An Interview with Alex Winston

Going from major label to indie, reading The Secret, and releasing Bingo!, her first album in 12 years.

Hello and welcome to ZERO CRED, the only email newsletter about music in the world. Sign up to get it sent right to you.

There is no chapter in my book SELLOUT about my friend Alex Winston but there probably could have been. The Detroit native wields enough major label horror stories to fill her own book. At 22, she got signed to Island Records UK and released her debut album, 2012’s wildly unique King Con, a bombastic and confident burst of weirdo pop that was a bit ahead of its time. Prime example: She wrote a song about being in love with an Elvis portrait called “Velvet Elvis” a full six years before Kacey Musgraves did the exact same. (Though to be fair, “Weird” Al did it more than a decade before either of them.) 

But shortly after signing with Island, Winston and King Con got swept into another label, V2, and largely got lost in the shuffle. Without tour support or a marketing push, King Con did not get the chance it deserved. She then signed with the Lyor Cohen-founded 300 Entertainment and made a follow-up record in 2015 which ultimately got shelved before she was dropped. After these frustrating major label experiences, Winston took a long break to regroup and reimagine her music career. But the more time that went by, the harder it got to step back into the ring. There were the practical challenges of how to scale down her big-budget style to a more manageable level, but also the emotional challenges of overcoming years of crushing disappointments. 

I have always promised Winston that when she was ready to release a new album I would gladly interview her about it. She has sent me stray songs over the years, but none of them ever led to a larger work. It was only about two years ago that it seemed like she was seriously focused on making a full record. And now, at long last, she has finally released her long awaited second album, Bingo!, independently, and celebrated with a release party last week in downtown Los Angeles. We recently talked about going 12 years between albums, detaching from expectations, and how her major-to-indie career has felt like, as she puts it, “reverse Benjamin Button.”

How did it feel to play at your release party last week and celebrate your first album in over a decade?

Alex Winston: I felt really proud and I actually felt like celebrating, which is not an experience I've felt before when releasing music. It just felt very different, I think because I did it independently and there wasn't this external pressure. I used to constantly feel like I was not doing enough or other people were disappointed with what was happening. I know how challenging this was for me in a lot of different ways, and I did it. I'm proud of the fact that I did it. And it just feels really good to put music out again and I'm the only one I have to answer to.

How did you get signed to Island at just 22? 

I was writing demos in my dad's basement in Detroit. This was after being in a local band. I wanted to start writing my own music. A Detroit friend of mine, Aaron, who had just moved to New York, was like, “Just come visit and I'll introduce you to everyone I know.” He was in college at the time and he happened to go to school with a producer who turned out to be my first collaborator in New York. And he was like, “I love your demos!” And that was the first time anyone had liked anything I had written and produced myself back in Michigan. It was “Choice Notes,” actually. He was like, “This is so cool and fun. I want to work with you.” And I was just like, “I think I'm going to move to New York.” Like, in that moment, I was just like, “Fuck it. What do I have to lose?” And so we worked together and released a few EPs out of his studio in Chinatown called Heavy Rock. He was in a band called The Knocks, and I started working with their manager. And then things went quite quickly—probably too quickly—after that. I played CMJ and different showcases  and ended up signing to Island. I think, at the time, they were just a bit more accepting of left-of-center, eccentric pop.

What year was this? 

I'd say 2011, maybe. I know I moved to New York in 2010, and it was shortly after that. 

OK, so 2011, that was sort of the last gasp of traditional record label deals and traditional record label money. I remember you got a pretty decent budget for King Con. 

Yeah, that was a pretty good record deal and it was in pounds, so I was making a little extra there. And a big publishing deal, too. It was a big budget, but I was an idiot and I didn't understand at the time, because I was a child, how to manage said budget. I wanted this big band with my backup singers who were my best girlfriends. It added up quite quickly.

Sure. But I do think that record holds up really well. And I doubt you’ll take credit for this, but I do feel like it was a bit ahead of its time. I hear a lot of off-kilter pop now and I do feel like you were ahead of the curve there.

