Six complex women — also including Nicole Kidman, Jessica Lange, Elisabeth Moss and Chrissy Metz — debate the power and pain of strong females (onscreen and off-) amid a culture of discrimination in the industry and beyond: “I don’t think we’ve ever seen this much misogyny.”

When Oprah Winfrey decided to adapt The Immortal Life of Henrietta Lacks for HBO, she had two actresses in mind to play the role of Lacks’ daughter Deborah. But HBO Films president Len Amato wasn’t interested in her casting ideas: He wanted the media tycoon to be involved onscreen as well as off-. And after some heavy arm-twisting and a little time to get comfortable with the idea, Winfrey, 63, agreed — in part because the role allowed her to showcase, as she puts it, “a whole range of craziness.” It’s the opportunity to explore those layers of character and emotion that has drawn her and five other stars — Nicole Kidman, 49; Reese Witherspoon, 41; Elisabeth Moss, 34; Jessica Lange, 68; and This Is Us breakout Chrissy Metz, 36 — to work on television, as they revealed during The Hollywood Reporter’s annual Drama Actress Roundtable discussion on a Hollywood soundstage in May. “We have the opportunity to show the entire spectrum of human emotion that women have,” says Witherspoon, who, like Kidman, is a producer and star of HBO’s Big Little Lies. “We aren’t just the wives and the girlfriends. We are actually living, breathing people who have insecurities.” During the course of an hour, the six spoke candidly about the unexpected rewards and residue that come with inhabiting complicated women.

You have tackled ageism, sexism, misogyny, depression, domestic abuse, adultery and rape. When was the last time you were genuinely nervous to tackle a storyline?

OPRAH WINFREY (The Immortal Life of Henrietta Lacks, HBO) I was genuinely nervous to take on the role of Deborah Lacks because look at this table. I come as the least experienced person at this table. I come as a person who has great respect for the craft of acting — and for years interviewing actresses and being inspired by actresses, but not developing the craft. I was really afraid to do that.

Afraid of what, exactly?

WINFREY I was afraid of making a fool of myself! (Laughter.)

NICOLE KIDMAN (Big Little Lies, HBO) That’s every day.

REESE WITHERSPOON (Big Little Lies, HBO) What are you talking about?! The Color Purple is so amazing.

WINFREY When was that? That was like 30 years ago now. And let me tell you what actually made me even more intimidated: I just finished doing a film with Reese and Ava DuVernay and Mindy Kaling [A Wrinkle in Time], and I just happened to ask Reese, “How many films have you done?” And you said, “Oh, honey child …” (Laughter.)

WITHERSPOON Do you all know how many movies you’ve done?

WINFREY You said, “I don’t know, 100 or so.” I was thinking, “Oh, God, I hope she doesn’t ask me because my number will be like, five, maybe?”

CHRISSY METZ (This Is Us, NBC) Oh, I’ve got you beat. I’ve done maybe one independent movie.

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Reese Witherspoon can claim many titles: Oscar-winning actress, founder of clothing and lifestyle brand Draper James, voice of Rosita the pig in December’s animated feature Sing, star and co-producer of HBO’s February miniseries Big Little Lies, and mother of three, to name just a few. But on the night of October 2, she was, first and foremost, a Dolly Parton fan. As the country legend wrapped up the second leg of her Pure & Simple tour, Witherspoon and her friends belted out hits along with the rest of the nearly 18,000-strong sellout crowd. The following afternoon, Parton called Witherspoon to talk about being a “true Southern girl,” standing up to “bull donkeys,” and knowing exactly how much to give—and not to give—to “creative vampires.” Unsurprisingly, the admiration between the women is mutual.

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Reese on her inspiration: “When I was probably 5 years old, I wanted to be Dolly Parton. I was skipping around the blacktop at school by myself, and my P.E. teacher said, “Why aren’t you playing the game [with the other kids]?” I said, “Well, I’m not going to play the game because, Ms. Wright, I’m going to be Dolly Parton when I grow up.”

Reese on choosing who she works with: “I think that’s another good part of getting older. I’ve realized that life is too short to spend my time with anybody who doesn’t appreciate me, treat me with respect, or bring value to the relationship. I’m much more confident now, and I feel like I have the ability to say, “Nope, I don’t want to work with that person.”

Reese on her clothing line, Draper James: “It’s a new chapter for me starting a business, going around passing the hat, and promoting it all over the place. It’s a different experience, but I’m enjoying learning something new. I’ve been acting for about 25 years, and I still love it, but I like the challenge of trying something else too. I find there are a lot of people talking about New York and Los Angeles, but there’s a whole world out there in between, and that’s who I like to tell stories about and make products for – people who love the life they have and have a sense of style that’s uniquely their own.”

Reese on being a working mother: “I’m just trying to hold on, trying to make it through. My older kids help with the little one. It’s nice to have a big family.” “My mom worked, and I think it’s good for kids to see women working and being successful. I think it’s going to make them hard workers because they see that I don’t get much sleep. But I love what I do. I want them to grow up with passion. This is the one life you get, and you have to live it to the very end.”

 

December issue of InStyle, available on newsstands and for digital download Friday, November 11th.

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Reese Witherspoon was frustrated. It was 2011, and the screenplays coming across her desk had one bland female character after another. Defined as wives or girlfriends, they were nice, respectable and, for an actor interested in character work, boring. She was drawn much more to the protagonists of the novels and memoirs she curled up with at night.

