Dylan Owen is an independent rap artist from New York City. Owen entered the music scene after leaving Cornell University in 2011 to develop his career, and, by 2012, had been named one of Billboard’s Next Big Sound Artists. He has since been featured in HotNewHipHop, RevoltTV, and Huffington Post, with his songs appearing alongside brands such as PepsiCo, MTV, and WWE Smackdown. He has shared stages with Mac Miller, Wiz Khalifa, Yelawolf, Chiddy Bang, and Logic, among others. His music has been streamed upwards of 11,000,000 times on Spotify. His newest LP Holes in Our Stories was released alongside a companion book in 2019.
Amelia Spalter: Plenty of people download music software with the intention of becoming a professional, but very few do it. How do you cope with the never-ending pressure of being a self-supporting independent artist?
Dylan Owen: It’s very easy to lose perspective and get lost in the “how” of making this work; things like the changing climate of the music industry, streaming, what sort of project to do next, all these types of things. You always have to be on the cutting edge of technology, but I don’t let that lead my decision making, I let the art drive what I do. I still have to address those questions, but I reframe them as “How do I take my art and talk about it in a way that makes sense for our Instagram era or our Spotify era?” I try to let the art lead even in moments where it doesn’t feel like I’ll be able to sustain a profitable business. It’s ok, because I’m not in this for the money, I’m in it for the long haul.
AS: Your dedication to the art shows in every aspect of your work, because you touch everything from the beats to the album art. What was the most unexpected obstacle you’ve faced in remaining independent with every facet of your work?
DO: Something that I’ve been struggling with just this past year is time management. I do everything myself, from booking the shows and choosing what songs I’m going to release to directing all of the music creation. I start it in my bedroom, then I’ll find musicians to play with and I’ll go to their house and record them. So many friends help with all this, so I want to give them all credit, everyone contributing is what makes it come out so good in the end, from Gabe Valle playing keys and violin on the recordings, Skinny Atlas making the beats and producing, Tommy McCormick who helps us record, Jason Moss who mixes the songs, the list goes on and on. My buddy Tom Flynn, a high school friend, does all my design. He designed the shirts and my vinyl and my book. So props to all them. Time management becomes a struggle, even with everyone pitching in, because I need to physically be there a lot of the time for us to do all these things. So just the basics of physically going from location to location adds up, timewise. It’s hard to feel sure I’m doing the right things with my time. When you have a manager or a boss telling you, “Yes, this is what you should work on. This is how you should prioritize your time,” that’s a lot easier than directing your own open-ended schedule, you know?
AS: How do you manage to keep your fanbase so tight knit even as it continues to expand?
DO: It’s just the nature of the music, the way it sounds, and how sincere and personal it is to my life. It’s also the way that I interact with my fans online, I guess. I’m always talking to them at events and we’re always messaging back and forth. We message about serious things in their lives, and how the music has affected them, and that leads to there being this connection that’s bigger and deeper than the music. People will travel a long way to see my shows, partially because I don’t really play that often. So, like in New York the other night, a listener drove from outside of Philadelphia through four hours of traffic just to be at the listening party. And he’d been at the last few New York shows too. That’s amazing to me, and it’s important to me as well, for it to be a community. The community is the most fulfilling aspect of what I do.
AS: The unabashed vulnerability in your work must make it that much easier for your community to open up to you. You are startlingly transparent, especially for a public figure. How do you decide what real-life details you will share such as what locations will be revealed or who gets a pseudonym?
DO: It’s funny because on a personal level, with my friends, I’m actually not that way at all. The reason why I’m so vulnerable in my music is it’s the one place in my life where I express myself that way. So it’s really funny meeting people from the opposite direction, where they only know me through my music, because they probably have a more intimate perception of me than some people who really know me. But I think it’s valuable to be that vulnerable because I hope that it inspires other people to be that way, and to show that it’s okay to have whatever feelings you have and to express them and talk openly about them.
I try to, of course, limit what I’ll reveal in the event that it would ever be hurtful to somebody. And if I use a real name, I always keep it to first names. This is maybe more of a writing technique, but I also try to limit my work to a certain set of characters. For example, I don’t just talk about every friend I’ve ever had by name in my music. I keep it within my family tree and people I feel have been particularly formative in my life. When you listen, you can notice that there are no more than five or six of them named across my albums.
AS: The content of your music is so diverse, but the quality is always unwaveringly consistent. Is this because you’re loyal to the same production team?
DO: I honestly think it comes from taking so long to make each of these albums. I’ve gone through them no fewer than thousands of times by the point that they’re released. With my writing and recording, I will have a single beat or a progression that I’m messing with, and I’ll write the lyrics to it for so long. For some of these songs, I was writing the lyrics for three or four years. I’m not kidding.
Every time I’m walking, I might listen to that same beat. I perform the song live in my head and fix little parts and memorize it. I obsessively memorize the words without ever saying them out loud, never needing to write them down until I’m really comfortable with that piece. Then I’ll write it down and tweak little things, and only then I might do it out loud for the first time. I just dig and dig and dig. A lot of those songs don’t ever even come out, because I get them 90% of the way there, and then something doesn’t click for me and I can’t finish it. I think that’s one of the biggest things that people who listen to my music probably don’t know about me, is just how many nearly finished pieces there are that I haven’t posted.
