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On envisioning alternatives

Prelude

Dylan Tupper Rupert is a music writer, producer, and podcaster based in Los Angeles, originally from Seattle. She is launching a new interview show called MUSIC PERSON in June on the Talkhouse Network, featuring Karly Hartzman, Hailey Whitters, Merce Lemon, and more. She produces micro music fests called Dylanfest, often in collaboration with restaurant friends. This August, Dylanfest is coming to Orcas Island, WA with James Beard nominee HOULME, and then Ojai, CA with PINYON. She wrote, hosted, and executive produced the latest season of KCRW’s music documentary podcast Lost Notes, called Groupies: Women of the Sunset Strip from the Pill to Punk. She was the founding producer of Bandsplain and has produced other podcasts such as the 33 ⅓ Podcast, and created a documentary about pioneering all-female rock band Fanny for season 2 of Lost Notes. She’s been published by NPR Music, Wildsam, Rolling Stone, MTV News, Billboard, Rookie Mag, and more. She publishes a Substack, Crazy Mystery Catalog, from time to time.

Conversation

On envisioning alternatives

Music writer, producer, and podcaster Dylan Tupper Rupert discusses growing up in the Seattle arts scene, dealing with music industry hierarchy, and imagining the ideal conditions for creativity.

May 27, 2025 -

As told to Ty Maxwell, 2518 words.

Tags: Music, Writing, Beginnings, Identity, Inspiration, Adversity, Creative anxiety.

Do you know that [Dave Hickey] essay “Romancing the Looky-Loos”?

Not off the top of my head.

It’s in his book Air Guitar. He’s describing the difference between spectators and participants and says that one of the things that defines a participant is trying to increase the social value of the things you love—you’re playing a role in getting people interested in something.

I think it’s distinct but related to the role of critic or the role of tastemaker, [which] I kind of shudder to say. My own work and practice is related to being a critic, it’s related to being a producer, it’s related to being a documentarian. But I think there’s a certain type of person that is coming at this subject matter more through the lens of those disciplines… I think a participant is someone who finds what they think is so compelling and can’t live without first, and then tries to reverse-engineer a role within that universe. That’s something I really relate to.

They’re already on the lookout for music or art or theater that’s blowing their minds and thinking about how to throw their weight behind it, instead of just taking from it. They think about, “What else can I do?”

You find something you’re really passionate about and you don’t just want to comment on it or criticize it, but really integrate it into life, in a way. I think that’s something about being a critic or writer—the unspoken, abstract, important thing is not just telling someone why this is important in the context of history or why it’s important in the context of a band’s career or a music scene or something. It’s like, how do you integrate the essence of what this is into life? [laughs]

Listening to your podcast changed the lens of how I’m used to experiencing these [music world] stories from the point of view of the rock stars or the POV of cultural critics who are telling the story from a removed place. The podcast put me in the moment of how these people felt… There are people for whom an art movement or community or scene is a curio, versus people who are invested. It’s a much deeper situation.

It’s like a disease!

When were you stricken?

When I was, like, twelve! I was in the right place at the right time, being just barely a teenager in Seattle, where there was a very robust music community—from the underground to so many house shows and warehouse venues. There were all-ages, above-board nonprofits that I grew up really involved in, and there were programs for youth in music, like a really popular Battle of the Bands. There was a music museum. I grew up on Capitol Hill, a dense neighborhood that was traditionally the artist/music scene neighborhood. I could walk straight into it, you know?

I also was the first generation that had social media, and MySpace and Facebook later on. It connected that [local scene] to the broader world. Sometimes I can’t see myself any other way or living any other life, but sometimes I wonder if that’s just deep imprinting at the moment that my brain was beginning to truly form. Age 12, 13, I literally started going to shows two or three times a week. I recorded them in my high school planner. At the same time, I was discovering I wanted to take a creative path of my own but never felt like I wanted to be a musician. I just never felt that’s what I want to do in this universe of things, but that universe of things became my whole life. Even when I’ve decided to try to step away from it, it doesn’t feel like my life anymore. I really wonder, “Am I just like this because of where I’m from?” It’s a nature versus nurture question for me.

