reese Witherspoon has fished her phone from the depths of her designer purse and slid it across the table. There, on her screen, is an illustration that ran four years ago in Time magazine, accompanying a trend piece headlined “Hollywood’s New Domestic Divas.”

The Oscar-winning actress, who at the time had just launched her retail company, Draper James, is in the center, outfitted preposterously with a vacuum, an apron and an evening gown. She’s flanked by Gwyneth Paltrow, holding a strawberry shortcake her Goop devotees wouldn’t dare touch, and Jessica Alba, wielding an iron, despite her Honest company’s focus on diapers and baby wipes. Blake Lively and Lauren Conrad are pictured as well; with a mixing bowl (Lively had a lifestyle site) and cleaning supplies (Conrad’s Little Market sells everything but). They, too, are in formal-wear.

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The passage of four years has not dulled Witherspoon’s outrage. She wondered: Where was George Clooney and his tequila? Or Mark Wahlberg and his burger joints? “What? Men are entrepreneurs but how dare we be anything more than actresses?” she asks, as a pair of attentive waiters clear the remains of her club sandwich. “We, as women, are expected to stay in our lane — that was the inference, and I had sleepless nights over it. I remember calling one of these other women going, ‘What are we doing about this?’ “

Witherspoon, 43, has channeled her fury into a bona fide empire for and about women. Born from frustration — “of people thinking you’re something that you’re not,” she says, “or incapable of something you are” — her 3-year-old company, Hello Sunshine, now has tentacles in television, film, podcasts and publishing, with an online book club poised to one day rival Oprah’s. The 50-person outfit may not bear Witherspoon’s name, but she is the throughline of its every book selection, web series and TV foray: an ultra-successful mom of three who still wakes up every day feeling like she has something to prove.

“She’s one of the most determined people I know,” says Jennifer Aniston, who co-stars with Witherspoon on Apple TV+’s The Morning Show. “She knew what she was up against and she never put that sword down. She had a message and stories to tell and she was just like, ‘Uh-uh, you can’t tell me no and you can’t pat me on the head and say, oh, aren’t you cute.’ ”

At this point, Hollywood wouldn’t dare underestimate her — and of late, it hasn’t. On the TV side alone, Witherspoon has series set up at Netflix, Amazon, Hulu and HBO, and for nearly every one, she’s hands-on from pitch to post. The shows with her onscreen all but guarantee heated bidding wars, along with lavish production budgets wherever they land. In November, Apple launched its entire Apple TV+ content play on Aniston’s and Witherspoon’s shoulders, paying the women a reported $2 million per episode each for their contributions.

Which, to Witherspoon, brings up another bone of contention.

On this early November afternoon, a week after Morning Show‘s debut, she’s hung up on one reviewer’s decision to highlight the size of her paycheck in his critique of the series. “There seemed to be a resentment, as if we weren’t worth it or it was bothersome, and I thought, ‘Why is that bothersome?’ ” she says, declining to identify the outlet or its author (though the Rolling Stone review is easy enough to find).

“I guarantee these companies are real smart, and if they agree to pay us, they’re doing it for a reason. They probably had a lot of lawyers and a lot of business people decide on that number because they knew that they were going to make more than that back.” She pauses, briefly, and then continues: “Does it bother people when Kobe Bryant or LeBron James make their contract?”


If there’s one thing Witherspoon does not lack, it’s experience. Her first turn in front of the camera came at 7, when her parents, a doctor and a labor-and-delivery nurse in Nashville, signed her up for a local commercial. That gig gave way to acting classes, which had led to a starring role in Robert Mulligan’s coming-of-age film The Man in the Moon by 14 — though Witherspoon didn’t instantly drop everything and move west.

Acting, at that point, was just a hobby; school was her passion. “And I was really good at it,” she says. By high school, the straight-A student — who earned the nickname Little Miss Type A, later the name of her first production company — would complain to her teachers when the coursework wasn’t challenging enough.

Witherspoon was accepted to Stanford in 1995, which raised a few eyebrows in her hometown — a patriarchal environment, she explains, where her friends’ fathers would ask, dismissively, “Why would a nice Southern girl want to go to California for school?” Her own parents encouraged her studies, convinced their only daughter needed a solid backup plan. But the acting offers just kept coming, and by Witherspoon’s sophomore year, she’d dropped out to pursue a full-time career in L.A.

