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Interviewing Reese Witherspoon is a nerve-racking business. Back in 2019 she was launching her Apple TV+ drama The Morning Show at a West Hollywood hotel filled with bustling black-clad Apple PRs and jet-lagged international journalists.

I was finally shown in to the silent oasis of a room where she waited with co-star Jennifer Aniston. The pair were sitting on separate wide, soft sofas, the still centre of this PR tornado. Witherspoon was poised, precise and projected a ferocious intelligence. When she turned her piercing blue eyes on me, I got the sense that she was analysing my questions in the way a scientist examines a creature under a microscope. 

It’s journalistic etiquette to start with a soft lob, flattering sweet nothings to warm up the subject. Witherspoon was unimpressed, offering short, to-the-point replies. Even when we reached #MeToo, ostensibly the topic of the show, she was guarded. Had the pair ever encountered a Harvey Weinstein-style character on their way up? 

Last August, Forbes magazine named Reese Witherspoon (pictured) the world’s richest actress, having delivered everything she set out to do

‘Sure,’ Witherspoon gave a tight-lipped nod. ‘I definitely did.’ Then Aniston chipped in: ‘I didn’t to a level of aggression that some of them have experienced. I think Me Too kicked it really intensely in the back end.’ Although I wanted to pursue Witherspoon on her experiences, with interview time running out, we had to move on. So I asked about the founding of her production company, Pacific Standard, in 2012 (which later become Hello Sunshine) and the inspirational speech she made at Glamour magazine’s Women of the Year Awards back in 2015. She turned sharply and held me in her gaze for a second. I’d hit the point that interested her the most. ‘I think Jen and I are uniquely positioned as women who have had success within one iteration of Hollywood and are now experiencing an entire new landscape,’ she said. ‘The emergence of streaming has allowed women to have an ascendency and to be heard and valued in a way that we never had been before.’ 

Her confidence in this was being backed by Apple’s cash – the company paid the two stars a reported $2 million each per episode of The Morning Show – but Witherspoon’s looming payday was so much bigger. In August last year, she sold a majority share of Hello Sunshine to Candle Media – founded by former Disney executives Kevin Mayer and Tom Staggs – for a cool $900 million. 

In 2019 Reese Witherspoon launched her Apple TV+ drama The Morning Show, which she stared in with Jennifer Aniston

In 2019 Reese Witherspoon launched her Apple TV+ drama The Morning Show, which she stared in with Jennifer Aniston

Reese Witherspoon (L), winner of the Oscar for best actress, and her mother Betty pose together at the Governor's Ball following the 78th annual Academy Awards in Hollywood, 2006

Reese Witherspoon (L), winner of the Oscar for best actress, and her mother Betty pose together at the Governor’s Ball following the 78th annual Academy Awards in Hollywood, 2006

In that Women of the Year acceptance speech, she laid out the reality of life as an actress in 21st-century Hollywood. As she got older, she had noticed the scripts were drying up. ‘When I got into the film business, I was doing dramas, and casting directors didn’t know if I could be funny,’ she said. ‘So I did a comedy, Legally Blonde, and then they didn’t think I was serious. So I did dramas, and they didn’t think I was funny. And I got older, and they didn’t think I could still be viable.’ 

s Reese Witherspoon speaks onstage at the 2015 Glamour Women of the Year Awards in 2015

s Reese Witherspoon speaks onstage at the 2015 Glamour Women of the Year Awards in 2015

She arranged meetings with the heads of the big studios and asked how many movies with a female lead were in development. None, she was told. And the studio heads didn’t seem bothered. She told her audience she dreaded reading scripts that were written only by men because she would always get to a scene where the girl turns to the guy and says, ‘What do we do now?’ 

With social media we can figure out what audiences want to see 

‘Do you know any woman in any crisis situation who has absolutely no idea what to do?’ she asked. The crowd laughed. ‘But I couldn’t turn to some man and say, “What do we do now?” This is my life. I’ve made movies since I was 14 years old. It was time to turn to myself and say, “OK, Reese, what are we going to do now?” The answer was clear. My mother, a strong, smart Southern woman, said to me, “If you want something done, honey, do it yourself.”’ 

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So she did. Witherspoon founded her own production company and started optioning books written by women about women. Within two years she had produced two movies: Gone Girl and Wild. Between them, they made over half a billion dollars and won three Oscar nominations. Last August, Forbes magazine named Witherspoon the world’s richest actress, having delivered everything she set out to do. She had carved out a role as a Hollywood player in an industry that really didn’t want anything to do with her. 

