
From life as a punk to pop manifestos, musical polymath Jessica Winter walks Jasleen Dhindsa through the pivotal songs that have shaped her artistry
The intricacies of identity define Jessica Winter’s life.
Which is understandable, given that the Portsmouth raised artist has worn many hats throughout her career as a musician. Punk bands in her early teens provided the basis of her group Pregoblin, formed with Fat White Family’s Alex Sebley, and since disbanding the project, Winter has released a slew of singles and EPs since 2019, supporting fellow electro pop trendsetters Jake Shears and Rebecca Black on tour, through her own transcendent floor filler pop earworms, tinged with nostalgic production and that unmistakable extraterrestrial vocal.
Whilst her new album, aptly titled My First Album, is a culmination of all that has come before, rather than closing the door, it leaves it flung wide open, both honouring her past and exploring all that is still unknown.
Through bursts of moody guitars and 90s alternative sensibilities (particularly on the call to action bursts of punk on "All I Ever Wanted" and "Got Something Good"), you get transported to what enamoured Winter as a teen, but importantly what inspires her to this day through limitless and dream-state electronic music.
When naming the album, Winter took a retrospective look at her life and all that inspired her, whether that be real life experiences or the music she was listening to, “there was a real innocence in making this album because it was always going back to where I came from,” she tells me. “I'm releasing my first album much later than most pop artists would. I've had a whole lifetime of music, I've written over a hundred songs that are released, so I just thought people need to know it is my first album [although] I have been around the block. With the way I've named things in general I'm very matter of fact, I don't like dressing it up in something it's not, or trying to over egg the pudding!”
Speaking further on her journey to the album, Winter says she’s transformed in how she looks and behaves in life, “it makes you zone in on what it is you want out of life. What's important and authentic, and your identity comes into focus massively. Especially as a woman and how you want to portray yourself.”
“When it comes to writing the music, that is a voice all on its own that comes through from wherever it comes from, like a deep catharsis spiritual moment when you really have something to say. Sometimes it could be very silly, but it means something at the time and it's wherever you're at in your life.”
Finding her place is something Winter has navigated throughout her life, and her debut album has punctuated this feeling: “when it comes to actually putting out the album and how to do that in the current climate we're at, being older and where you sit with that in this TikTok age, with all this new speak, it’s definitely pulled loads of things into focus and where you fit and whether you feel like you fit.”

She continues, “[One of the] main issues that I've had is that I never really give a shit about the visuals or imagery at all, because I just love [the] music. I love playing piano and that's all I care about, I could wear a cardboard box and it's fine. When I was like sixteen I was dressing as a goth, then I was a psychedelic hippie. I liked so many different guises. Now, I realised that I was just this person who really didn't know who she was. I love how music has helped me be all these different people that I've wanted to be, and I still will be I'm sure. I feel like this is more defining through the EPs and up until now… I am becoming and feeling good within who I am and not having to be something I'm not.”
My First Album does feel as though Winter has confidently arrived in a place that is solely her own, sonically and visually. The aesthetics that accompany her music are strong and unmissable, whether that be slick social media posts or her artistic music videos, it’s nailed, partly inspired by her mum’s career as an 80s glamour model (“I just think it looks so good. I've always been proud of what she did” she says), but lies somewhere between the stylish sharp high concept lines of The Matrix, NYC yuppie and New Romantic.
“The way they shoot glamour models in the 80s was so high production and I love the structured themes,” Winter tells me, “so I've always had this weird identity crisis, where I've had a really ultra feminine mum who's glamorous, wears a tiny bikini and is really tanned [with] this perfect body. But then I've also been this man who loves wearing suits. When I put on my suit I've got that power, and then when I wear my little bra, gloves and high heels I'm ultra femme. I like presenting both worlds.”
The breadth of all that inspires Winter is reflected in her expansive song selection.
"Sat In Your Lap" by Kate Bush
JESSICA WINTER: I lived with my uncle as soon as I left Portsmouth for ten years. I left my home at about sixteen, so he's kind of like my gay dad. He raised me on Kate Bush, he would also drop round Tori Amos CDs.
He’s definitely been a big influence, I can’t remember when I actually discovered her because I was very young, but I love the sound of obsession and spiritual unrest in that song. It has that theatrical mania, which I feel as well. I think it was the first time I heard someone make being lost feel like a form of power. Which is owning who you are, and being okay with not knowing really who you are.
BEST FIT: Do you think that's something thematically that you explore in your new album?
Yes, I think that's going right now, the pressure's on you and you have to be this person and this pop star, and all the songs that are going to come out of that are around, 'What am I? Am I enough? I want this, do I want this? What do I want?' All of these questions which all go with come with coming of age.
