Live, laugh, vom: the weird world of Jessica Winter

It’s Friday night in Soho and Jessica Winter is wearing thigh-high royal blue boots and spewing all over the pavement. Holding her hair back is Rebecca Black, the pop musician best known for the 2011 viral track “Friday” (and the hyperpop version released ten years later). The two have just played a packed-out show at London’s gay club Heaven, with Winter as the support act. It had gone well. The girls and gays had been screaming and fighting each other, phones aloft, to catch Black’s rendition of “A Thousand Miles” by Vanessa Carlton. And then Winter and Black had gone out afterwards, cheersing with tequilas, which had inadvertently led to the vomming (or so she relays to me later).

Black may have had audience members screaming “Mother!” that night, but for any music nerds in the crowd, it would have surely been Jessica Winter who made their heads snap to attention. With a look sitting somewhere between a gothic AG Cook and a 1980s Isabelle Adjani, she’s hard to ignore. But it’s her music that’ll make your ears prick. Think squelchy Max Martin-like pop hooks with an operatic, Kate Bush vocal. Or Róisín Murphy beats with a Kylie twist. Or a musical theatre production, directed by Danny L Harle, for the euro club. She’s hard to describe in the way that Rina Sawayama was hard to describe, at first. She makes weird, moreish pop music about being sad and in love, with lyrics like “You’re something like a knife / splitting me up in the night.”

A week after the Heaven show I’m sat with Winter in an east London mezcal bar, sipping on slime green jalapeño margaritas (“Just one, after last time,” she says). She’s arrived with a selection of baked goods wrapped in paper, including iced buns and slices of potato bread (“Please, have some”), having just got back from Oxfam London Fashion Week. Other than that, she’s been touring with Black around the UK and watching Sex and the City reruns in the interim, which she literally just discovered the other day (“Can you believe I’d never seen it??”). Curls tangle around her forehead, grey eyeshadow glinting beneath the bar’s coloured lights.

Winter grew up in Portsmouth, and then a tiny island beside it. If you were to zoom in on ‘Hayling Island’ on Google Maps, you’d see long stretches of flat beachland, faded pastel-coloured amusement arcades and charity shops. As a teenager, she spent her time listening to heavy metal bands like Korn and Lacuna Coil and smoking weed with boys she met at the skatepark, dreaming of an escape. Her mum was a glamour model, while her dad was a wheeler-dealer businessman who sold mobile phones. “My mum did a load of DVD [glamour modelling], although she ‘never opened her legs’, that was her rule,” Winter says. “I was so proud growing up, I had [her] pictures on the wall. I never really thought anything of it – I just thought it was really cool.”

As a kid, Winter was diagnosed with hip dysplasia – a condition in which the hip socket is misaligned – which meant that she spent much of her childhood sitting down, at a piano, in between operations. “That’s my X Factor story,” she says dryly. “I had a back brace and so [my mum] would put me onto the stool and I’d be there for ages playing piano because there was nothing else to do, other than watch telly.” The piano became her main instrument, the one she felt most at ease with, like an extension of herself. While she’s saying this, I remember her blue boots on stage at Heaven the other night and how they looked vaguely medical, like orthopaedic casts. I ask whether that was intentional; a wry fashion ode to hip dysplasia. “Yeah, yeah it was – medical fashion!”

Her big move to Brixton, London, came at 18. What followed was a decade of finding and re-finding herself musically. When she tells me about the bands and eras she went through in her twenties, it’s hard to keep up. There was the time she studied music for nine months, before dropping out when they tried to make her do vocal runs “like Beyoncé”. There were the record deals that never properly materialised. There were the years she got really into LSD and started making psychedelic dream pop after becoming obsessed with 1960s band Love and their famous third album, Forever Changes. “It changed my life. I’d done classical my whole life and I feel like 60s music is close to classical,” she remembers. “I found out about other eras as I got older. I got heavily into each decade of music every couple of years.”