Well, I didn't know what I was doing, and I think that helped in a weird way. I just did what I wanted to do, and it came out that way. I think it was an uncalculated record, and it was just what I was consuming, which was a lot of weird documentaries and a lot of voyeuristic things. There was a lot about other people and the human condition, and I think I have always been fascinated by that, and then I put it to some pop music. So, I don't know if I was ahead of my time. I was just uninhibited, in a way, and didn't give a shit, because I didn't know what I was expecting. 

So then what happened when King Con came out? Did Island help you distribute it in America? 

No. So, right before King Con came out, I was downstreamed to another label. It was called V2 / Coop. I think they didn't know what to do with me. I think that has been the thing that has followed me around throughout my whole career, at least with labels and stuff. They just don't know where to fit me. And to be fair, I think it was a very American record, in a lot of ways, and the themes and even just what I was interested and influenced by… Like, I did a live Townes Van Zandt cover that was supposed to be the last song on that record, but it didn't make it on. I just think I wasn't what they were expecting to sign. So they didn't fully drop me, they downstreamed me, and then that label ended up kind of collapsing. The record came out, but there was no budget to promote it. No one even knew it came out except you. [Laughs] It just kind of all collapsed on itself, and then I got dropped.

Were you locked into a contract with them?

No. They kept all my masters and I have to recoup that if I want them back, which, who knows if I ever will. Hopefully, one day I'll recoup that record deal! But no, I was able to walk away, just not with any of the ownership of the music, unfortunately. And it sucked because I was supposed to go on tour. I had just gotten a supporting slot, a month-and-a-half-long tour that was supposed to promote the record, but they weren't going to fund it, so I couldn't afford to go. I was just disappointed because I had worked really hard on the record and I didn't feel like I could support it in the way that I wanted to. 

You did get some cool music videos out of it though.

Oh yeah. [Douglas Hart] from the Jesus and Mary Jane shot the “Velvet Elvis” one. That was crazy. That was a whole studio budget that was nuts. And the “Sister Wife” one, they let me do that video, which was also an insane music video.

Which is based on the movie House.

Yeah! Which a lot of people don't know, that it’s based off of a Japanese horror film. But I did get to do a lot of stuff. I got to tour before the record came out. I got to experience so many amazing things. I think it was just when the record came out, it all started to unravel.

How did that affect your relationship with music going forward?

Well, now, after years of therapy [laughs], I realize I was scared to put music out again because I was afraid of feeling that disappointment again. And when my second record didn't come out, I think somewhere deep inside, I was relieved, because that first record and what happened after that, feeling really misunderstood and really invisible, made it really hard for me to want to put myself out there. I don't think my timing's ever been right, and maybe, like you said, I was a little ahead of my time for what was happening in pop music. I just felt misunderstood and like I failed, and it was disappointing and, frankly, heartbreaking. I think that's why it has really taken me this long to get back out there, because I had to work through a lot of that.

Was the second record supposed to be released with V2 as well?

No, that was with 300. I put out one song independently called “101 Vultures” about my experience at Island. Then you wrote a piece on me, and an A&R from 300 saw that piece, and they signed me. So, it's funny, you kind of contributed to it.

Sorry!

[Laughs] No, no, in a good way.

So how was your experience with 300?

At that point, I had a weird complex from the first time it failed, so I was going to try to do a bigger, more straightforward pop thing. I was trying to prove a lot, which ended up just getting in the way because, frankly, you could tell I was trying to do something. Not that the songs weren’t good. There are a few really good songs on there that are very special to me. A couple of them came out on EPs, like “Down Low” and “The Day I Died.” But with King Con, it just was what it was. This time, I felt like, “I want people to know I'm a good writer. I want to be seen. I want to be taken seriously.” It was a lot of pressure on myself and maybe just not who I am. So, I wouldn't say it was all on [the label], but I think, once again, they maybe expected something different out of me than what I delivered. 

I will say, I spent time being angry and acting like a little victim after getting dropped from that one, but really, I totally understand it. It sucks. My A&R from 300, who I actually reconnected with recently and helped me on this new record, he had a job to do. I think sometimes we get really mad at these people at labels, but he was a really good guy who really did want to support me. I just think there was a lot of pressure to produce a hit, and I didn't do that for them and they'd spent a lot of money. I think at some point they just decided to cut their losses, which happens a lot.

