Can Lola Young Make It Big Without Breaking?

An aspiring young pop star today can be a lot of things: self-loathing, self-aggrandizing, sexually frank, romantic, realistic, irreverent, evasive and in-your-face.

Lola Young, the diaristic British singer behind the hit “Messy,” is all of the above.

At 24, after nearly a decade of trying to make it, Young has finally arrived — on TikTok, the radio and festival stages. Still, the ride is just beginning.

We followed the pop-soul singer across Paris and London one weekend in July for a taste of what it takes.

It was a summertime Saturday in Paris, but Lola Young was about ready to go home.

The scene, by now, had become routine to the 24-year-old singer: a nondescript trailer behind layers of barricades, where, for months — from Indio, Calif., to Gdynia, Poland — Young had warmed up and waited before greeting growing music festival crowds that were increasingly singing along to her off-kilter pop songs.

The vibes at the previous day’s set in Switzerland had been slightly off. A night spent crossing the border in a 16-bed tour bus hadn’t provided much of a reset. Young’s manager, Nick Shymansky, could sense her edginess, having become ever-attuned to the subtle fluctuations of her brain chemistry since they began working together when she was a teenager.

“She’s melancholy tonight and I can see it,” he whispered outside her trailer. “I don’t know if she knows it, but I feel it.”

Still, Young and her team knew she had to turn it on. A coveted evening slot at the French edition of Lollapalooza was another in a long string of “I made it!” moments that she had been chasing most of her life. A trip back to her native London — and a few much-needed days off — were scheduled for the next morning. But it was time to go to work.

Heading Home

“It just depends on the day,” Young, still contemplative but slowly brightening, said the following morning on the train back to South London. “Some days I wake up and I’m just pinching myself,” she said. “There are other days I wish I wasn’t pinching myself.”

She continued haltingly, not wanting to sound ungrateful. “It’s hard getting a small — it’s not really a small taste, it’s quite a real taste — of some levels of fame, success and money, and all the glitz and glamour that you think you wanted,” Young added in her hallmark tumble of an accent. “I’m [expletive] good at what I do, I worked really hard to be here, some people would die to be in my position and some days I hate it. That doesn’t feel fair.”

Since breaking out with her too-much anthem “Messy,” a radio smash that grew from TikTok to the Billboard charts, Young is vying to become the latest in a growing lineage of young female singers for whom chronic disarray is both a selling point and a relatable, teachable moment, not their ultimate downfall.

As a songwriter whose chief muse is torment (self-imposed, biological, inflicted by rotten men), Young recalls the world-building rawness of recent forebears like Billie Eilish and Chappell Roan, who have studiously taken the previous generations’ sensations-slash-casualties — Alanis Morissette, Britney Spears, Sinead O’Connor, Amy Winehouse — as legacies worth building on and correcting.

But given Young’s history of substance abuse and mental illness (she was diagnosed as a teenager with schizoaffective disorder and ADHD), the balancing act is a daily, if not hourly, undertaking. “I smoke like a chimney / I’m not skinny and I pull a Britney / every other week,” she sings on “Messy.”

Since 2017, Young has also worked closely with Shymansky, who managed Winehouse beginning when they were teenagers, up until he gave the retro-soul singer an ultimatum ahead of her breakthrough album “Back to Black”: Get clean or do it without me.

Winehouse responded by writing “Rehab,” which went platinum, and winning six Grammys; she died of alcohol toxicity in 2011, at 27.

“The whole thing’s completely complex, but of course this is like a dream moment to me,” Shymansky, now 45, said of his second chance with Young. “I’m seeing this person that I deeply care about, that I feel is so special, and I’m getting to be the person I wish I could have been.”

“It’s not going to be perfect,” Shymansky added, “but I believe she can work with her mental health stuff, work with her demons, I believe she can grow, be huge and I believe she can have it all. I want her to have it in 2025 in a way that Amy could never have it.”

That means riding the rocket ship of fame as slowly and deliberately as possible, even as Young also attempts to seize her moment with a new album, “I’m Only Fucking Myself,” out Sept. 19.

Written amid the yearlong rise of “Messy” and Young’s simultaneous attempts to get sober — “I’m a dumb little addict so I’ve been tryna quit the snowflake,” she sneers on the bouncy pop-rock singalong “Not Like That Anymore” — the album catalogs her “crawling out of my own self-sabotage,” she said, which she has often cut with eroticism and black humor.

“It’s funny, because you get to a moment where you go, Oh, [expletive], like I’m kind of experiencing what I’ve been longing to experience for a while and it hits you in the face,” Young said before her Lollapalooza performance. “And then what?”

