How Holiday Sidewinder Sold Used Panties To Create The Year’s Best Pop Debut

Holiday Sidewinder has dreamed of releasing her debut album since she was a child — it was written in the stars, she says.

But all dreams change, and the record that’s out this week — Forever or Whatever, a collection of bold, anthemic pop songs that might be one of the most entertaining releases of the year — is the kind of thing she never could have planned for.

“I moved to London when I was 21 with the very specific intention of writing my debut solo album,” says Sidewinder, who tours with Alex Cameron and found teenage fame as one of the members of cult Sydney act Bridezilla. “I didn’t have any instruments when I first moved and couldn’t afford them, so I only had access when I was booked into a studio session.

“Sometimes I’d have to wait months for the studio for whatever reason, and I’m terrible at computer music. So I was writing at home, hitting things on tables and putting effects on it, building harmonies. At some point I just went, ‘Fuck it, time to stop being precious.'”

Along the way, the record transformed. Originally conceived as a collection of Shangri-Las-style teen gospel pop songs called Valentine, as Sidewinder grew, so did the work. Recorded during half-day sessions while she worked at a bar, a lingerie store, and the gym that she ran with her then-boyfriend, the album quickly became a bold, metallic series of songs about love; about life; about the things that happen when you open your mind to all kinds of possibilities.

“Music has always been that for me,” Sidewinder says. “I can always rely on it to make me whole again — like a really good lifelong friend. So although this is my first album as a solo artist and reflects a really specific time in my life — hello Saturn return! — to me, it’s a chapter in one cohesive linear album that runs alongside my life. Like footprints. Or wrapping bits of material around branches as you go on your way, so you can find your way back home.”

Like Sidewinder herself, Forever or Whatever is whip smart; the kind of clear-eyed record that holds you up to a memory and then nails you there. Even the vaguest moments on the album, as when Sidewinder sings a bunch of rhyming words in lieu of a chorus on ‘Casino’, are grounded in truth. Holiday Sidewinder doesn’t lie, ever, and this is a record that trembles with the full force of someone explaining the world as they see it.

Of course, it’s also unashamedly poppy. ‘Baby Oil’, the album’s standout single, sits at the exact midpoint of workout tapes, Mills and Boon romance covers, and the abrasive honesty of Nine Inch Nails. It’s a darkly twisted thing with a shiny, polished surface, equally suited for date night or the lonely hours that come after, that early stretch of the morning when you’re left alone, sitting on your balcony, staring out into the murk.

“Pop is the only genre that you can’t be confined in,” Sidewinder says. “There are no rules. You can’t guess what’ll be embraced by the masses. [I] come from an indie background, and I was a jazz junkie for years too. But even with the promises of freedom from constraints within those genres — with improvisation and not having to have polished production or conventional song structures — it’s a smaller box you put yourself in.

“Those scenes are naturally protective of that culture because it’s their identity, and that can lead to a homogenisation that feels dampening to creativity and exploration to me.”

“Pop is the only genre that you can’t be confined in. There are no rules. You can’t guess what’ll be embraced by the masses.”

Sidewinder’s honesty extends beyond just the music, and her relationship with her fans is unlike many others in contemporary pop. Sure, Ariana Grande replies directly to her stans on Twitter, and Taylor Swift invites her most devoted followers to private listening parties at her house. But Holiday Sidewinder sold enough of her worn panties to her fanbase that she covered the cost of her album’s mastering, something that she describes as “fucking hilarious and perfect to me”.

Then there’s the time that she tried to find a boyfriend via her Instagram stories. “I posted a sad photo of a matzo ball soup my date was eating and said, ‘Looking for a new BF, send resumes, will not babysit you.’

“I was flooded with ‘applications’. It was a week-long comedy show. My favourite was this guy called Stanley Kim in Austin, Texas who sends me $50 on Venmo every now and then. He wants to be my finsub [financial submissive]. He came to a show and didn’t say hello, just sent money saying he was there and that the gays love me. Another application sent bitcoin to outbid Stanley in the FinSub department and I ended up marrying him.”

Sidewinder has been playing the music industry game for a while now, so she knows the tricks. But while some of her contemporaries seem terrified of the way that the digital sphere has upended old practices, Sidewinder isn’t concerned.

“It’s weird for me, because I’m a ‘music person’. It’s my life, my job, my passion… And yet I don’t buy music or go to shows very often,” she says. “I used to go to concerts every other night, I had an enormous vinyl and CD collection. I guess since I’ve been transient and I have had no home, never sure what country I’ll be in and no disposable income, streaming works for me.

“However the monetisation of music works out, there is no doubt in my mind about how integral music is in every aspect of our lives. Music revolves around us, and us around it, and it’s incredibly powerful. Whenever I remember that, how it’s consumed doesn’t matter. As long as you’re bringing something of value into peoples lives, the rest falls into place.”

This is Sidewinder’s attitude towards most things. It calls to mind something that author John Cheever wrote in his short story ‘Torch Song’, about a character who made no plans for the future not out of a cynical lack of care, but out of an “excess of hope.” What better way to describe Sidewinder, or her new album; this brilliant, shining thing, somehow totally out of our depressed, aimless time and completely situated to inspire those in it. A record that believes, ultimately, that fun is a good thing. And that it matters.

“I just want to please myself by creating and actualising what I see and hear in my head,” Sidewinder says. “We define our own successes. I’d like to perform a two and a half show in a stadium full of my own fans, and would love a chart hit, but that’s just a desire. There’s hard work, perseverance and talent, and then so much of it is luck, timing, zeitgeist and perhaps for some, knowing the right people.”

And anyway, till then, Sidewinder has things to keep her occupied.

“I married a mystery man on a whim, after a week, on a beach in Koh Samui eight weeks ago,” she says. “I don’t think it’s legally binding in Thailand. We’ll see. Forever or whatever?”

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Holiday Sidewinder’s debut album Forever Or Whatever is out Friday October 4 through Personal Best Records.

Joseph Earp is a staff writer at Junkee. He tweets at @Joe_O_Earp.