So, you have these back-to-back frustrating experiences with bigger labels. What then? Did you want to make another record right away?

Well, when I got dropped was right when I got [Lyme disease]. So, realistically, I wouldn't have been able to tour or do anything with that record anyway. But I think I was relieved at the time because it just felt like it was getting too close again, and I think I was scared to put it out in the world. After that, I was just focused on my health for a while and that's why I moved [to Los Angeles]. So I kind of just licked my wounds and didn't do anything for a few years. I was puttering around and figuring out what I wanted to do. I released a few singles, I was writing but not really finishing a lot of things, really indecisive and kind of scared to get back out there. I think I spent a long time hiding and almost making myself smaller.

You are unlike a lot of my friends because you did not come from a punk background where everybody expects you to just make things for no money. You made big albums and put on big shows that cost money. I feel like it took you a while to come around to the idea that you could do this on your own. I actually remember you and I went to a Chris Farren show and he played by himself. I remember looking over at you and it seemed like you were having an a-ha moment, realizing you could do things on a smaller scale. Am I wrong on that? 

No, you’re right. It was amazing. It was just about him and he puts on such an amazing show and was so creative with the lighting, the loops, and everything. It felt like such a big show yet it was just him. And it really got me inspired, but I almost think, up until now, I needed a lot of padding around me because maybe I wasn't so secure to think that I could do it myself. So, I think my big band—even though I loved the way it sounded and it was important for me sonically to have those things and to make it sound lush and big—I think I didn't have the confidence just to stand on my own. And when I saw him perform that way, I just thought it was so cool and so unique and just as impactful as having, like, seven people up there.

With [Bingo!], I don't want to say I did it all myself, because I did collaborate with people on this record and I worked really closely with my producer, Thomas [Onebane], but I'm taking more of a step into relying on myself and feeling confident in myself and not needing the comfort blanket of the manager, the label, and all the shit around me. Not saying that they aren't useful, but I think I needed to feel proud of myself for what I accomplish on my own. I mean, you were there for me that day when I broke down about it. I was like, “I don't know what I'm fucking doing!” But I figured it out, and I think that's why it feels more celebratory. 

I remember when we first met, you would talk a lot about how much you really loved the performance aspect of music. But when you weren't putting music out, you weren't performing as much. Was that hard? I feel like there's a dopamine feedback loop that comes with performing.

[Performing] is such a weird release for me and it's almost like a channel, because when I would perform, there were no insecurities. I didn't care if someone thought I looked stupid. I was so present and in-the-moment and free. I was so energized, and I love that feeling. So yeah, I do miss it. And I'm still trying to work out the best way for me to do this on a smaller scale. I used to be kind of rambunctious on stage and I feel like that was also part of the emotive feeling. The other day at that show was the first time I'd performed in four or five years. So, I’ve got to figure out what that setup is gonna be, but it definitely is gonna be smaller, that's for sure.

So, when years went by and you had not put out a record, did it ever feel like so much time had passed that it felt impossible to get back into it? Did you think you were ever going to make another album?

It did feel impossible. For a while, I was always telling myself I was going to make a record because I didn't want to admit that maybe my music career was over and that I'd spent all of my life doing this thing. And it was really scary because I didn't go to school, I don't really have any other hobbies, and I think for a while I was like, “What else brings me joy?” I realized so much of my identity was based around being a musician and so much of my happiness was about whether I was doing well or not in music. I think I had to take a step back and be like, “Who is Alex? What do I like to do? Who am I other than this?” I was scared I was never gonna put a record out again and I didn't know what that meant for my identity as a person, but I didn't want to give up on music.

And did the time passing put more pressure on the quality of the work? Like, had it been so long that you felt you had to put out your magnum opus?

