Olivia Dean: ‘I will headline Glastonbury one day’

I’m having the craziest week of my life!” declares soul-pop sensation Olivia Dean. She is currently backstage at the Roundhouse, where she is due to perform in a few hours. Her “crazy week” consists of what she calls a hometown “gig sandwich” – a headline show at Camden’s KOKO (which sold out in under a minute), a support slot for London rapper Loyle Carner at Wembley and tonight at the Roundhouse. It’s also her 24th birthday. Reclining on a red leather sofa, hair tied back in a messy bun and inhaling from her vocal steamer, she looks unfazed. You wouldn’t guess she was about to perform the biggest show of her life. Dean exudes such calm confidence, you feel like you could catch it.

Clearly, there is something infectious about her, or at least her music, because for tonight’s 3,000-capacity show, there are 10,000 people on the waitlist. Not only has the singer achieved early success with her storytelling songs, (sold-out tours, songs across Radio 1 and a secret set at Glastonbury), but she’s also made a name for herself in fashion, having recently become a brand ambassador for Chanel.

Music remains the priority though, especially playing live. “I love singing to people so much, it just brings me so much joy,” she smiles. Dean compares going on tour to making pancakes. “The first one is probably a bit dodgy – still tastes nice – but you haven’t really nailed it,” she laughs. “I love when stuff goes wrong – those have been my favourite shows, it’s the messiness that makes it fun.”

It’s these imperfections that have inspired her highly anticipated debut album, Messy, due on 30 June. Not that Dean needs an album; she has already amassed a cult-like fanbase, all of whom sing back every word of her candid lyrics at the Roundhouse this evening. “The thing that most people tell me is, ‘You’ve got me through a break-up’,” Dean explains when I ask what gives her such a strong affinity with fans. “Everyone has that big [split] in their life that messes you up and you kind of lose that perspective of yourself. It can feel like a really lonely experience and I guess I was just documenting that.” Later that evening, she tells the crowd, “I don’t really believe in this idea of the ‘other half’. You’re a whole person and you don’t need somebody else to complete you.”

Her 12-track record navigates falling out of love and back into it, with comforting, conversational lyrics all articulated in the warm, glowy tones of her full-bodied voice. Tracks directly address their subjects with frank honesty in a nod to her musical idols: Amy Winehouse, Lauryn Hill and Carole King. While the album features the relatable relationship ruminations her fans have come to expect, (you’ll recognise 2020 break-up anthem “The Hardest Part” and the newer and seductive “Danger”), elsewhere Dean braves introspection.

She explores identity in “Carmen”, which was named after her grandmother, whom Messy is dedicated to. “You transplanted a family tree, and a part of it grew into me,” Dean sings, referencing her grandmother’s move to London from Guyana as part of the Windrush generation. “I just feel so grateful to her for being so brave, because it’s enabled me to live my dream,” says Dean. She recalls visiting the Life Between Islands exhibition at the Tate Modern, which showcased Caribbean-British art. The work made her feel seen and connected to herself. “I feel so British and so East London – but I also feel that there’s this other thing that’s kind of missing,” she says. “The exhibition was just crazy to me. It was celebrating the beauty, crossover and the imperfections.” And so Dean arrived at the album’s title Messy, which ended up guiding her attitude towards songwriting this time around. “There’s no rules,” she says.

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Dean has routinely come up against expectations in the industry – expectations of what her music should sound like because of what she looks like. On the album’s otherworldly opening track “UFO”, Dean decided to explore an Imogen Heap sound. Yet frustratingly, she discovered the song had been added to an R&B playlist. “In what world? What rhythm and blues are you hearing? If I was white, that would just never happen,” she says. “Sometimes with the way that I look, I feel like, is my music supposed to be urban or am I supposed to make a certain kind of thing?” With two fingers up to those stereotypes, Dean simply writes what she feels. “I made Messy quite selfishly, to be honest,” she admits. “I was just like, ‘This is what I would want to listen to’.”

Dean has insecurities like the rest of us, only she navigates hers through songwriting. “I’m not as strong as I appear/ I’m way more anxious than I seem,” she sings quietly on the tender piano ballad “Everybody’s Crazy”. “I was quite nervous about that one because it’s very exposed,” she tells me. The album’s title track came to her last – and while writing it, Dean realised that the song was for herself. “I needed to write a song that says it’s okay that you’re a bit of a mess.” Perhaps it’s this commitment to vulnerability that makes her music so appealing: the fearlessness of fear itself. “I wanted to hint towards saying that feeling insecure is fine. Especially in men,” she adds, “It’s kind of sexy. Tell me you feel insecure if you do, I’ll respect you so much more. We’re all just anxious puppies pretending that we’re not anxious puppies”.

Later that evening, as her silhouetted figure skips onto the Sixties-inspired set with a happy-go-lucky wave, Dean looks entirely at home. How does she navigate such intense experiences with so many eyes on her? “Fake it till you make it!” she laughs when I ask her backstage. “That [negative] voice doesn’t exist in my head,” she says. “I just have a pure sense of, ‘I can do it’.” That ambition extends to Glastonbury, where she predicts she’ll one day headline the Pyramid Stage. “I’m manifesting it – so quote me,” she smiles. “That’s what’s gonna happen!”

‘Messy’ is out on 30 June via EMI