Jessica Winter

Jessica Winter Bio Feb 2025

A conversation with Jessica Winter never quite goes in the direction you expect it to. An innocuous question about where a song came from can end up spiralling in all directions from rare animals, her deep love of trains to scientology healings.

On her first full-length studio album, Jessica Winter is not healed: but she’s getting there. “I have been around the block,” she says emphatically. Dodgy industry encounters, strained family dynamics, euphoric festival sets and fucked up relationships have all led her to this, her first album - sardonically named My First Album despite her years of graft in the music industry as a solo performer, songwriter, multiple-mac-wearer and band member. It’s a record that ping-pongs poppily through the sounds that have shaped her, a collection of vibrant, audacious songs about figuring out what’s wrong with you and finding a way to make it right.

A far from ordinary childhood spent in and out of hospital provided the breeding ground for Jessica’s imagination to grow. When she was one, she went into hospital for the first of many hip operations, treatment that continued until her hips stopped growing at 16. Recovery after each surgery was brutal, her back in a brace and her legs immobilised into a wide split. How do you entertain a two year old in that position? “It’s such an X Factor story,” she jokes, “But the only chair mum could put me in was the music stool because it had these little holes my legs could poke out.” With her tiny legs wedged into the side handles of the stool, her mum would pop her in front of the piano and let two year old Jessica noodle away.”That’s how I found the piano. That’s the start of my piano journey.”

Growing up on two small islands on the south coast of England, an often dysfunctional family life led her to find solace in the theatre and yearly pantomimes, a love affair that is retained and enacted in both the drama of her stage performance and music to this day. “When you don't enjoy your home life, you need that escape - I was obsessed with the theater, the smell, the dust, the lights, the dame... all of that was just incredible…I was living in a fantasy. I think that’s why I became an artist - I’ve created a place, like the theatre where I can give myself the time to figure it all out.”

Later into her early teens she started the first of many bands - Rotten Luck, inspired by her uncle who was in a locally famous punk band. Then, at 16, finally free of the annual hospital stays, she decided it was time to start really living. Jessica left school and moved out of home, first to local squats in Portsmouth, then to London where she lived with an uncle and music became more than an escape: it became her life.

In 2016, after years of gigging in bands and writing with other artists, Jessica met Alex Sebley and together they became Pregoblin, fusing punk sensibilities with art-pop bangers, but Jessica found herself developing her own persona as an artist. Stepping back from Pregoblin, “Jessica Winter” came into sharper focus as a blend of everything that had come before: the sharp edges of punk, the open-hearted silliness of pantomime, the tragic drama of opera, and the hooks and bounce of big-haired 80s pop, here she finally is.

Since 2019, her singles and EPs have been postcards from that journey and My First Album is a fully realised dispatch from this same pathway: a bold, questioning album, full of personality sitting somewhere on the spectrum between therapy and the dancefloor.

A year into working on the record, which was started in 2023, she began to realise much of the framework of her life, even her perceptions of good and bad and who she herself was, hinged on codependency and this is when she wrote L.O.V.E. - the first single from the album. “I used to believe that all you needed was love - you know, the Beatles vibe. And in a sense, you do, but now I look at love differently. Through music I’m untangling the strands of love and panic. When you think about all of the greatest pop songs about love, lyrics like ‘I can’t live, if living is without you’, all these classic, huge, dramatic lyrics... they’re so codependent!” She joined Co-dependents Anonymous (“the most unglamorous of all fellowships!”), a therapy group that is helping her to develop healthy, loving relationships.

My First Album was never really meant to chronicle that journey but that’s the way it’s worked out. Some songs are about a character striving for fame and success - the tongue in cheek ‘Big Star’ where she lets delusions of grandeur distract her from what’s important , followed by the unbelievably catchy stadium pop of ‘Worst Person In The World’ (“I saw the film and was like, this needs to be a song”) - and others are inspired by moments in Jessica’s own life.

Having grown up in a family of unusual, “outsider” personalities, Jess is used to throwing herself into “outsider” situations that others maybe wouldn’t. “It’s had negatives and positives to it,” she says of this openness, sometimes leading her into some harmful environments. For example, she mentions with trademark casualness, “I went into a Scientology church in LA for two days straight...”

In classic Jessica Winter style, she popped in, spent two days being grilled about her deepest traumas and darkest secrets, then took what she needed from the experience and headed straight to the studio. What came out was ‘I See The Robin’, a song that stands out on the album as a real vibe shift: a psychedelia-inflected reflection, a quiet moment of observance, a paeon to grief. “I think you can hear that it’s a bit of a psychotic moment. It’s about spirituality, and when you’ve lost someone thinking that they’re there still: it’s kind of hand-in-hand. But yeah, I wouldn’t recommend going into the Church twice. No.”

By the end of the record, the love songs are no longer to perfect partners that she can’t live without, they are love songs to herself. “To Know Her” features church bells pealing (“That’s me marrying myself”) and the line, “I can make my own idea of me”, echoing that feeling that until you are fully on board with yourself, it’s almost impossible to have a relationship with someone else that doesn’t end in disaster.

“Make sure that you’re everything you need on your own before you strive for anything - that should be the priority before anything else. Do you love yourself? And if you don't, then you're just gonna have chaos - which I have had throughout my life.” My First Album is about this arrival at a new selfhood. Breaking co-dependencies and giving herself the right to inhabit herself more fully, not just by wearing her own name, but by pushing past perceptions and ideas that have hemmed her whole life as a female - both in the industry and in the wider world - the idea that she has to explain and reduce herself in order to “make sense”.

Those decisions, based on love for herself, are starting to colour everything in Jessica’s life. She rarely works with straight men - only women and queer people - after years of abuse and negative experiences that stifled her growth and well-being. The stories are depressingly familiar; studio sessions treated like dates, “research trips” that end in harassment, even a manager pressuring her to do porn.

The music of My First Album is all the better for it: there are shades of Kylie Minogue and the glitter of 80s Madonna, there’s the flamboyance of Prince and Queen, there’s energy and occasional snarl of punk and the dreamy arched-eyebrow of psychedelia. Jessica’s live performances have developed into something like panto-meets-burlesque, inspired in part by her mum’s career as a glamour model in the 1980s. Her pop persona is a melting pot of everything she’s been and everything she’s come from: and now it’s also everything she’s striving to be.

“I think the album shows that there is hope,” she says. “It’s celebrating love and celebrating a woman's journey trying to discover herself... and also having fun doing it.” In a world where maximalist pop is back and therapy memes rule supreme, My First Album is the perfect soundtrack.