Oh, 100 percent. But then I just had to be like, just fucking put it out. Just because I could have sat and done that forever. But luckily, Thomas was really good at reining me back in, because I feel like nothing's ever done, and then I'll overcomplicate things. Instead of putting it on myself for the album to be this big thing, I just let it be a snapshot of where I am in life.

What’s the best piece of advice that you've gotten about creating art or making music?

It's not advice, but I did like that quote that Rick Rubin made about, like, if people aren't hating it, that means there's a problem. I think a lot of what fucked me up was wanting everyone to like what I was doing after King Con and thinking I'm this great artist and all this stuff, but I’d rather just be uniquely myself and be okay with people not connecting with it. And I think that's been kind of freeing, especially with this record because, again, I'm the only one putting pressure on myself and I’m just saying what I want to say and trying to make sure that it resonates with me. I know that maybe it won't connect with every young kid out there, but it's exactly who I am right now as a 36-year-old woman in music. It's very truthful, but it might not be everybody's cup of tea. But as long as I'm saying what I want to say, at the end of the day, I'm happy with it.

You were an artist during that last gasp of the big-money record label days, and now you're doing a record independently, which is how a lot of musicians are doing it. What's the biggest change you've noticed in the industry for artists over that time?

I think the content thing. For me, that's been very overwhelming. Being an independent artist, you're inevitably going to wear way more hats than you would if you had a team around you, but I think this element of content creation and virality and being a personality aside from your music, that's been a big change. I also just think about how many artists seem to be out there now because of the accessibility of making music, which on one hand is fantastic, but I think there’s a lot of people doing it.

The opening song on Bingo! is about your seatmate on a fortuitous flight. Tell me about her.

Ah, yes, Stassia. So, my friend Twiggy and I were on our way home from Vegas at 9 a.m. after a friend's birthday, so we were maybe still a little drunk, and this woman next to us was annoyed with us at first. And my mom kept sending me the book, The Secret, in very mom fashion. I think she forgot she had already sent it, so copies kept showing up. And I was telling Twiggy, “My mom keeps fucking sending me this book. I don't know how to tell her I don't want to read it.” And this woman turns to us and is like, “That book changed my life. I manifest everything in my life. I manifested my new apartment. I go to Vegas and I play online Baccarat and online roulette and I never lose, and it's because I understand energy now.” And I have a history of indulging in the gambling arts, so I was very intrigued because I never win. Then she was like, “This is what I won this weekend.” And she pulled out her purse and there was 15 grand in it! That whole day, Twiggy and I were like, “Fuck, should we read The Secret?” I still haven't read it yet, but I'm also still not winning in the casino, so...

I don’t think I’ve ever gone gambling with you. What is your fascination with casinos?

I find casinos so fascinating and so dark, but also, there's hope in there too. All the shadowy aspects of ourselves come out in casinos and you can't spend too much time there because it really is very dark energy, but there are definitely very real parts of humanity in there that we don't want to look at a lot of times.

They’re kind of like strip clubs in that they itch the baser instincts that we repress in polite society. 

Yeah, and I think a lot of people actually like the feeling of disappointment. I think that there's a lot of beating yourself up and a lot of shame. I think a lot of times, maybe it's more about that feeling of: “Goddammit. I shouldn't have done that. I knew that was going to happen.”

Like the masochism behind it.

Yeah, because there's so much more of that going on than people actually winning. 

Except for Stassia.

Yeah, God bless Stassia. 

Bingo! is out now and it’s the first proper record that you’ve put out in over a decade. Do you see it as the finish line or is this the starting point for whatever is next?

I think it's a bit of both, but it definitely feels like a closing of a chapter and a letting go of certain things that have been holding me back within myself. People are like, “Well, what are you going to do now? Are you going to tour? What's next?” I'm like, I don't fucking know! I'm excited and happy, but I'm also kind of exhausted and I need to tell myself: Just enjoy this moment for a second and then you'll figure out what inspires you next.

This interview has been edited for length and clarity. All photos by me.

---

Follow me: Instagram | Threads | Bluesky | Twitter | Website

Real life: PO Box 11352, Glendale, CA 91226

Shop my merch store.

Get my book SELLOUT at Bookshop, Barnes & Noble, or Amazon.