"Faceshopping" by SOPHIE
There's obviously pioneering production, and I love the lyric ‘I'm real when I shop my face’. Again, it's about identity and beauty, and how it can be so feminine and it's coming from somebody who was not born with the right genitals.
Are you an original SOPHIE fan?
Yeah. I can't remember what that was, like, ten years ago? I remember that feeling of being excited, like when I first found heavy metal when I was fourteen, I [felt] this is me, and I had the same feeling when I heard this music and I got obsessed.
"Closer" by Nine Inch Nails
I just love it. It's so naughty! It's probably the filthiest song ever made. But it’s also really tender. I love their juxtaposition in the production, how soft the vocals are, you can hear everything in the vocal with such distorted heavy backing. And then it flips and it can be really painful and you can hear the voice hurting. I love that dichotomy, I love two worlds combining in music.
You were talking about how you were really into heavy music when you were younger. Talk to me about how you came across that, would you describe yourself as an emo?
I was really anti-emo because I came from punk music. I was into the big punk movement in Portsmouth, everyone’s uncle or someone they know is in a punk band. I loved the fashion and the anger. I was really angry as a teenager, and loved the feeling of going out and being naughty. I think everyone does that, don't they?
I used to listen to emo music but I would never admit it because it wasn't cool. I wasn't allowed to because I was a punk. I bought this twenty year old car recently, and it has a CD player in it. So luckily I kept some CDs I haven’t seen since 2000 and whatever, and there’s so many emo songs in there.
Are they mixtapes that you've made or actual albums?
Oh yeah, downloaded from Limewire!
"When I Grow Up" by Fever Ray
I think I resonate with this because sometimes when I hear her I’m like, 'Oh is that me?' I don't sound like other people, but then when I hear Fever Ray I'm like, 'Oh she has a weird voice', and it made me feel like it's okay to have a voice that doesn't necessarily fit what everyone else is doing.
I love the feeling when you hear a Fever Ray track, it's more about their whole aesthetic. It’s eerie and soft, and it's like someone's dancing alone. It sounds like someone's got some childhood trauma in there.
"Waterfalls" by Paul McCartney
This is ultra songwriting. It’s such a beautiful, beautiful song, and Paul McCartney is my choice of Beatle, even though people think I look like John Lennon, and I do love John Lennon's solo album John Lennon/Plastic Ono Band, but Paul McCartney is just non-stop with the songs.
I love how honest he is, this song specifically feels like a lullaby almost and makes me feel like a child when I listen to it.
"Fuck the Pain Away" by Peaches
I got to play with her in Liverpool, and hang out with her in the dressing room and get ready with her and everyone in there.
When was that show?
That was two years ago. There was this huge inflatable penis. Very theatrical.
I just love the world that she's made, and she's just a force for feminism and queerness. She’s such a badass, and she's so strong and terrifying. You don't know whether she's going to hug you or hit you, but she's just brilliant and really kind. I think there should be more people revving her up.
"Rid of Me" by PJ Harvey
I think it's one of the most terrifying love songs ever made.
It's so intense and it's one-of-a-kind which is really hard to do. She's a voice where you can be a woman and be angry at the same time. She doesn't necessarily fit a box specifically, and you can't really pigeonhole who she is, which I really like.
I love her style, and her makeup. It's iconic.
"Walking In The Rain" by Grace Jones
I'm quite obsessed with pop and to see how far I can push it within a structure, and it's only songs like this which can inspire you to do weird things within that. Without these songs, you wouldn't have great pop music as well.
I love the lyric feeling like a woman, looking like a man. I really resonate with that all the time. She just represents alien sexy cool, and controlled. That's the thing, this song goes on and goes to different places, but it all feels very controlled at the same time.
She’s so good at exploring all these elements, but also having a distinct style that needs no explanation
Yes, if she was to say ‘this needs to go over here’, and you think that would be crazy, but she knows what she’s doing, so we must!
"Drowned World / Substitute For Love" by Madonna
I've always been inspired by Madonna, and her energy and confidence. It's weird, you know, we’ve got Kate Bush, who's revered because she writes her songs but Madonna doesn't really get that.
She gets it in a different way of just being this person, obviously a huge superstar, but I don't think people really talk about the fact that she is really an amazing writer as well. Do they? Because I never hear that. They talk about her style and her voice.
I like this specific song because she says, 'I've changed my mind', and it's looking at one thing versus another. Like fame versus a feeling, or noise versus silence. The song captures something, after she's had something, which I always think about. Like when you've had a really great moment, and then you come down from that and how you feel, and what you wrestle with when that happens. It's one of her most human moments for sure.
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