She quickly won roles in the 1999 teen noir Cruel Intentions, where she met her first husband, Ryan Phillippe, and in Alexander Payne’s cult classic Election, as uber-confident, uber-grating Tracy Flick. The Hollywood Reporter called her performance in the latter “deliciously driven”; Vanity Fair raved that it was a “career best.” Then, at 23, Witherspoon gave birth to her daughter, Ava, and her whole world changed. “I had to grow up really fast,” she says, “and figure out what woman I wanted to be for my daughter.” She found herself devouring every spiritual book on offer, from the works of Gary Zukav to those of Eckhart Tolle. Her professional choices began to carry more weight, too — and the Chihuahua-toting sorority girl at the center of Legally Blonde didn’t initially fit her vision.

Marc Platt, who’d optioned the book for MGM and pushed for her in the role, recalls Witherspoon’s early hesitation. “She was afraid it was too similar to Clueless, which had recently come out, in terms of the character,” he says, referring to that film’s ditzy, fashion-obsessed Cher, played to perfection by Alicia Silverstone. But Platt told her he was envisioning something closer in tone to Private Benjamin, where Goldie Hawn’s character came into her own in a male-dominated world. “I literally said to her, ‘I want Elle to be a role model,’ ” says Platt. “I wanted my daughters to watch her and think that they can live in a world where they can do anything.”

MGM would require convincing, too. Witherspoon’s indelible performance in Election had put her at risk of being typecast. “They thought I was a shrew,” she says with a healthy smirk. And they weren’t the only ones. At another studio, Witherspoon almost landed several gigs only to be passed over when the decision reached the top office. “My manager finally called and said, ‘You’ve got to go meet with the studio head because he will not approve you. He thinks you really are your character from Election and that you’re repellent.’ And then I was told to dress sexy.”

As the memory floods back, she winces, and then continues: “And you’re 23, you have a baby at home, you need the money and you’re being told that by people who know what they’re doing. It’s funny to think of all the things we were told to do back then because now you’re thinking, ‘Oh God, if somebody told my daughter to do that, she’d be like, I really hope you’re joking.’ “

Witherspoon persevered. She endured multiple rounds of auditions for Legally Blonde, at one point meeting with executives in character (complete with a Southern California accent) to show that she could ace the part. “I remember a room full of men who were asking me questions about being a coed and being in a sorority,” she says, “even though I had dropped out of college four years earlier and I have never been inside a sorority house.”

The ultimate proof was in the box office. Legally Blonde, released in 2001, made $142 million worldwide, and its sequel, released two years later, raked in another $125 million. Suddenly, Witherspoon was America’s Sweetheart, an eight-figure star with the power to cherry-pick projects like Sweet Home Alabama and Vanity Fair. No role, however, was as transformative as her portrayal of June Carter Cash in the 2005 Johnny Cash biopic Walk the Line, which required her to sing. “She knew what a huge challenge that character would be, but she wasn’t going to give up,” recounts Elizabeth Gabler, then head of Fox 2000, which produced the film. “She doesn’t give up.” Critics raved and Witherspoon took home the Academy Award for best actress.

Then … paralysis.

“I was so used to being underestimated that when I was somehow accepted, I didn’t know how to look at material,” she says. “I didn’t know how to make decisions and I didn’t know what I wanted to say.” A string of disappointments followed, forgettable duds like How Do You Know and This Means War, coinciding with a major downdraft in the film business and the demise of her marriage to Phillippe. By 2012, the Oscar winner found herself name-checked in a New Yorker article, along with a handful of other actors who, as the author described them, “were big stars 10 years ago.” It happened to be just what Witherspoon needed.


Reese Witherspoon the producer, much like Reese Witherspoon the entrepreneur, was born out of frustration.

She’d come dangerously close to her breaking point in 2011, when another thankless girlfriend role crossed through her inbox. Witherspoon has alluded to the project in prior interviews and still refuses to name it, going only so far as to shoot down current speculation that it was the 2014 Seth MacFarlane comedy A Million Ways to Die in the West. (“Though I think I auditioned for that,” she says.) The script in question was “dreadful and offensive,” she recalls, an automatic pass. But her reps weren’t as quick to let it go. “You’re the only [major actress] not vying for the part,” they told her.

Witherspoon saw the response as a sign of a much larger problem and requested an audience with each of the town’s studio heads to get a better feel for what was really going on. She asked all seven the same question: What are you developing for a female lead? With one exception, nobody had an answer. “One even said to me, ‘We have a movie with a woman at the center of it, but we’re not going to make two this year,’ ” she says, “without any embarrassment.”

Then came the infamous reference in The New Yorker, the last straw. She’s able to laugh about her “washed-up, has-been” status now, but she certainly couldn’t then. Nevertheless, she forced herself to see it as an opportunity. “Because now I’m underestimated again,” she says. “Sense the theme? Now, I’ve got logs on a fire and I know what to do.”

