The art of Olivia Dean

‘It’s normally not my vibe to be faceless, but I look a mess, if I’m honest,” laughs Olivia Dean, apologetically channelling the title of her debut album as she speaks from her home in south London.

The singer-songwriter, who rocketed into the spotlight two years ago off the back of 2023’s standout debut album release Messy, is currently resting up and nursing a slightly sore throat following an “unbelievable” run of dates opening for Sam Fender at stadiums in London and Newcastle, and later on the day we speak, she will give a sold-out O2 Shepherd’s Bush an early taster of her upcoming second album The Art of Loving ahead of its release on 26 September.

“I love playing shows so much,” she enthuses, a reassuring statement from someone who will play no less than four shows at London’s O2 Arena next spring. “It’s the thing that makes me feel most useful in my life, and it’s something that I really love to do. I don’t really get nervous. I just get intensely excited. It’s all about being with people. While I love to sing personally, for myself, I find shows are the closest thing to this… it sounds kind of cliche, but… spirituality. I just feel it’s such a powerful thing.”

Touring Messy, she adds, has led to all manner of memorable encounters and connections. “I did a show once where there was a guy in the front couple of rows, and I was singing [‘Carmen’] and he held up his phone, with some text on it. It said something like, ‘You make me feel comfortable to be mixed-race.’ I was like, ‘Oh my God, stop it, you’re gonna make me burst into tears,’” she says. “It was almost a private moment between me and him. It was brief, and it made me feel really seen. That was really beautiful for me.”

Pulling from a rich tapestry of genres — from Memphis soul and Motown to gorgeously brassy retro-pop made glossy and new — Dean’s debut Messy was defined above everything else by its vivid and singular lyrical voice. On acoustic opener ‘UFO’, Dean wittily laid the groundwork for a deeply personal record centred on “me and my sexy problems”. With the candid introspection and a touch of sharp observational humour that set her apart from the rest of the pack, she proceeded to dissect faltering love stories, the solace of sisterhood, and the story of her grandmother Carmen, who boarded a plane for the very first time and travelled to the UK as part of the Windrush generation. “Carved your initials in this island,” Dean sang on ‘Carmen’, a song peppered with warm-toned steel drums, “but the Weetabix don’t taste the same.” 

The album bagged a well-earned Mercury Prize nomination, three BRIT nods, and took her all the way to Glastonbury’s Pyramid Stage last year. Though Dean says she’s never felt particularly focused on award-based accolades, she has always had “tunnel vision” when it comes to Worthy Farm. For that performance, her first time playing the festival, Dean wore a custom look with a picture of Carmen on the front.

“I’m very close with my granny,” Dean explains. “She was very present when I was growing up, and at one point, we were roomies — we shared a bedroom. When I was writing [Messy], she wasn’t doing so well, and we were spending a lot of time together, and I was asking her lots of questions about her life. She was telling me about coming to this country when she was 18. I thought, ‘Oh gosh, I don’t know if I could have done that: arriving somewhere and just being like, ‘OK, let’s find a job, and find somewhere to live.’ She had four kids by the time she was my age, which is crazy. She made a life for herself with the foresight that she wanted the life of her children, and their children, to be a better one. I thought, ‘This is a story that needs to be told and celebrated.’ Having her photo on my chest was a way of allowing her to be celebrated that day.”

Playing to a packed crowd, a near-permanent grin plastered across her face for the entire set, it was clear that Dean had something truly special, but Messy stopped head-scratchingly short of turning her into an overnight star. 

That looks set to change, though, with that album’s successor, The Art of Loving, as well as a potentially career-shifting support slot opening for Sabrina Carpenter. Dean supported the star at BST Hyde Park in early July, and will do the same at New York’s mega-venue Madison Square Garden in the autumn. Though Dean is conscious that these shows in particular are a big deal, having previously elevated Rachel Chinouriri, Beabadoobee, Clairo and Amber Mark to new levels of global recognition, she is determined to focus on having a “good time”.

“I’m trying not to overthink it, or what it means, or anything like that,” she insists. One of the Madison Square Garden shows, Dean points out, takes place on Halloween. “So I get to dress up!” she exclaims. While there hasn’t been much time so far to plot costumes — “I’ve got more things to think about before I get there,” she rightly points out — Dean is a fan of the “silliness” of the spooky season. “One time, me and my friends went on a night out dressed as monks,” she offers. Possible inspiration for Madison Square Gardens? “I’m not going to come out as a monk,” she deadpans, before bursting into laughter. 

Olivia Dean grew up in Highams Park, a quiet, leafy suburb teetering on the outer edges of the capital, and right on the cusp of Essex. As a kid, she threw herself into everything from karate to musical theatre with varying levels of success: “I didn’t get very far,” she says, of the former. “Please do not quote me as saying I’m a black belt in karate.” Eventually, her mum Christine Dean (a former deputy leader of the now-defunct Women’s Equality Party) intervened. “She was like, ‘Pack it in, babe, choose a hobby — you’re doing too much,’” Dean laughs. 

It was music, and the inherent sense of storytelling and drama in musical theatre, that immediately won out. Though she had always felt “a little bit like the odd one out” growing up, getting a place at BRIT School opened up a whole new world, and introduced Dean to like-minded mates in the process, some of whom she still works with today. As a sidenote, it was also one hell of a commute from Waltham Forest to Croydon. “An hour and 45,” she groans. “I would leave, and it would still be pretty dark in the winter, and dark again when I came back — it was quite a commitment.” 

