Lily Allen’s Second Act

The British singer, now sober, has a new life in New York and a new string to her bow: acting. By Desiree Ibekwe. Photographs by Ellie Smith

The singer and actor Lily Allen photographed in London in July.

Lily Allen didn’t know why she agreed to be interviewed for this article.

On a recent morning, sitting outside a London cafe, the British singer said she had paused earlier for a moment of reflection. “I was like, ‘Why am I doing this?’” she said. “I sort of wonder why I put myself in these situations and open myself up to criticism.”

Allen, 38, hypothesised that the answer might be narcissism or her resignation to the requirements of being in the public eye. “It’s been my life since I was, like, 18 years old,” she said.

Since Allen burst onto the pop music scene in the mid-2000s with lilting reggae-infused tracks like “Smile”, her relationship with the press has been fraught. She has always been outspoken — in her lyrics, in interviews and on social media — and for many years she was a fixture in Britain’s tabloid newspapers. In 2009, she obtained a court order to stop paparazzi following her around London. “It’s not a very nice feeling,” she said of that kind of attention. “Especially when you’re in your early 20s and you’re still trying to figure out who you are in the world.”

Now, Allen lives in New York, where she largely goes unrecognised. She was back in London because she has also left music behind — at least for now — and turned her attention to acting instead. Allen just finished playing a lead role in a West End revival of “The Pillowman”, the 2003 play by “Banshees of Inisherin” writer and director Martin McDonagh.

“I still get to play with the human experience,” she said of this career transition, “but I don’t have to put my heart on my sleeve as much” as in her — often very personal — songs.

Allen’s mother is a film producer and her father an actor, but as a teenager she was drawn to music. When she was 19, in 2005, she signed to the Regal/Parlophone label and built a following on the then-nascent social media site MySpace. According to Michael Cragg, who recently wrote a book on British pop music, the music scene at the time “was kind of mired in ‘The X Factor’ and TV talent shows.” The consensus, he added, “was that pop needed a bit of a kick up the bum”.

Clad in prom-style dresses, chunky gold jewellery and sneakers, Allen was a new kind of British pop star. With a London accent, she sang her own funny and provocative lyrics about messy relationships, sex and self-loathing. “A young woman singing and presenting themselves in that way felt very exciting,” Cragg said. Her first two albums — “Alright, Still” and “It’s Not Me, It’s You” — were commercial and critical successes, but the making and marketing of a third, “Sheezus”, in 2014, was more fraught: in interviews, she has described having an “identity crisis” at the time, as she tried to be both a pop star and a new mum. In 2018, Allen’s next release, “No Shame” — a low-key record that addressed her divorce and feelings of isolation — was nominated for the Mercury Prize, but Allen has since become disillusioned with the music industry, she said. “It’s so competitive, it’s so rooted in money and success and digital figures,” she added. “I’m just not interested in doing any of that.”

At around the same time, she also changed her relationship to alcohol and drugs. “From 18 to about four or five years ago just feels like a bit of a haze, because I was literally just off my face the whole time,” Allen said. “I was using fame as well — that was an addiction in itself: the attention and the paparazzi and the chaos.” Allen’s “four year sober birthday” fell on the date of this interview, she said, and it seemed that chaos had abated. Three years ago, she married “Stranger Things” actor David Harbour, 48. Her life in New York with him and her two daughters from her previous marriage was “pretty leisurely”, she said.

So when she was approached about an acting role in the West End show “2:22 A Ghost Story”, she “was like, ‘No, I don’t act and I live in New York, so no thanks’”, she said. But Harbour convinced her to take the gig, and it earned her a nomination in the Olivier Awards, Britain’s equivalent to the Tonys or the Helpmann Awards.

In “The Pillowman”, Allen plays Katurian, a writer living in a totalitarian state, who is questioned about a string of child murders that remind authorities of her fictional stories. Like much of McDonagh’s work, it’s as dark as it is comic. Allen said she saw a through line between McDonagh’s “dark and sick humour” and the lyrics of the songs she used to write. In rehearsals, she added, “I would say things that people might ordinarily be shocked by, and you look at Martin and he’d be smiling.”

Allen’s turn as Katurian is the first time the role has been played by a woman, and her casting gives Katurian’s interrogation scenes, in which she is verbally and physically abused by two detectives, a different weight. “The play really is about patriarchal brutality,” said Matthew Dunster, the production’s director. “I said to Martin, ‘This is going to be really difficult for audiences to take, this slight woman being treated to brutally so early on in the piece’, and Martin said, ‘Isn’t that the point?’ ”

Dunster also directed Allen in “2:22 A Ghost Story”, and he said he had seen her grow as an actor. “What was thrilling to me was to see her taking ownership of her own process,” he said.

Allen said that once back in New York, her priority would be settling her two daughters into middle school, but she had also applied for acting courses. One day, she said, she hoped to land lead roles in films and television. But, for now, she added, she was leaving herself open “to any opportunities that come my way”.

This is an extract from an article that appears in print in our ninth edition, Page 28 of Winning Magazine with the headline: “Lily Allen's Second Act”. Subscribe to Winning Magazine today.