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‘I love nothing more than making people cry’: author Cheryl Strayed on her hugely moving TV show | Television

In 2011, a little-known fortysomething author called Cheryl Strayed was about to become huge. She had just sent a copy of her soon-to-be-published memoir, Wild, to Oscar-winning Hollywood star Reese Witherspoon. It tells Strayed’s story about hiking the Pacific Crest Trail, while processing the turbulent events of her younger life that had taken her there – childhood abuse, her mother’s death from cancer, her heroin addiction and the breakdown of her marriage. Witherspoon read it within 48-hours and set up a call; she desperately wanted to bring the story to the big screen with her newly founded production company.

“It was exciting talking to Reese Witherspoon but I didn’t think: ‘Oh my God, whatever she wants – the answer is yes,’” says Strayed, now 54, from her LA office. “But we had this wonderful, deep conversation for about an hour on the phone. I could tell by the way that she spoke to me with such vulnerability and candour, that she was somebody I could trust. I wasn’t wrong about that.”

The memoir became a New York Times bestseller and Oprah chose it as her book of the month. The film, in which Witherspoon played Strayed alongside Laura Dern as her mother, went on to pick up two Oscar nominations in 2015 and inspired a generation of women to lace up their boots, get out there and scream atop a big rock. Dern, Witherspoon and Strayed got on so well that after Wild’s London premiere, Strayed ended up suggesting they adapt another of her books, Tiny Beautiful Things. They agreed and today the three women are friends. “It started as a conversation all those years ago and here we are today. In my memory at least,” she warmly laughs. “I want to talk to Laura and Reese about this and see if they remember the same thing.”

Reese Witherspoon in Wild.
‘I could tell by the way she spoke to me that she was somebody I could trust’ … Reese Witherspoon in Wild. Photograph: Fox Searchlight Pictures/Sportsphoto/Allstar

Released on Disney+ this week, Tiny Beautiful Things is a gorgeous drama. Produced again by Witherspoon’s company, Hello Sunshine, it is at once heart-wrenching and a balm for the soul – with spurts of smart humour. It follows a frazzled writer in her 40s, Clare, whose life is unravelling. She is undergoing couples therapy with her husband, Danny (and accusing him of sleeping with the therapist), she can’t have a conversation with her teenage daughter Rae without doors being slammed and she is fired from her job in a care home for sleeping in a resident’s spare bed after a big night out. But look closer and it is the ghosts of Clare’s past – her absent father, her dead mother, her estranged brother – that are unsettling her as she tries to resolve unfinished emotional business. One way she tries to take back control is by becoming an anonymous online agony aunt, Dear Sugar, calling on her own experiences to help others.

It is, of course, inspired by Strayed’s real life. After her debut novel, Torch, was published in 2006, Strayed continued to work as a waitress and “a million different things”. She took over the Dear Sugar advice column in The Rumpus in 2010, despite it being unpaid and having barely any readership. She wrote her replies as personal essays with unflinching honesty and striking prose. “There was no good reason to say yes, except I felt this spark within me,” she says. “I didn’t care if I was qualified or not, because I didn’t believe that anyone was qualified. I realised that I had been training for this job all of my life.” The column became an internet hit and she finally revealed her identity in 2012, then turned some of the posts (one of which asked “WTF, WTF, WTF?”) into Tiny Beautiful Things, which went on to be a bestseller. It has also since spawned a podcast series and a stage production: “It ended up becoming one of the most meaningful things of my life. I’m still Sugar.”

Strayed makes the point, though, that the TV series is a fictional work. “How about this woman we create isn’t me, but she had that same stuff happen to her in the past and she took a different path to me as an adult,” she said from the off, “so we get to do whatever we want. We get to be in the land of fiction … but the show is still absolutely full of my heart.” She created Clare, who is played by Sarah Pidgeon in the flashbacks to her younger self that frequently accompany her attempts to offer advice to readers and played by Kathryn Hahn as her current-day incarnation. The latter’s performance is so good it absolutely steals the show.

“Everybody always says to me: ‘Oh my God, I love Kathryn Hahn!” Strayed proudly says of her masterstroke casting. “Tiny Beautiful Things is known for making people cry – there is nothing I love more than making people cry – but I also like to make people laugh. When Kathryn said yes, we knew we had somebody who could not only capture all of that, but also expand on it, because she is such an extraordinarily smart, subtle, funny actor.”