With a push from her husband, Jim Toth, then a major talent agent at CAA, Witherspoon decided she had the clout, the resources and now the motivation to go at it herself. Rather than try to work within the confines of a studio that wasn’t built for her or her stories, she self-funded her own company, then called Pacific Standard, and began devouring book galleys. Immediately, two stood out: Gillian Flynn’s Gone Girl and Cheryl Strayed’s Wild, both centering on the kind of messy, unconventional female protagonists she wasn’t seeing onscreen. She quickly acquired the rights, promising the authors that, with her, their stories wouldn’t be sanitized.

For a time, there was a question of which film Witherspoon would star in, but Gone Girl director David Fincher answered that for her. The two sat down to discuss the film, and Fincher was brutally honest: “It’s just not you,” he told her, casting the lesser-known Rosamund Pike instead. Gone Girl went on to become a monster hit, grossing $370 million; but whatever residual disappointment there may have been about not being in front of the camera was softened by an Oscar nomination for her leading role in Wild that same year.

Still, it would take Witherspoon a third hit, an adaptation of Liane Moriarty’s Big Little Lies for HBO, to convince the industry of her creative chops. “I was in this position where I was making studios a lot of money, and I had for years and years, and they didn’t take me seriously as a filmmaker. Somehow, they didn’t think that 25 years of experience could add up to some inherent knowledge of what movies work and how to keep them on budget,” she says, before adding: “And you think about the kind of guys who come out of Sundance and get gigantic jobs off of one, like, ‘Oh, I see the potential.’ “

Big Little Lies, a study of female friendship disguised as a soapy crime saga, arrived at an ideal moment and delivered in all the ways she needed it to: ratings, praise and a considerable Emmy haul, including a best limited series win. Witherspoon then willed a second, unplanned season into existence, upping the ante by helping enlist Oscar winner Meryl Streep for the already star-studded ensemble of Nicole Kidman, Laura Dern, Zoë Kravitz and Shailene Woodley. And now, Witherspoon, the Monterey set’s resident organizer of outings and dinner parties, seems keen on a third, assuming they can come up with an idea. “We all love each other,” she says, “and we love those characters.”

On its heels, Witherspoon relaunched her company, rechristened as Hello Sunshine, a “storytelling brand” that would venture far beyond film and TV. She parted ways with former producing partner Bruna Papandrea, and honed her pitch to speak directly to literate women across the country, and not simply on its coasts. She’d host podcasts, newsletters, YouTube videos and live events. And this time, she’d take outside money. Peter Chernin’s Otter Media ponied up. “It was clear to us that this wasn’t just an actress coming in saying, ‘I think I can launch a company,’ ” Chernin says. “She’d already demonstrated through Draper James that she could launch a company, and there was a very sharp, thoughtful business plan in place.”

What came next exceeded even his expectations, as Witherspoon began building out such things as Reese’s Book Club, a natural extension of two loves: reading (she inhales three to four books a week) and social media. Before long, 1.3 million Instagram followers were celebrating the works of female authors like Eve Rodsky and Tembi Locke. Witherspoon has plans to adapt at least a handful of her monthly selections, too, though she insists that isn’t always her goal. She frequently updates her personal feeds as well, a mix of memes, set shots and the occasional peek at her three children (Ava, 20, a college sophomore, Deacon, 16, and, with Toth, Tennessee, 7) for her 20.5 million followers.

At this stage, it would be normal if Witherspoon, bitten by the producing bug, were feeling less drawn to acting; or if, having had a taste for its power, she’d want to direct. But she likens directors to generals in an army, and, despite a reputation for being fierce and exacting, she suggests she isn’t “general material.” Who is? Shonda Rhimes, she offers, and Ava DuVernay, for whom Witherspoon starred in A Wrinkle in Time as an actor-for-hire. (“It was great to leave work and not think about it,” she says.) Instead, Witherspoon, whose personal heroes include other actor-producers like Goldie Hawn and Jane Fonda, says her preferred role is chief creative officer — or, having given it more thought, “chief dreamer.”


Later that afternoon Witherspoon makes her way to The Lot in West Hollywood, where her next potential hit, Little Fires Everywhere, a gripping family drama based on a 2017 Reese’s Book Club selection, recently wrapped production for Hulu.

As her driver idles nearby, she slips into an editing bay, where her fellow producers ply her with music choices to lay over an early, very-1990s montage introducing her character, Elena, a tightly wound mother of four. Witherspoon is decisive and unemotional, quickly dismissing “Beautiful Life” (“too EDM”) and “The Real Thing” (“not Elena”). They try a few more.

