The one and only time Shailene Woodley beams during our time together – a long conversation over Zoom, on a bright weekday morning – is when my young son sneaks into the room in which I’m bent over a laptop, points at the stranger appearing on-screen, and asks, not quietly, “Who’s that?”
There is nothing to do but introduce them.
“Nicholas,” I say. “This is Shailene.”
“Shailene,” I say. “This is my son, Nicholas.”
Remarkably, my son, understanding these formalities, offers a decent “Hello.” And Woodley, grinning, says “Hiiiiii!” in reply, pulling that vowel along sweetly, before adding, more graciously than is necessary: “So cute!”
My son is five years old. He is an expressive talker, and mostly he listens to adult direction, though his mum and I are yet to find out how he might act under pressure, and there are times when he will say “no” at the hint of an activity he doesn’t want to do – will “never” do – and then, you understand, a battle begins.
I mention this because Woodley was five years old, too, when she began acting, mostly in commercials in the early years. And when I imagine my son in those kinds of situations, surrounded by adults he doesn’t know – adults who might ask him to stand a certain way, or speak a certain way, perhaps kindly at first, but then, if things don’t go so well in the beginning, perhaps less kindly – I wonder: how? How did Woodley do it? And not only that, how did she go on to maintain a significant Hollywood career, appearing in clever films and TV series, bringing to them the kind of experience you develop from having acted for most of your life?
Woodley turns 30 in November. “This year I will have been acting for 25 years,” she says. “Which is a really fucking long time.” Woodley took up commercials the way another kid might take up tennis, and what began as a hobby gradually grew into the thing that “dominates most of my time”. In her breakout role, in the The Descendants, from 2011, she played George Clooney’s emotionally wayward daughter. She has since starred in a series of big-news productions, including the unravelling HBO drama Big Little Lies, for which she was Emmy and Golden Globe nominated, alongside Reese Witherspoon and Nicole Kidman, and the 2014 tearjerker The Fault in Our Stars, in which she played a cancer patient struck down by romance as well as terminal illness. In her latest film, The Last Letter from Your Lover, adapted from the Jojo Moyes novel, she plays a glamorous 1960s housewife who, after a car accident, forgets and then gradually recalls an affair she is having. Woodley accepted the job because she felt close to the film’s director, the American actor Augustine Frizzell. “We connected on an emotional level,” she says, of their first meeting. “And months later I get an email: ‘Hey, Augustine is directing a film.’ I said yes before I’d even read the script.”
Many of Woodley’s decisions are made on a similar gut-instinct level, which might be her first lesson in surviving Hollywood: feelings matter, act on them. In The Last Letter from Your Lover, Woodley’s character must turn inwards to grasp who and what she loves, even though the discovery might uproot her life. Woodley lives like this, too: on a quest for personal truth. “Authenticity is my lurve language,” she says. “I don’t care if you give me an ugly side of yourself or the mean side of yourself, whatever, just be authentic about it.” Woodley grew up in suburban California. She also grew up with psychologists for parents. Kate Winslet, a close friend of Woodley’s, told me, “What I was struck by most in meeting her was this sense of acceptance of self, which I certainly did not have when I was her age, and which we very seldom see in young actors today, because there is so much pressure, and somehow Shai has been able to sidestep all of that, just by remaining true to herself.”
Woodley met Winslet in 2013, while the pair filmed the dystopian blockbuster Divergent, in Chicago. Winslet was 22 weeks pregnant with her son, Bear, and she became a mother figure to Woodley, too. “You know, Kate’s been a huge influence on my life when it comes to staying 100% true to who I am,” she says. The pair maintain an active long-distance relationship. “I’ll call her and say, ‘I’m falling off the ledge’ or ‘I’m feeling insecure about this’ or ‘I don’t know what to do about that’, and she talks me down.” Often they’ll speak late at night – transatlantic “self-help talks” – about the things going on in Woodley’s life. “It could be anything: a heartbreak, extreme heartache… Or the feeling that a story ran where someone twisted your words and you’re reading something online and suddenly the whole world thinks you’re a certain way that you’re not. And the panic from that, the panic that can come from, ‘Oh, my God, people think I’m this kind of person and I’m not that kind of person’ – that’s pretty extreme.” (These lines, when she first delivers them, do not feel like a threat, but later they make me think.)
Woodley describes Winslet as “my guardian angel”; without her, she says, “I don’t know I’d still be an actor the way I am today; I wouldn’t be able to cope emotionally with the extreme waves this industry can bring.” This marks Woodley’s second lesson in survival: ask for help, glean from the experienced people around you whatever advice you can. For that reason, Winslet isn’t Woodley’s only mentor. “The first project I did of substance was this small, tiny movie” – A Place Called Home, from 2004 – “and Ann-Margret played my grandmother. She gave me these incredible anecdotes, incredible little doses of wisdom.” Woodley had no idea who Ann-Margret was – “I was told, you know?” – but she listened anyway, rapt. “And from there I did a TV show” – The Secret Life of the American Teenager – “and Molly Ringwald took me under her wing, showed me the ropes, how to navigate fame at a young age. And she passed the baton to George, and George Clooney becomes like a father figure to me, and helped guide me and imparted his wisdom and knowledge.” In the legal drama The Mauritanian, released earlier this year, Woodley appears alongside Jodie Foster. “And now it’s Jodie!”
When I ask why her co-stars seem drawn to offer advice, she shrugs, then says, “I really do feel that the divine grace of something in this universe has given me these people to be my guides.” (Winslet suggests, “Shai’s just always been so fascinated by how other people have handled different and sometimes challenging aspects of their own lives…”) “The people I’ve named,” Woodley continues, “we love each other. We see each other as people – as real, breathing, emotional creatures outside the characters we play. And you want to protect that. You want to make sure people don’t feel alone in the world. You want to make sure people feel seen and heard.”