If there’s one band you might know her from, though, it’s Pregoblin, a duo comprised of her and Alex Sebley, formerly of Fat White Family. Together, they made weird, beguiling DIY music that sat somewhere between psychedelic, disco and post-punk. They’ve got a couple of videos on YouTube, including this one of them riding horses across the field like two freaky cowboys. Being in Pregoblin was important, she says, because it allowed her to step more confidently into the producer chair and take control (she’s always produced her own stuff, but the men in the room so often bulldozed her). Even so, around the pandemic, chaos reigned and Pregoblin fell apart.

“Drugs always get in the way,” she says now, twirling her margarita ice with a toothpick. “Heroin is not a nice drug and so I had to step away, because it was getting a bit dark. It’s just that world that Fat White Family are in – they’re into self-sabotage. I remember us signing the dotted line that was for like, one EP and an album. The album [deal] was for like 100 grand. And I was like, ‘Please, let’s not fuck anything up until we get the album.’ We didn’t even get to the EP. We got the second or third song on the EP released, but then it was chaos [with Alex]; we were always falling out, fighting. So we didn’t even complete the fucking EP, let alone the album.” They’re friends again now, but it’s taken time. “We might even get back in the studio.”

Winter had been making her own stuff alongside everything anyway, and in 2020 she released her Sad Music EP, followed by More Sad Music in 2021. Most recently, she put out Limerence, an exuberant, paradoxical slice of pop about love, loss and relationships. In “The Love Song” she sings “When I hear you in the morning, it makes the demons go away” over a chugging guitar riff that warps and bends like a heartstring. Why is she so drawn to writing about love’s melancholy, twisted shadow? “I’ve never been very successful at it,” she says. “I do think [romantic] love is possible, it’s just taking me a bit longer. Maybe because I had such an unhealthy teaching growing up. I’ve had to relearn a lot of what healthy love looks like… I was drawn to wild, unstable characters. But I’m not ruling love out yet – don’t worry.”

Winter blames part of this feeling on the “difficult landscape” we’re in now. “Everyone is a bit lost,” she adds. “We’re ever more separated from intimacy than we think we are – it’s really hard to connect. So I just sing about these things that upset me a lot. I’m desperate for something different. If no one says how they really feel, how is anyone supposed to change?” At this point, she casually drops in the fact that she got married at 22, and that she’s currently in the process of getting divorced. It feels fairly typical of Winter – just another odd addition to what’s already been a comparatively colourful life. “I’ve been in codependent relationships, it’s been up and down, like romance in a film and then it’s terrible, traumatic. I didn’t know who I was, or what I wanted.”

Suddenly it’s 10pm and the night is closing in on us, or at least on the cusp of turning. The air outside is thin and spring-like, warmer than you’d expect for February, and we spend some time walking the streets, snapping photos in a local off-licence and hanging around the bin-studded Dalston alleyways. Winter says that after vomiting the other night she’s learned her lesson about touring: you always party at the end, never at the beginning. She won’t be doing that again. The next day, while performing in Bristol, she’d thought she was going to drop down dead, or at least vomit again. Torturous. 

So what next for Jessica Winter? She tells me that she’s supporting someone cool very soon, but it’s not confirmed yet, so I can’t reveal anything in print. Other than that, she’s working on a debut album, hopefully out before the year’s through. She doesn’t know what it’ll sound like, but she has some ideas; each song tends to unfurl itself as an individual creation, untethered to genre or the past. 

As I leave to catch the overground, I’m thinking about what Winter told me earlier, about becoming solo, and taking control of her own creativity. “I needed to have something that was mine, that was sacred,” she’d said. “I was like ‘fuck it, I can’t rely on anyone. I can only rely on myself.’ I had to take a moment to be like: who am I, what am I and who do I want to be.” Right now – from the outside at least – it looks as though she’s found out.

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