“I just don’t know, what is it?” she says following option three, or maybe it was four. “What is that song?”

It’s “Every Heartbeat,” by Amy Grant, her head of TV and film development, Lauren Neustadter, tells her.

“But we didn’t get to the chorus,” says Witherspoon, “so I don’t know that.”

Neustadter hums the chorus.

Witherspoon: “Yeah, but we didn’t get there.”

“Yep,” says Neustadter, suddenly sheepish, “good note.”

If this is a new level of engagement for Witherspoon, who ultimately gives her vote to Annie Lennox’s “Little Bird,” she seems exceedingly comfortable with it. And so, it seems, do those who work alongside her. “We’ve tried to build a culture of being really straightforward,” says Hello Sunshine’s CEO Sarah Harden. “And we can’t be excellent if we don’t name un-excellent things out loud.”

Back at the company’s Los Angeles headquarters, employees are readying some three dozen more projects, including a collection of kids shows and a rom-com slate for WarnerMedia’s HBO Max streaming service. The team still relies heavily on Witherspoon to drum up ideas — “she’s an idea machine,” says Neustadter — and to lure its talent, as she did recently with Zoe Saldana for its Netflix series From Scratch, based on another book club pick. As for those, Witherspoon selects them, too, making personal calls to alert their authors, who often see their books shoot up best-seller lists on Witherspoon’s recommendation.

There will be more Witherspoon star vehicles, too, including a new installment of Legally Blonde. It remains the project that has people — many of them impressionable young women — stopping her daily to gush. Several tell her they went to law school because of Elle Woods. Witherspoon says it’s that response that inspired the revival. Plus, she adds, “I want to discover what age means to that character.” At a recent production meeting with Platt and the film’s original screenwriters, Kirsten Smith and Karen McCullah, Witherspoon doled out pink pencils with fluffy pink poufs as though no time had passed.

With cultural momentum, Witherspoon’s goals keep getting loftier. “I don’t want to just admire problems,” she says, “and I certainly don’t want to leave this business the same way that I found it.” So, in addition to employing scores of women via her Hello Sunshine projects, Witherspoon, a founding and vocal member of the Time’s Up movement, has taken on issues like pay parity, famously cajoling HBO to reshape its entire policy to retroactively ensure the men and women on its shows are paid equally. More recently, she’s been swapping salary data with peers, she says, and advising younger actresses on deal structures to be sure history doesn’t repeat itself.

Friends, like Laura Dern, heap praise on Witherspoon’s heterodox ambition. “It’s been considered a dirty word [to describe] women for far too long,” says her Lies and Wild co-star. Others simply marvel at her capacity. “It’s like watching the hummingbird in my garden,” says Meryl Streep. “Her wings move so fast that she gives the illusion of holding still but she is quicker and brighter and faster than the eye can catch.”

Soon, the conversation comes back to the image of Witherspoon with her gown and vacuum. At the time, she was told to bite her tongue, and accept that that’s simply the world she lives in. But four years later, it still eats at her. “That message — that you shouldn’t dream a little, girls, that you got enough of your pie already — is not OK,” she says. And she’s done staying quiet about it. So, to little girls everywhere, “when people try to tell you to stay in your lane, don’t listen,” says Witherspoon, settling into a smile as she repeats herself: “Do not listen.”



The Watchers
Though her team is loath to define Hello Sunshine as simply a production company, it does have 29 scripted film and TV projects in various stages of development, including a slate of “more inclusive” rom-coms for WarnerMedia’s streaming service and a slew of buzzy book adaptations, from Eleanor Oliphant Is Completely Fine (via MGM) to Daisy Jones & The Six (Amazon), plus another 10 unscripted and animated projects.

The Readers
In addition to her own 2018 Southern lifestyle best-seller, Whiskey in a Teacup, Witherspoon has fostered and fed a digital community of readers, 1.3? million strong. She personally selects and eventizes the club’s monthly picks (all female authors), the past 15 of which made The New York Times’ best-seller list.

The Shoppers
In addition to the merch being peddled on Hello Sunshine’s site (think “Strong Female Lead” pendant necklaces and “Leading Lady” T-shirts), Witherspoon is the face and founder of Draper James, her very Southern retailer that sells dresses, PJs and “Totes Y’all” bags.

And Everybody Else
There’s also a collection of Hello Sunshine podcasts (for, about and hosted by ?women, of course) along with audiobooks, digital series, newsletters and touring events.

This story first appeared in the 2019 Women in Entertainment Power 100 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.