REESE IN NUMBERS  

40.1 million 

Followers on social media across Twitter, TikTok and Instagram

 $900 million 

What her production company Hello Sunshine was valued at in 2021 

The number of awards she received for Walk the Line: an Oscar, Bafta, Critics Choice Award and SAG Award 

$634.2 million 

Box office takings for her biggest hit, Sing 

12 million 

The average audience per episode for season 2 of Big Little Lies

73 

The books picked by Reese’s Book Club since June 2017 

$430 million 

Her net worth, according to Forbes, making her the world’s richest actress 

38 

The number of films she’s starred in 

$20 million 

Reportedly what she was paid for ten episodes of The Morning Show 

‘She’s the optimum operator in Hollywood,’ explains Ian Nathan, the former editor of Empire who co-presents Discovering Film on Sky Arts. ‘She’s reached an extraordinary level of producer power, alongside the likes of Ryan Murphy [Glee, Eat Pray Love and Dahmer]. But she still acts and, if anything, her acting is getting better and better. She takes whitebread-roles with a sense of reality and adds a little commentary. In the history of Hollywood many actresses have tried to break through like that, but very few have succeeded.’ 

Succeeding is what Witherspoon does. In her Nashville high school, she earned the nickname ‘Little Miss Type A’ after complaining to her teachers when the coursework wasn’t challenging enough. Her parents, a doctor and a nurse, signed her up for a local TV commercial when she was seven, which led to acting classes and a role, aged 14, in Robert Mulligan’s The Man in the Moon. She still saw acting as a hobby and in 1995 won a place to study English Literature at the prestigious Stanford University. 

Hollywood, however, wouldn’t let her go. In 1996 she won roles in two movies – Fear, alongside Mark Wahlberg, and Freeway with Kiefer Sutherland – so dropped out and was cast in the teen noir Cruel Intentions, where she met her first husband, Ryan Phillippe. They married in 1999 and their daughter Ava was born that same year. A son, Deacon, followed in 2003. By this time her role as Elle Woods in Legally Blonde had made her a bona fide star and in 2005 Walk the Line earned her the best actress Oscar. 

Her romcom period that followed – which saw her in flops like How Do You Know, Water for Elephants and This Means War, and which she now describes as ‘floundering career-wise’ – ground to a halt in 2010. By 2012, she found herself in an article in The New Yorker, along with a handful of other actors who ‘were big stars ten years ago’. 

That was the kick she needed to talk to studio heads and take control of her career. She started a clothing line, Draper James, to give herself an income that would allow her to be more selective in her script choices. Despite her success with Gone Girl and Wild the year before, in 2015, a few months before her Glamour speech, Time belittled her in an article headlined ‘Hollywood’s New Domestic Divas’. The magazine mocked up images of Witherspoon, Gwyneth Paltrow, Blake Lively and Jessica Alba holding cakes, irons or the washing up. Reese’s image was given a vacuum cleaner. 

‘We decided we’re going to be entrepreneurial, we were going to do something, take a swing, invest our own money, our own time, our reputation and try and do something that George Clooney has done, Robert De Niro has done – and we were getting lampooned for it,’ she told Kristen Bell on her podcast in 2021. ‘That message to little girls is if you’ve had success in one area, you can’t have success in another.’ 

Time magazine picked the wrong Type A actress to mock. In 2016 she started work as star and producer on Big Little Lies for HBO – based on the bestselling book by Liane Moriarty and co-starring Nicole Kidman and Laura Dern – which aired in 2017. 

‘It had a huge impact,’ says Nathan. ‘She did something modern and made it about women and mothers and their lives. It encapsulated Witherspoon’s brand as one of modern, mature womanhood. You have to give her respect in the way she cultivated that.’ 

Reese with dog Pepper in 2019, at home,  reading one of the novels she adapted for TV

Reese with dog Pepper in 2019, at home,  reading one of the novels she adapted for TV

That year she also launched her own online book club, spotlighting women authors, and plucking certain titles to make into movies and TV shows. The book club also includes newsletters, YouTube videos and live events. Hollywood stopped underestimating her, fast. On the TV side alone, Witherspoon has series on Netflix, Amazon, Hulu and HBO, and for nearly all of them, she’s hands-on, from the pitch to post-production. She’ll stand in the editing booth choosing songs for the soundtrack or walk into a studio chief’s office with an ironic Elle Woods fluffy pen. Everything she touches produces heated bidding wars, big production budgets and high salaries. The launch I attended for The Morning Show was such a big deal because Apple was launching its entire Apple TV+ content play on her shoulders. 

But Candle Media paid close to $1 billion for more than just the success of a few decent scripts. ‘Witherspoon’s smarts is in understanding social media and data to help bypass gatekeepers,’ says one strategist at a Hollywood streaming company. ‘She learnt it through her clothing line Draper James which uses data to decide on which products would sell. She has a knack for knowing her audience, but she can also use the social data and book sales to show how popular storytellers already are. Women make 85 per cent of purchase decisions, three-quarters of financial decisions and they comprise half of the box office. She brings them in like no one else.’ 

