One could argue that Ashley Wool is a natural born talent. Since she wrote her first song to go along with a butterfly rock star character she conceived one Halloween at age 7, her songwriting and performance arts instincts have been hard to ignore.
Fast forward through the years, sprinkle in life’s ups and downs, multiply by her experiences balancing music and theater, and we arrive at the latest single release titled Automatoronic.
Fortunately, I was able to get a few moments out of Ashley’s busy schedule for the below interview feature where we discuss the new release, challenges, technology and more.
Full Q&A along with links and music below.
Where are you from and what style of music do you create? (In your own words, not necessarily in marketing terms or by popular genre classifications.)
I’m from New York. Originally from Westchester County but NYC has my heart. I come from a musical theatre background and like to classify the sort of music I make as “theatrical pop.”
What led you down this path of music and what motivates you to keep going?
I’ve been on this path for so long it feels ridiculous to imagine myself doing anything else. I was one of those kids who always had to be making something—a song, a story, a play. It satisfied the part of my brain that was never satisfied, never stimulated enough by the drudgery of day-to-day life and responsibilities. And I was a pretty weird kid, so singing was also the only thing I ever got attention for that was consistently positive. Which sounds superficial, but that was how I got to the point where I found I could use music as a gateway to connect to people on a deeper level than just “let me show you something I don’t suck at.” And that’s what it’s all about at the end of the day—human connection.
How is this new release different than previous ones? Were you trying to accomplish anything specific?
My first album was recorded in 2006 with live instrumentation on vintage equipment. It was very raw, very real and organic and genuine to the person I was at the time. But there’s also a self-consciousness to that record that I wanted to do away with. There were some very vulnerable songs on that record that, when I listen back on them now, come off as apologies. Like, I’m sorry for having feelings, I’m sorry for being who I am. This upcoming record is the opposite of that. It does get raw and vulnerable, but that vulnerability is expressed with more compassion and forgiveness than guilt and shame. The overall sonic aesthetic of the record reflects that too; it’s much more modern and polished, it’s a sound that isn’t afraid to take up space.
Name one or two challenges you face as an indie musician in this oversaturated, digital music age? How has technology helped you (since we know it does help)?
I think the biggest challenge is balancing the whole “describe your music” demands with not caring too much about what your type or your brand is and how people might judge you pre-emptively. In 2006, when someone called your music “pop,” it had such a negative connotation, especially if you were a woman. Like, I love Britney Spears. She was the It Girl in pop when I was coming of age, and everybody was trying to be her and sound like her. But there was always this underlying narrative that she wasn’t “real” somehow, that her success had nothing to do with her as an artist. And in 2006-7, of course she was really going through it, and being compared to Britney was the worst thing in the world for a woman in pop. Then she made her big comeback with Blackout, and everybody was skeptical of it, but again, everything you heard on the radio for the next three years sounded just like it. I think she’s a macro example of what women in all genres of music, and really all areas of life in general face—nobody can fully trust the fact that we make any significant contributions to our own success. So I guess stereotypes and sexism—yeah, those are the biggest challenges.
But as far as how technology has helped—I would say now we are so connected to so many more people than we ever could have dreamed possible 20 years ago, you can’t help being exposed to diverse groups of people having deeper conversations about the rules we make for ourselves as cultures and societies and asking questions about why things are the way they are and how they could be better. And I think this up and coming generation of kids and teens are naturally more open-minded and curious about expanding and diversifying their cultural horizons as much as they can, because they’ve been able and expected to do so easily from a young age. Gen Z is the “let people enjoy things and be themselves” generation, and the Internet’s omnipresence in their upbringing definitely made that possible. And that’s been a cultural shift that’s helped artists from all backgrounds thrive and find their niches in ways that simply weren’t possible before.
Which do you prefer? Vinyl? CDs? MP3s?
I would say cassettes, specifically because you forgot to mention them, and I’m a big fan of supporting the underdogs. The word “mixtape” also has a very specific, organic cultural connotation that I find very romantic. Cassettes are almost retro enough to be cool again, but only the absolute coolest people who are the furthest ahead of the curve realize it. Obviously, I am one of those cool people. You heard it here first, folks.
How about this one…. Do you prefer Spotify? Apple Music? Bandcamp? Or something else? Why?
Honestly, again, because you didn’t mention it, I really miss classic MySpace for musicians. The interface was extremely user-friendly, the layout was clean, you had endless HTML customization options to make it look however you wanted, and you had everything in one place instead of being spread out over multiple platforms like we are now. It was a real community, too—I found so many artists that I still listen to and am still in touch with because we built actual relationships, not just like-for-like, follow-for-follow type stuff. Nothing has come close to doing everything that MySpace did, as well as MySpace did. But if you made me pick something current in terms of discovering new music, I’d say Spotify.
What was the last song you listened to?
“Helpless” by Ashanti and Ja Rule from The Hamilton Mixtape. (See, there’s that word again, “mixtape.”) And that’s appropriate. There’s a part of my brain that always kind of clicks happily into place when I listen to The Hamilton Mixtape and that song in particular. Of course I come from the musical theatre world, and of course I also grew up loving the pop, hip-hop and R&B of the 90s and early 2000s. But part of me always believed that those two worlds were necessarily and eternally separate. Almost like I had to apologize to one world for my appreciation of the other, because they were just too different. Rent challenged that a little, but I didn’t think I’d see another musical in my lifetime that transcended broader pop culture in any real way. If you had told my teen self that Ashanti and Ja Rule would someday cover a hit musical theatre song that would be played on the radio right along with regular pop songs, I would have thought that sounded too good to be true. When Hamilton came out, it showed me how foolish I’d been to think that and I’ve never been more happy to say I was wrong.
Where is the best place to connect with you online and discover more music?
The central location for all my stuff is www.ashleywool.com, where I just released a batch of pretty cool merch based on my songs. As far as social media, I’m most active on Instagram these days and love finding folks to collaborate with there, but I’ve also recently gotten super into Genius, the site for music facts and lyrics. And of course, I always appreciate followers on Spotify. I put a lot of effort into my themed playlists.
Anything else before we sign off?
“Automatoronic” the new single dropped on March 15!