Throughout her career, Woodley has had an on-again, off-again relationship with Hollywood. She describes the film industry as “a disastrous chaos” that is sometimes better avoided, and there have been years-long periods when she’s decided not to act. When she was 18 and working on The Secret Life of the American Teenager, she lived alone in a mountain cabin so remote “I had to drive a couple of miles to the end of the road to get phone service.” (She recalls the period as “magical”, though “looking back, I don’t know how I managed to do that and not not turn up to work.”) During her early 20s, she gave up a permanent address and travelled nomadically from set to set, couch-surfing with friends in off periods. Once, she told the people around her that she planned to spend a couple of months backpacking around New Zealand, and instead disappeared from view by hiding in LA.
“You know, there’s this theory in Hollywood that when you’re hot, you’re hot, you’ve got to keep working, otherwise you’re not going to be hot any more, and nobody’s going to care…” She tuts. “I always thought that if you’re good at what you do, you’re going to work.” As a young actor, she says, “you audition almost every single day. You get told ‘no’ a thousand times. You get one yes and it’s soooo exciting. And then you get told ‘no’ another thousand times.” In her teens, Woodley was told acne might prevent her from securing roles, and “I shouldn’t audition any more.” It was later suggested she begin birth control as a skincare treatment and that she become “more cosmopolitan – to dress a certain way, to think a certain way, to not say certain things.”
At the time, comments like these didn’t affect her. “I was so strong-headed and free-willed, so rooted in the core of who I was,” she says. “But in my mid-20s I went through a couple of years feeling insecure about the choices I was making, believing the opinions of others a little bit too much, not staying on my path.” She began to compare herself to her peers: “I had a couple of years where comparison was really detrimental to my mental health”. She describes the period as being full of “massive insecurity and self-doubt”. Often small worries would grow out of proportion: “Am I eating the right fucking breakfast foods? Is this what I want to do? Am I this enough? Am I that enough?” Until then, “life had felt good, pretty solid, and I’d been unwavering in who I am, and then…”
While Woodley was working on the Divergent trilogy she became seriously unwell, a fact that remained private until last year. “You know, health is one of those things where, unless something is very visible, unless you can see someone has a broken leg, it’s such a personal battle, it’s such a private battle.” She won’t reveal what happened: “All I’ll say is that I feel so grateful to be alive.” Also: “It’s weird to have huge movies coming out and premiering while you’re laying in bed not able to move going, ‘Oh, fuck.’”
Life seems less stressful now. During the pandemic, she met and became engaged to the American football star Aaron Rodgers. (At first, Woodley didn’t know who he was; she said recently, “I never thought I’d fall in love with someone who throws balls for a living.”) She asks, affably, that we don’t discuss the relationship. “We’re trying to keep it as private as possible.” Though she will talk about love. “I went camping in the desert recently,” she says, “and there were these giant, giant canyons around me, and it’s the purest form of love I can experience, looking at these canyons. It’s the same type of love I experience when I look at a lover, or my mum, or my dog, and I guess at certain times I feel it with myself – a feeling of connection.”
For expressions like these, Woodley can come off as a bit of kook. She is a press mainstay for revealing unusual personal habits: whitening her teeth with sesame oil; sunbathing naked in order to “give my vagina a little vitamin D”. Every morning she wakes up and sings. She has been described repeatedly as hippy-ish, as though she has emerged from another, more grounded time. “I mean, I used to get offended by that. But now I’m just like, ‘Great, you want to call me a hippy? So many things about the hippy movement were fucking beautiful, I’m all about it.’” Throughout her career she has highlighted significant environmental issues; in 2016 she was arrested for protesting the Dakota Access Pipeline. (She refers to the ocean, where she spent part of 2019, courtesy of Greenpeace, as a “she”.) “When I was talking about these things 10 or 15 years ago, it was before people knew what environmentalism was. The most environmental thing you could do then was recycle. There wasn’t a lot of narrative around these things. So of course you’re going to be ostracised in some way, be labelled as ‘other’, because it’s not mainstream.” She accepts, and is grateful, things have changed. “Now? Every single fucking influencer or model or CEO is talking about this! Look, I don’t take offence at being called ‘The Hippy of Hollywood’ if it means one or two people are going to learn some things.”
It is this version of Woodley that seems most true: the hippy-ish, not-mainstream Woodley, a person who bothers about things going on in the world and the people within it – who also acts. Winslet told me: “Shai has an awareness that sometimes paying attention to the life experiences of people around you, who have already gone through certain chapters in their life” is valuable, which you might wag a cynic’s finger at, labelling it “actor speak”, but here seems genuine. “For me, the way I grow as an actor is by studying other people in the flesh, in real life,” Woodley says. (She claims not to have watched many films, which she assumes provide inspiration for other actors.) Once, while travelling in her 20s, she fell asleep in a train cabin in Italy, “and somebody comes into the cabin and tries to steal the backpack out of my hands, and I’m wrestling with this person…” To her, the experience was thrilling, not terrifying, and helpful as a truth to be witnessed. “One day in the future, perhaps I’ll play a character where I’ll need to call upon that memory. And I’ll understand so intrinsically how that needs to be played because I’ve seen it in real life. I’ve lived it. I’ve looked into that person’s eyes.”
Last Letter from Your Lover is in UK cinemas on 6 August
Photographer’s assistants: Caroline Salazar, Sebastian Keefe, John Batchine; styling by Alexandra Mandelkon at The Wall group; hair by Adir Abergel for Virtue Labs; makeup by Sabrina Bedrani for Dior Beauty at The Wall Group; manicurist Betina Goldstein for Chanel Beauty at The Wall Group