With her Big Little Lies co-stars Laura Dern, Nicole Kidman, Zoë Kravitz and Shailene Woodley at the Golden Globe Awards, 2018

With her Big Little Lies co-stars Laura Dern, Nicole Kidman, Zoë Kravitz and Shailene Woodley at the Golden Globe Awards, 2018

Kevin Mayer, who was briefly TikTok’s CEO, agrees. He chose Witherspoon’s company because she knows how to use her book club and podcast to build a social-media fanbase who buy what she recommends. The future media company, he says, combines ‘content, commerce and community’. 

Witherspoon agreed. ‘Years ago, I was making movies in a vacuum,’ she told news channel CNBC. ‘I never really knew who was seeing them, what their feelings were. Now, I have this one-on-one relationship with people all over social media. We can really figure out exactly what audiences want to see.’ 

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And that’s been the secret to her success – realising that the easiest way to build her company was reaching around those studio heads who saw no problem with a men-only slate and talking directly to the women who felt the same as her. She quickly understood Instagram, has 28.5 million followers and shifted 2.4 million of those over to her book club, where she plugs new books, her forthcoming shows based on books and has sponsors such as Lavazza. 

Reese with her husband talent agent Jim Toth at the 2017 Vanity Fair Oscar Party hosted by Graydon Carter

Reese with her husband talent agent Jim Toth at the 2017 Vanity Fair Oscar Party hosted by Graydon Carter

‘The special sauce is Reese herself,’ says a source close to the book club decision-making process. ‘From the outside people sometimes assume that she’s not always directly involved, but she’s the final pair of eyes and makes the choice for every one of the book-club picks. With her years of experience in film and TV, she has an instinct for which titles could also work on the screen. What it comes down to is decades experiencing the ups and downs of showbusiness, a love of the written word that borders on obsession, an ability to read at a furious pace and great taste.’ 

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Witherspoon also has a knack for picking up novels that will go on to be bestsellers – Eleanor Oliphant is Completely Fine, Daisy Jones & the Six and Where the Crawdads Sing, for instance, were all part of her book-club-to-screen producer’s plan. 

‘Reese has taken things to another level,’ according to media analyst Tom Harrington at Enders Analysis. ‘Maybe Oprah, Jane Fonda and Gwyneth Paltrow have done something similar, but she’s taken it further – she’s doing business deals, producing shows with purpose, expanding internationally and getting almost a billion in investment purely on the strength of her name. She owes this to her entrepreneurial nature, but also her very clean image – everyone forgets the “Do you know who I am?” thing.’ 

He’s referencing the actor’s low point in 2013 – after the all-male studio chiefs meetings but before Gone Girl – when her second husband, talent agent Jim Toth, with whom she has a ten-year-old son Tennessee, was pulled over for driving under the influence. Witherspoon asked the officer ‘Do you know my name? You’re about to find out who I am… you’re about to be on national news.’

 It’s a rare celebrity who can yell at police on camera, have it leaked to the internet and have everyone pretty much forget it happened. Reese Witherspoon, however, is a rare celebrity. This year alone she has been producer on movies Where the Crawdads Sing and Something from Tiffany’s, the documentary Fair Play, the TV series Surface, Daisy Jones & The Six, From Scratch, Tiny Trailblazers and Tiny Beautiful Things. She’s acting in a third series of The Morning Show, has been cast in Disney’s Tinker Bell, is working with Will Ferrell on a movie due to start shooting next year, and Hello Sunshine has opened its first UK division. Oh yes, and she’s about to start pre-production on Legally Blonde 3, reprising the role that made her name. 

When she was first offered the part of the bubblegum-pink-loving Elle Woods more than 20 years ago, Witherspoon almost turned it down, worried it would be too close to Alicia Silverstone’s airhead in Clueless. She wanted something she could show her daughter that would make her think that anything was possible. The viewing public agreed. The first version ended on the steps of the courthouse after Woods won her case and kissed her man Emmett, played by Luke Wilson. 

Test audiences didn’t care for it, the film’s writer Karen McCullah recalls. ‘The kiss didn’t feel right because it wasn’t about their relationship. Audiences were saying, “We want to see what happens – we want to see her succeed.” So that’s why we rewrote her graduation speech.’ 

Witherspoon has ended up living the life she wanted her daughter to believe in, she explained when I interviewed her. ‘When little girls came up to me ten years ago and said, “I wanna be in Hollywood” I wouldn’t have said “Go try and be a director, go try and be a writer”.’ She gave a tight smile. ‘I would have said, “That’s not really an avenue to explore.” Now I can say that with confidence. Write your own stories, direct your own material, go to film school. It actually might happen.’ 

She leaned forward a little, as if making sure I understood. ‘This is a whole new ball game.’

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