With this podcast and this story, you’re kind of charting this development from the beginnings of rock stardom to the biggest rock stars that had ever existed… How early-70s rock leads into punk is so interesting to me. [Music] becomes more egalitarian, more accessible because you don’t have to be a virtuosic. You just had to have more passion than the average person, more of a will to do things. Was that revelatory to you?

Hugely, hugely, yes. Cannot underestimate. I think it really started to sink in when I was interviewing Pleasant Gehman in her kitchen… Every girl who is like me read I’m with the Band growing up. I really wanted to do my own investigation of these stories. On this other level, I really felt like I had a chip on my shoulder that I wanted to move past. Because I felt like there was a restructuring or a re-lensing of these stories in a very black-and-white, criminal-or-not-criminal sort of way—in response to #MeToo, honestly.

I truly feel like I had the full spectrum of experience. I had the gross older dudes and I also had the really wonderful mentor ones. It was like a palette of watercolors and that is sick that I got that, and not everyone gets that. And I think these women, these groupies that were super young and moving across history as the ’60s turned into the ’70s—which is such a dramatic time in history for youth culture, music, sexual mores, etc.—I felt like they weren’t given that full range of colors to paint and tell their story. They were really getting shown in black and white. A lot of their desires, agency, passion, what they wanted to do with their life in maybe really limited circumstances, was getting flattened down.

With the punk thing, the biggest thing that increased, I think, was the volume and the nuance and the availability and encouragement of female-and-otherwise participation in rock music… Pleasant was just like, “No, it wasn’t like a riot grrrl frame of mind.” It was like, “No, we don’t care about stars anymore.” And that hierarchy-flattening was so crucial.

Another thing that I think is related to this—that completely blew my mind and changed the way that I looked at my own life and my own experience in music, especially as I tried to professionalize and move to LA and everything—was this discussion of the ’60s. It was all somewhat organic, ephemeral. It was a scene; it was Laurel Canyon; you were stumbling into these houses. You just lived in Frank Zappa’s cottage, and then formed a band and you dressed the boys and you helped get them shows and put them in front of the label. But it was all very organic and unofficial. When the music business and the music scene became more industrialized as the ’70s creeped in, a lot of those roles girls were naturally playing became salaried industry jobs. It’s that thing that we’ve probably all experienced where, for example, your friend’s band blows up. They’ve been playing music with their friends their whole life, but suddenly they have line items on the budget to pay for the professional stylist and the roadie and the whatever. That particular moment when art meets industry was culture-wide at the end of the ’60s and the beginning of ’70s… It wasn’t the scene girls that were getting those jobs.

They were breaking down the door for somebody else. Isn’t that always the way with innovation, that somebody does something that is disruptive and then somebody else figures out a way to capitalize on it?

Once it was a little unusual to be a person taking photos at a show. Now, everyone’s taking a photo at a show. As someone who is involved in music journalism and in archival projects, how do you feel about the shifts in a landscape where access to information or documentation of scenes or bands is so much more constant?

In the broader 21st century, we don’t have money and we only sometimes have community. So I feel like every time I’m in a music industry setting, especially in Los Angeles, it is so hyper clear. You go to a buzzed-about show, it is so clear, just the hierarchy in that room. You walk in and you just feel it. It’s different from anywhere else I’ve lived or worked or been a part of a music scene.

Who’s buzzing, anyway? Buzz means different things coming from different hives.

That’s very well put. I feel like when I’m in a room with a lot of music people, on one hand it’s like, “Yeah, this is a community and a cultural moment.” And on the other, “This is an industry as well.” I just feel this contemporary unease about a lot of people being like, “I’m a music person, but what is my role in this?” There’s so few secure spots… It’s such a strange time to be a person like you or me that has decided we’re lifers.

I’m fascinated by all-ages venues and the history of that. My sense is that it’s an edge to be sanded off by business interests, because you can’t make as much at the bar if this show is all ages. It’s not conducive to making money. But we know it’s important and, for the lifer in me, it’s sad to see that go by the wayside.