While she was studying there, her teacher Mr Doherty showed a 17-year-old Dean live footage of Paul Simon performing ‘Diamonds on the Soles of Her Shoes’ and “it just sparked something in me. I loved the coming together of the quite traditional singer-songwriter thing that Paul Simon does so well, with this South African music, and the players, and the brass, and I just remember thinking: ‘Oh, I’d love to do that. How could I do that?’ For want of a better phrase, it was a kick up the arse.”

Shortly after this, upon graduating, Dean met her manager, who was also working with Rudimental, and when the chance to join the group on the road as a backing singer arose, she went for it. “What were the chances: you get the opportunity to play in front of those big crowds, but it’s not about you — you can learn and take that feeling in, without the pressure,” she remembers. 

“That was an invaluable experience for me, but it also definitely inspired me to go: ‘OK, could I do this myself? I think I’ve got some stuff that I’d like to say…’ I’m a real observer, I think, and I like to learn, and then apply,” she says, “without sounding too clinical about it.”

A similarly thoughtful approach has also shaped The Art of Loving. Following the huge success of Messy, Dean was feeling daunted by the idea of diving into its follow-up. “I had developed a bit of studio anxiety, I suppose, and was putting a lot of pressure on myself,” she explains. “I realised that all this time that I’ve been making music, I’ve never had my own studio. I’ve always been coming into other people’s spaces and trying to justify myself. And so I thought that I’d love to build my own space and create within it.”

Though Dean spent a couple of weeks working on the record in LA, and also recorded at New York’s Electric Lady Studios, much of it was made in London, where she decided to take a much more homely approach this time around. After converting an east London house into her own studio, she moved in, along with her piano from home, and lived there pretty much full-time throughout the creation of the album, which is produced by Zach Nahome, and features Max Wolfgang, Bastian Langebæk and Tobias Jesso Jr. as collaborators.

“I brought photos from my house, and I slept there. I would have friends round, outside of studio time, and I had parties there, so it was this real, living, breathing space. I was really deep in it, and maybe sometimes too deep in it,” she laughs. “Sometimes I was like, ‘Maybe I need to go home-home this weekend, and then listen again with fresh ears.’” 

The initial title and overarching theme for the album came to Dean last year, after she saw an exhibition by the American visual artist Mickalene Thomas — known for her brightly patterned, rhinestone-peppered collages of African-American women — at The Broad in LA. “It’s in response to bell hooks’ [book] All About Love, which I’m a huge fan of. There’s this passage in the book about the craft of loving one’s own life, and I thought, ‘I think I’m gonna call this album The Art of Loving.’”

“Love is something I have always been interested in,” she continues. “For some reason, it’s seen as this mystical, untouchable thing that we’re all supposed to just have a go at and figure out. In All About Love, bell hooks is like, imagine if we had a class in primary school that was, like, emotional studies? So that we could teach each other a bit of etiquette, and how to fill each other with care? I just wanted to do a deep-dive on love, to understand why I love the way that I do, and how I love other people.”

Filled with warmth and joy, The Art of Loving is a continuation of Messy’s eclectic sound — and also shares the blurred aesthetic of her debut’s cover art. “It’s representative of imperfection,” she says. “Some of the stuff I’m speaking about isn’t fact, or always the truth — it’s just my truth. I kind of want people to hear their own truth,” she says. “So I don’t need you to have a big fat picture of my face when you’re listening to it!”

Far from treading familiar pathways, Dean frequently finds new inroads into a weighty and much-explored subject. The funk-inspired ‘Lady Lady’ for instance — laden with clavinet melodies that recall the music of Stevie Wonder — is addressed to a mystical higher being, influenced in part by the Norwegian-American artist Okay Kaya’s song ‘Mother Nature’s Bitch’. 

“Last year, I moved house three times against my will. My whole building got evicted, and then there were some problems with another flat I was living in, and it was super disruptive.” Dean couldn’t stop thinking about the idea that a higher force of some kind was trying to tell her something in her life needed to shift. “It’s about the universe, Mother Nature, or God, if you will, and the plan that she has for you.” 

As well as the sorry state of the London rental market, perhaps? “Yes,” she laughs. “This one goes out to my landlord.”

Along with the Michael Jackson and Tears for Fears-influenced ‘Man I Need’, the vaguely bossanova-flavoured ‘So Easy to Fall in Love’ is another intriguing standout — despite being a love song, the person it’s addressed to is barely visible, and many of its lyrics celebrate its narrator instead. “I’m the perfect mix of Saturday night and the rest of your life,” she sings with a wink. 

“Sometimes, when we get into relationships with people, we focus a lot on — as we should — how brilliant they are. But I think it’s important to remember that you’re also excellent, and you bring a lot to the table. Why shouldn’t somebody want to fall in love with you? You’re amazing! They would be lucky to, and not in a narcissistic way. I love that song. I think it’s really funny. It comes from a pure place, rather than being like, ‘I’m the best person in the world.’ You know? It’s saying, ‘Oh, I think I’m quite great.’ Why not?

“I would never sit here and proclaim to be like the Oracle, or the wise owl of love,” Dean laughs, “and I’m definitely still figuring it out for myself, but I think the base foundation of love — and truly being able to love someone else — is understanding. Really trying to see someone, also allowing them to change. I think that you have to turn up and love the person that’s there every day.

“Above everything else, I just hope that people enjoy it,” Dean concludes of the album, “and ultimately have fun with it. I feel this album is both intensely serious,” she says, “but also quite light.”

Taken from the August/September issue of Rolling Stone UK, out now. Subscribe to the magazine here.