Somewhere in London, Jessica Winter – veteran musician, theatrical performer, and delightfully direct songwriter – is plotting her next artistic metamorphosis. “I’m at rehearsals for my new live show,” she explains. “Feeling grateful to be able to produce a bigger and bolder set than before!” The enthusiasm is palpable, and Winter has earned every ounce of it.
After years of navigating the music industry, her debut arrives bearing the wonderfully straightforward title ‘My First Album’ – a choice that playfully nods to her extensive history in music while embracing a certain childlike frankness. “That’s exactly why!” Winter explains. “As with all my previous titles, I don’t beat around the bush, ‘Sad Music’, ‘More Sad Music’, and ‘Limerence’. The title sounds innocent, a little bit of my inner child coming through as I sort of got back in touch with her while I was making the album. Even though there are nearly 100 of my songs out in the world now, it’s only fair to call this for what it is: My first album. Also, it sounds quite funny.”
That blend of earnestness and wit has become something of a Winter trademark. Growing up on two small islands off England’s south coast, she spent much of her childhood in and out of hospitals, beginning with hip surgery at age one. Music became both escape and expression, starting with a piano discovered during recovery periods. This early confluence of adversity and creativity has helped to shape her artistic journey, leading through various musical incarnations, including her teenage punk band Rotten Luck and later the art-pop outfit Pregoblin.
Winter’s approach to art and life seems to follow an internal compass that points toward authenticity rather than convention. Her creative process reflects this, capturing experiences as they occur rather than constructing carefully manicured narratives. “It was all happening in real-time,” she reflects. “It’s chaotic and very of the moment which you can hear across the album. Capturing life experiences and lessons as I go. That’s art for me.”
The road to ‘My First Album’ has been anything but straight. “It’s taken around two years to make, but some instrumental snippets have been with me for most of my life,” Winter reveals. “One song in particular has been looping around my head for around 15 years. It was cathartic to see it come to fruition.” This long gestation period has allowed the album to become something of a time capsule, preserving moments of both triumph and tribulation.
That sense of catharsis permeates the record. “I got dumped right in the middle of it all and you can really hear that on the songs!” Winter admits. “I was so happy for the first half of the album and then so unhappy for the second half. There’s hope at the end of the tunnel, though; I needed that to get to the final song, the closing piece!”
“I got dumped right in the middle of it all and you can really hear that on the songs”
The album’s emotional trajectory mirrors Winter’s own, with each track serving as a waypoint on this musical odyssey. Her collaborative approach has evolved too, informed by past experiences but not limited by them. “I think with any collaborator, I’ve had a synergy with what they represent, morally and politically, rather than the sound world they live in,” she notes, suggesting a philosophy that values integrity above all else.
Her latest single, ‘All I Ever Really Wanted’, captures this emotional turbulence with characteristic frankness. “I wrote this after making yet another boo-boo and watching in real time the consequence of that,” Winter explains. “I created the song in delusional desperation. ‘All I ever really wanted was a feeling’ is a feeble excuse for my selfish endeavours while life implodes around me.”
Winter’s creative process often seems to court chaos – sometimes unintentionally. “I don’t do anything deliberately,” she says of an unexpected visit to a Scientology church that inspired one of the album’s tracks. “I wish I never went in there, to be honest, but at least I have a song that I like out of it! I guess I have been drawn to chaos and uncomfortable situations because that’s what I learned growing up. I’m trying to unlearn that all now, so maybe my next album will be really boring and considered.”
This embrace of disorder, however, comes with newly established boundaries. While Winter has previously spoken about working primarily with women and queer collaborators, she’s quick to clarify: “Strictly speaking, this isn’t true; I usually work with female and queer-leaning people when I write and produce for others, but for my album, I have purposely worked with everyone. It’s been a beautiful process because now I don’t take any shit. It’s my record, my songs, and if anyone tries to abuse a healthy work environment, they will be shown the door!”
Her artistic vision draws from an eclectic well of influences, particularly the seemingly disparate worlds of punk and pantomime. “It’s clear to see the theatrics come through in my live show; I hope to exaggerate that even more in the new set,” she notes. “Punk is a mindset for me, always challenging me to not be too comfortable in what I’m doing and to see how far I can push something or how I can flip it on it’s head.”
This multidisciplinary approach extends beyond music alone. “I don’t really separate music from acting or dancing; it’s all-encompassing,” Winter explains. “I think I’m exploring all these paths through music itself.” Currently, she’s taking an unusual step in focusing solely on her own work: “For once in my life, I’m solely working on my own stuff. It’s been weird to only focus on one thing; my ADHD brain can’t handle it! I have plans for a musical after this, though.”
“Public perception is changing and embracing weirder, more experimental pop again”
The current state of pop seems particularly receptive to Winter’s brand of fearless experimentation. “I would love to work in pop more. I love all the pop music that’s happening right now; it’s an exciting time,” she enthuses. “Public perception is changing and embracing weirder, more experimental pop again.” With Charli and Chappell et al, it’s a shift that suggests the mainstream might finally be catching up to where Winter has been all along.
Looking ahead, her ambitions remain refreshingly grounded. “I’d like to sing my songs around the world, and I’d like to make enough money to go on a holiday!” she says. These modest goals belie the scope of her artistic vision: Winter’s creative evolution is far from complete. She’s carving out a space where theatrical excess meets emotional authenticity, punk spirit shines with pop ambition, and chaos transforms into art.
And if anyone questions her credentials, she’s got one more revelation to share: “I’m also a Dork.” In the end, aren’t we all?
Jessica Winter’s debut album ‘My First Album’ is out 11th July 2025.
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