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“My husband said, ‘Honey, you read more books than anybody I know. Why don’t you just option some and turn them into movies?’ ” Ms. Witherspoon recalled in a recent interview in Santa Monica, Calif.

In short order, she teamed up with producer Bruna Papandrea, launched an independent production company called Pacific Standard, and went on the hunt for challenging female characters. The pair quickly demonstrated that they could sniff out best sellers. They scooped up their first two books—Cheryl Strayed’s memoir, “Wild,” and Gillian Flynn’s thriller, “Gone Girl”—before they were published. In July 2012, just five months after the company was launched, the books hit No. 1 on the New York Times best-seller list at the same time—in the nonfiction and fiction categories, respectively. Together, the films earned three Oscar nominations and grossed more than half a billion dollars.

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For THR’s exclusive photo portfolio, A-listers — Reese Witherspoon, Taraji P. Henson, Dakota Johnson, Lupita Nyong’o, Elizabeth Olsen and Kirsten Dunst — pose with the beauty experts who get them red-carpet ready.

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Rese Witherspoon’s friendship with makeup artist Molly R. Stern began with a pair of leather pants.

“It was the ’90s,” said Witherspoon of the first time that she and Stern met. “I was being zipped into a pair of leather pants — and Molly was doing my makeup — and the stylist zipped me into the pair of leather pants and ripped my skin.”

“I nurtured her,” added Stern, who has been so close with the actress since the traumatic event that even her husband has a nickname for Witherspoon.

As one of the duos featured in this year’s THR Beauty Issue, Witherspoon and Stern go on to discuss not only their friendship, but also Stern’s best-kept beauty tips and their favorite of the award-winning actress’ red-carpet appearances.

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Just a few years ago, Reese Witherspoon was pitching a new movie to seven studio heads and requested an extra 30 minutes with each executive to ask one question: What do you have in the works for women? “Only one studio was developing something for a woman in the lead,” Witherspoon, 39, recalls. “They said, ‘We’re happy if you bring us something, but it’s not a part of our development.’ ” Stunned, Witherspoon started obsessing over the deficit—bringing it up at dinner parties and business meetings, to a chorus of women saying, “We know!” Yeah, I’ll bring you something, she decided.

So in 2012, Witherspoon cofounded a production company, Pacific Standard, with producer Bruna Papandrea; the duo began buying up books and scripts with female protagonists to turn into films and TV series. And by 2015, Witherspoon found out just how winning her company’s by-and-about-women formula could be. Wild and Gone Girl, its first two films, featured women not as sidekicks or arm candy but as leading ladies who go through unique personal journeys. Stars Rosamund Pike, Laura Dern, and, yes, Witherspoon herself were all nominated for Oscars—and the films banked more than $400 million worldwide at the box office. With her producing and acting credits, Witherspoon landed on Forbes’ list of highest-paid actresses and on Time’s 100 Most Influential People list. Now she’s breaking into a full-on sprint toward equality: Pacific Standard has 32 projects in the works that put women front and center. “Reese gave me the opportunity with Hot Pursuit where I was producing, where I was a main character, where I got to play a strong, Latina woman,” says Sofía Vergara. “It’s amazing, Reese is such a tiny little thing, but she’s such a strong woman—she knows what she wants, and she gets what she wants.”

With her producing business booming, Witherspoon felt she could take on another new challenge this year: a fashion brand. She launched Draper James, a Southern-inspired clothing and home line, with a flagship store in Nashville. Lest you think she’s superhuman, though, she hasn’t taken an acting gig in over a year, so she could spend time with her husband, Jim Toth, and three kids, Ava, 16, Deacon, 12, and Tennessee, 3. (And yes, they are the cutest.)

Of course, none of this surprises me. I’ve known Reese for several years. She’s always been an incredible supporter of women and their work, mine included. After we were introduced by a mutual friend, she hosted a screening of my documentary Miss Representation back in 2012. Then, this year, she helped spread the word about my organization, The Representation Project, and our #AskHerMore initiative: Together with women on social media, we succeeded in encouraging reporters to go beyond the traditional “Who are you wearing?” questions and to ask actresses about their accomplishments on the Oscars’ red carpet. As Papandrea says: “Someone once said to me, ‘The two features you want in a friend are interested and interesting.’ She’s both.” Witherspoon is indeed a Woman of the Year.

Jennifer Siebel Newsom: I’m so proud of you. Congratulations on being named one of Glamour’s Women of the Year.
Reese Witherspoon: Thank you.

JSN: Well, let’s get into this. You were raised in the South, where things can be traditional, but you’ve grown into this ­forward-thinking voice for women. You’ve said that was the result of having a powerhouse mom (a nurse) and grandmother.
RW: Uh-huh. I’d always ask my grandma, who was so, so smart, why she didn’t work, and she would explain that her parents didn’t approve of her working after she had children. She didn’t feel like she had choices. And I witnessed it all firsthand. Growing up in the South, it was very patriarchal. When I applied to Stanford, I was told by a [male] college counselor, “You’re never gonna get in, don’t bother. They don’t want you.” I said, “I’m going to try.” And I got in! But I wouldn’t be the woman I am if I hadn’t had that conflict to overcome. It has given me an underdog feeling all my life.

 

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