Kathryn Hahn in Tiny Beautiful Things.
‘Everybody always says to me: “Oh my God, I love Kathryn Hahn!”’ … Hahn in Tiny Beautiful Things. Photograph: Elizabeth Morris/Hulu

The biggest part of Strayed’s story that she always has, and always will, include in all of her projects is her mother, Bobbi Lambrecht. Clare’s mother Frankie (Merritt Wever) dies in the series the same way Bobbi did – within six months of a lung cancer diagnosis when she was only 45 years old. Bobbi raised Strayed and her two siblings, Leif and Karen, without their father and on a shoe-string budget. In the opening episode, Clare recalls the Christmas she turned her nose up at a coat her mum had saved up for months to buy her. “What would you tell your 20-year-old self?’ a woman asks Clare, under her Sugar pseudonym. “Your mother will be dead by spring and that coat will be the last gift she ever gave you,” she replies. “When a gift is given, say thank you.” The regret Clare still feels is painful to watch.

“My mother has been dead now for 32 years; she was only alive for 22 years of my life,” says Strayed. “The most powerful thing I can do with my grief, which is ultimately just my gigantic love for my mom, is to tell stories about it and share my feelings about this experience with the world so that other people feel seen and recognised.” She refers to a piece of advice she gave to a man whose son was hit by a drunk lorry driver. “I can’t live without my child. How can I go on?” he asked. “I said the only thing we can do when we lose somebody who is essential to us is take the ugliness of that loss and make something beautiful. And Sugar is my beauty that I made of my mom’s death. Sugar is the beauty I made of my sorrow. It’s beyond catharsis.”

Another of Strayed’s relationships retold with rawness in the adaptation is that with her brother. In flashback, we see the younger version of Clare go to find her brother Lucas (Owen Painter), who was too scared to see his dying mother in hospital and blame him for being the reason neither of them were with her when she died (this is very similar to what happened in real life). Grownup Clare’s relationship with Lucas remains complicated – the hot glue of anger, shame and guilt sticks for life. “After my mom died, my family fell apart. And that included my siblings,” says Strayed, who is still somewhat protective of their privacy. “I love them very much and they love me, but our relationship has been difficult, since our mother died, in so many ways. They’ve struggled just like I’ve struggled and sometimes that has led to a sense of distance or concern. And I really wanted to put that into this story.”

Cheryl Strayed, centre, with Laura Dern, left, and Reese Witherspoon who were both executive producers of Tiny Beautiful Things.
‘It started as a conversation all those years ago and here we are today’ … Strayed, centre, with Laura Dern, left, and Reese Witherspoon who were both executive producers of Tiny Beautiful Things. Photograph: Barry King/FilmMagic

Strayed is now a mother of two – a son, Carver, 18, and a daughter, Bobbi, 17 (named after Strayed’s mother) – and says she doesn’t like being “too autobiographical” when it comes to her children. Of course, Strayed still takes inspiration from arguments and admits that the writers room (made up mostly of women in their 40s and 50s) knew that Clare having a teenage daughter was “just such great fodder for comedy and drama”. A scene in which a video of Clare shouting at a schoolgirl for having a threesome with her daughter goes viral is just one excruciating hoot.

And what about Clare’s second husband, Danny (Quentin Plair), and Strayed’s second husband – documentary-maker Brian Lindstrom, who she married in 1999 – are there any juicy parallels there? She doesn’t expand beyond them both being second marriages, but does say she uses her fictional couple to examine the realities of long-term relationships in middle-age: “They’re finding the ground is shifting. Your 20s are that time when everything’s happening, but in your 40s and 50s, especially with a child about to leave the nest, [Clare and Danny] are starting to say: ‘What is next for me?’ And we’re not sure if they are going to include each other in that next chapter.”

Strayed admits that she was scared of being so big-hearted when she became Sugar because “I’m not like a snarky hipster”. But this series works so well for the same reasons that people fell for Sugar in the first place: “What I realised is that people are actually really hungry for sincerity, for somebody to say: ‘It’s OK. You are loved. I do care about you. You’re not alone.’”

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