My friend Evan [Laffer], who has the Jokermen podcast, one of our foundational friendship-bonding conversations was, I was talking about how there’s indoor kids and there’s outdoor kids. [laughs] You know? And not every outdoor kid goes and makes their passion their entire lifestyle. But there is a difference between what it means to participate or consume at a remove versus, one, having the personality type/gumption, and also the opportunities and the access to go and throw yourself into it and make your way. I think those are two fundamental types of people and they both are more or less important than the other in terms of sustaining a love and a care of music. But I think that the opportunities to be the outdoor kid or whatever, they might be waning. But I also am old, so what the fuck do I know?

I do think that there is something that is unique about the modern question of surveillance and constant documentation that threatens the idea of alternative spaces.

Yeah, I hear that.

That ties into the idea of risk—the risk of a space or artwork or music that actually challenges some kinds of norms.

In a world-building frame of mind, sometimes I have to remind myself, “You aren’t put on this earth to constantly fix problems.” Sometimes your role, I think more often than not, is just like you’re saying: to envision alternatives. They probably will never happen, but just making gestures and efforts. I feel like the energy of constantly resisting what’s wrong is really easy to do… But I’m like, “Well, I got so much from my young life out of people that really crafted alternatives and I got to live in those spaces and see how they worked and how people worked together to make them happen.”

For you, Ty, in my mind, you guys in Philly and shit have cheap rent privilege. [laughs] There’s more of an active scene on the East Coast, I think because there’s a lot of mid-sized cities and some major cities that are still affordable to live in and they’re all close to one another. Those conditions and metrics under which you get to hack out this scrappy music life aren’t really available out here because it’s just expensive and competitive. If you were to take a tee from diagnosing what’s wrong with right now and instead envision the alternative, what does that look like for you? What would being a music person look like?

Oh, I don’t know. I mean…

Are you already living the dream?

No, I’m definitely not. [laughs] I think that you’re right to stress the importance of not becoming a non-participant by virtue of feeling defeatist about it… I think about this every day, honestly, because there are things about being a musician or artist that I, to not mince words, find abhorrent, that are unique to the current landscape. I think that it’s important to not give up, but to not go along either. Keep doing stuff, just do it in a way that you are satisfied with and not violating your own standards or your ethics.

Yeah. I’m definitely, like, totally cool with violating the ethics of my own personal code…

No, the thing is we all have been! This isn’t about purity politics.

I grew up in a pretty awesome but also somewhat insular and definitely purity-politics-based music community. I felt like I was being a little bit brave and a little subversive to be like, “Fuck it, I’m going to go get what’s mine. I’m going to go hunt and gather, you guys. If I have to go do something ridiculous, don’t worry, I have a vision. Even if I compromise a little bit, it’s for the greater vision.” I feel like that is an attitude that I’ve had that is very, very welcome in Los Angeles.

These days things are different, but in Seattle it was not like that at all. I think it’s a grunge hangover thing, too. I wouldn’t have known it at the time, but looking back, I really do feel like I grew up in the grunge hangover. It affected a lot of the interpersonal dynamics of the creative community that I grew up in, in really interesting ways. It’s crazy that it’s 2025, so you can be like, “We are a quarter of the way through this fucking century.”

It blows my mind, the long tail of the ’90s and what is possible for people like us. And I think that imprinted in our brains as, “Oh, you can be an independent music person and just figure it out and just keep going and keep trying.” We live in such a different world now, and the thing that we love to do is subsidized by such different forces, or none. I think my ideal world-building situation is one of low overhead. You don’t have to make a career out of this for this to be an integral part of your life, for participants and musicians and creatives that are around the music. You don’t have to turn this into your lifelong career thing to make this sustainable as an integral part of your life. I think that would be the dream.

Dylan Tupper Rupert recommends:

Volunteering regularly, especially as a childless adult who gets to follow their dreams—sacrificing your time and comfort for other living beings keeps you human as you age

Olivia Bee’s photography

Big Ugly by Fust

Meaghan Garvey’s Substack “Scary Cool Sad Goodbye

Walking through Clear Water in a Pool Painted Black by Cookie Mueller

Some Things

Related to Music writer, producer, and podcaster Dylan Tupper Rupert on envisioning alternatives:

Writer Jessica Hopper on continually refining what you do Writer Amanda Petrusich on showing up with genuine curiosity Podcast host Yasi Salek on prioritizing what brings you joy

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