Hard Shell

The daughter of a white British mother and a Chinese-Jamaican father, Young grew up fast in the Beckenham area of southeast London.

One of four sisters, she has the occasional brashness of a compensating street kid but can just as quickly retreat into a mopier, ruminative mode, the kind of youthful searcher likely to buy — and then reject — a book called “The Meaning of Life.”

Part Bratz doll and part Hello Kitty, she molts styles by the day or week, but generally favors large hoops, facial piercings, flashy tooth jewelry and a “full-beat” face, complete with exaggerated falsies and drawn-on freckles.

In conversation, Young refers frequently to past scraps, emotional and physical — slapping at a teacher who told her she shouldn’t rap, squabbles over boys — but increasingly sees that side of herself as a defense mechanism, a hard shell formed to protect her roiling, tender interior.

Violet May, a friend from childhood, recalled their shared youth as dark and chaotic mayhem usually played off as high jinks. “We were both traumatized,” she said over shawarma, as Young enjoyed some homey normalcy at May’s Brixton apartment. “Because we were grown for our age, we were experiencing some stuff that was too, too much.”

“We deserved to be a bit more sheltered, I think,” May added.

Young agreed. That said, it made for “bangin’ material.”

Dream Team

At 14, through a talent-seeking alumni network, Young enrolled at the BRIT School, a performing arts incubator attended by musicians like Winehouse, Adele and King Krule.

“That was intense to me, because it was like, well, there’s people who are just allowed to be themselves,” Young said of the culture shock. “I didn’t like that because I’d never been.”

Channeling her social anguish and burgeoning mental health problems into devastating acoustic ballads, Young began to record and perform constantly, drawing notice as a busker and on the local open-mic scene.

She knew music was her “calling,” she said, during one of her early trips to a studio, when someone remarked that recording the same section of a vocal over and over again was “so boring.”

“Oh God, I don’t find it boring at all,” Young thought. “A very simple realization, but also a realization that I could do this the rest of my life.”

Not long before she was diagnosed with her mood disorder as a teen, Young defeated some 9,000 entrants in the Open Mic UK contest with an original song, “Never Enough,” and the industry was starting to circle. At a South London showcase attended by every manager in town, Young met Shymansky, who had not worked directly with an artist since Winehouse’s death.

Shymansky had been scouting talent for a documentary he was developing with the director Asif Kapadia (“Amy”). “Lola had just got onstage,” Shymansky recalled. “She was mind-blowing, 16 and also like a sort-of comedian — really sad songs and then really funny in between.”

Back in Young’s dressing room after her set, the singer was skeptical as Shymansky pitched his project. “And then I found out that he used to manage Amy Winehouse and the tables turned,” she said.

As the pair continued to feel each other out, Young made the final call unilaterally. “She started introducing me to people as her manager,” Shymansky said.

Appropriately cowed, he brought on Nick Huggett, who had helped sign Adele, forging a dream team that portended a best-case scenario for Young’s career: She could be Gen Z’s Amy Winehouse, without the tragic ending, or its Adele, with plenty more edge. (Huggett later left the management team.)

Over almost a decade working together, their connection has sprouted wildly, with Shymansky doubling as a protective big brother, cool uncle, guidance counselor and bemused fogy as needed.

“There’s not five hours of my life I don’t get a [expletive] phone call,” he said. “And I’m happy to get a phone call. Even if she wasn’t an artist, she’d be one of the most interesting, brilliant people in my life. It’s a dream. And at times, not so much.”

Cracking the Code

Before “Messy,” Young’s career was a succession of almosts.

There were years of professional and personal uncertainty, tied in part to her drug use and manic phases of creativity, followed by deep lows. Signed to Island Records, she released a series of patchwork EPs around the Covid-19 pandemic and eventually, a 2023 debut album, “My Mind Wanders and Sometimes Leaves Completely,” that failed to chart.

The through line of her strongest work continued to be a plain-spoken, sometimes brutal self-assessment: a stream-of-consciousness, run-on download from a wonderfully erratic brain. These days, asked constantly about her knack for “honesty” in song, Young can only be incredulous. “I still don’t quite get it — what’s the other option?” she said.

But those around her, Shymansky especially, can sometimes wince at the levels of realness. “If you’re hearing the music, it’s equally playful and fun, but also in isolation, incredibly worrying and dark,” he said. “The idea is just trying to get the balance.”

Going into “This Wasn’t Meant for You Anyway,” Young’s breakout breakup album from last year, she had an epiphany. “I decided to write as if I was speaking to somebody,” she said — a casualness she had lost to self-doubt.

“A lot happened with my label, trying to find my brand, how I looked — and what happened in that process is that I started masking through a metaphor,” she said.

Young went through a similar process on social media, which eventually helped catapult her to real fame. To scroll her Tumblr, TikTok or YouTube from the bottom up is to witness a spaghetti-throwing experiment — awkward mess and a few things that stuck. “It’s like looking at a bad photo of you before you hit puberty or something,” Young said, cringing.

A few years ago, Shymansky brought on Lily West, a friend of his younger sister, to make honing Young’s visual persona fun, instead of a chore dictated by her label. They tried for years to “crack it,” West said, making amateur montages of couples in public, jumping on forced trends, filming bad dances.

Eventually, they happened upon a gimmick that worked, bringing attention to Young’s textured voice by putting her behind a huge professional microphone in unlikely locations (a swing, a canoe, a beach) and allowing her to sing live.

Young’s music began making its way to posts by influencers like Kylie Jenner, routinely reaching millions as the platform’s aesthetic evolved alongside them. Snippets of “Messy” became unavoidable, even jumping borders to X and Instagram, where users could not decide if they hated or loved the song’s unwieldiness, raising its standing. (Late last year, Young received another clout bump when she was featured on “Like Him” by Tyler, the Creator.)

“But I’m not a TikTok artist,” Young insisted. “I get insecure sometimes that I am, actually. I have to say it out loud.”

She and Shymansky agreed that the years it took them to bottle lightning made the eventual wins more fulfilling — and sustainable.

“It’s funny,” he said, “we’d have done anything at the time to have a hit, to have a moment, and you look at it now and you think, actually, I’m so sure it wouldn’t have worked out as well if it happened then.”

Work in Progress

Following up a smash isn’t easy for anyone. For Young and Shymansky, the stakes are even higher.

In November, ahead of recording her new LP at Electric Lady Studios in New York, Young entered a treatment center for five weeks to address her dependence on cocaine. By the New Year, she was back to the industry rat race, delivering a surprise star turn on “The Tonight Show” couch with Jimmy Fallon and making a much-hyped appearance at Coachella in April, as “Messy” was peaking.

Prepping at Lollapalooza in Paris for her album’s release, Young, Shymansky and West weighed options for teasing her new single, “Dealer,” a lo-fi bedroom-soul number, after Elton John called it “the biggest smash I have heard in years” and an initial taste on social media went well.

“I spent all day tryna be sober,” Young sings on the track, about wanting to get away. “Pack my bags and tell my dealer I’ll miss him.”

On the surface, Young seemed sturdy enough to face the onslaught of responsibility approaching. But when asked directly about her sobriety, she could turn wary, taking a deep pull on her tobacco vape and whispering, nearly inaudibly, that things were simply “good.”

The album, she said, was the best document of her recovery journey. “It was dark and I’m very happy I’m growing out of it,” she said. “I want to be an advocate for people who’ve suffered, but I’m not quite in a position to go, ‘Sobriety is the way,’” she said. Not yet.

With some downtime between scheduled appearances, Young had been hoping to take about two weeks to herself before the final promo push for “Myself.” But when Fallon’s team offered a last-minute slot to perform “Dealer” on “The Tonight Show” in late July, an impromptu New York trip was added to the calendar.

It never happened. A few days after her return to London, Young relapsed, Shymansky said, and returned to treatment.

“We’ve got to be really careful,” he said in an interview in August. “No one really knows the depths of what she is dealing with.”

“Her work ethic’s amazing and her commitment to herself is amazing,” Young’s manager added, “but there’s inevitably going to be moments where she can’t keep up with both.”

With the album’s release date nearing, Shymansky gave Young the option to pause everything, including delaying a fall headlining tour of the U.K. and North America, and focus on her health. Young, he said, chose to forge ahead.

“What’s worse for Lola: huge success or no success?” Shymansky said. “I think I’ve come to the conclusion that within success, there’s some form of structure and revenue and support system.”

As she returned to the stage this month, the singer was joined behind the scenes by a sober coach, and surrounded by a team dedicated to protecting her. “The reality is, we’ve got an amazing inner circle that love and adore her,” Shymansky said. “But everyone’s on the [expletive] payroll.” The parallel to his work with Winehouse was obvious. “You can’t separate it,” he said. “It’s uncanny.”

But he encouraged Young to not only put on a good face for fans. “If you’re struggling, share it,” he told her. “Explain it to people. Give them a chance to show that we’re in a different moment in time.”

Young is working on it. Earlier this month, she moved into a new apartment — the first real spoils of her pop success so far — and celebrated on social media with her old friend Violet, popping a bottle of sparkling tea in lieu of champagne.

“I’m so excited to start a new chapter of my life,” she said, teary-eyed, in a video for her fans captioned “new beginnings.” It was one more step forward.