AS: All of your other album titles leading up to Holes in Our Stories had upbeat, optimistic titles. The tone of this entire album is a little darker. Why is that?
DO: That was pretty intentional. I wanted the title to have some anxiety in it. I don’t know exactly how to explain it, but I wanted it to feel a little bit unrealized, if that makes sense. A lot of my titles are full phrases, whereas this one requires a little bit more explanation. It’s a purer metaphor. I wanted to show what the album represents to me, which is that these last few years have been a struggle, and I haven’t really gotten where I want to in life with my own emotions, and that there are so many things left unresolved. That is the whole point of the album. The outro is this scrappy little acoustic song that’s pretty short and is supposed to feel like a conclusion that doesn’t really arrive anywhere, because that’s what I’m going for with the theme, too. There are things in your life that are not going to feel tidy and wrapped up, and you need to be able to let them go and move on from them so you can get to the next thing while there’s still time.
AS: Where do you summon the drive to move on to the next thing even after going through discouraging periods like that?
DO: One of the things that always kicks me into gear are messages I get from fans. If I see a fan has gotten the lyrics tattooed, or a fan drives four hours for a show, or something like that, it wakes me up and makes me realize that the music can really impact people if I put the work in and stay true to my vision. Those things always let me see that there’s a bigger world out there. Playing live shows really inspires me as well, because sonically, when I’m performing live, I can see the songs that I’ve heard a billion times while recording in a different way. Getting out of my comfort zone a little bit inspires me to write, helps me feel like, “Oh, there’s a million more things I could try.”
AS: Once you became a professional musician with a dedicated following, what myths about the industry were you most surprised to find untrue?
DO: A big myth is that, “You’re not able to create radio quality stuff if you don’t have crazy resources,” and that’s not the case at all. You really can, even with just your laptop. I always strive to make my stuff as good as I can, no matter what, even if it takes a janky way to get there. I always think we should be able to get it to sound and look just as good as anything else that’s out there. And, of course, there are minor limitations, but overall it’s just a big myth.
Another myth, on the reverse side of that, a lot of the really well-known established artists do things in a more off-the-cuff way than I had always thought. I remember hearing this story about Lady Gaga recording background vocals for one of her songs on a MacBook laptop microphone, just through the mic, and they used it in the final song. There are a lot of stories like that. It makes me realize that if you have a laptop with music software and you’ve put the work in to know what you’re doing, then you have all the tools that everyone else has. Once you have the music, you can get the word out there on your own. It definitely takes longer and it’s a lot harder, but there is no physical wall between you and the music industry. It’s just a matter of reaching the people who listen to music.
AS: Who is the most exciting person you’ve shared a stage with so far?
DO: I would have to say Mac Miller for sure, rest in peace Mac Miller. It was one of the craziest shows I’ve ever played. He sold it out in advance. It was up in Ithaca, New York and it was so packed that they had to call the fire marshal during Mac Miller’s set and kick everybody out because people kept flooding in past the point of it being a fire hazard. This was right when Mac Miller was blowing up huge and everyone was talking about him, so it was really cool to play with him. It’s actually even cooler in retrospect.
AS: Now that you’ve wrapped up your tour, what’s next?
DO: Next is releasing a lot more music, a lot more consistently. My whole career has been these big conceptual albums years apart, and I want to start just releasing, even if it means one song at a time. I don’t like that I’m working so hard behind the scenes, creating 24/7, straight through weekends, going all the time, but fans still approach me like, “Dude, I can’t believe you quit music.” Releasing more consistently will be a great opportunity to show listeners a whole other side to me. I also want to do more listening parties outside of New York. I’m not sure how yet, logistically, but my dream would be to do those in as many cities as we can. I would love getting to meet listeners in those other cities, and hopefully meeting some new listeners to spread the word, too.
AS: As a musician, what song do you recommend everyone add to their playlists right now?
DO: Of my stuff, “The Glory Years,” is probably the one I’m most proud of at this point in time. As far as other musicians go, there’s a composer named Gavin Luke who plays the piano and I love him. I’ve been listening to him on the subway and stuff because he’s so relaxing. There’s an artist named Lucy Dacus, she’s amazing. Her lyrics are so striking and metaphorical and deep and beautiful. There’s a rapper named Sol, from Seattle, he’s been releasing a lot of music recently. There’s an artist named Abhi the Nomad who’s an up and comer too*. I listen to Watsky, he’s great. I’m a big Bright Eyes fan, and they have a new album this year, which I’m excited about. I’m all over the place, but the common thread for me is the lyrics. I love when there’s interesting writing. *Dylan has since released “Bruises”, a single featuring Abhi the Nomad.
AS: What is the best way for fans of independent artists to support the music?
DO: I want listeners of my music and everyone’s music to know that it makes a big difference and has a big impact when you message an artist and say, “I love the music. I’m listening out here in Idaho,” or whatever. That really changes things. If you want to know how to help directly, streaming songs on Spotify really helps independent artists. To make a long story short, the more you listen to it, the more it’s going to show up in recommended songs for other people, which helps us attract new listeners. Obviously coming to shows makes a huge difference too and is the best way to connect. For me, it’s just as much the listening parties as the shows, I love connecting with fans. Whether it’s a coffee shop or a stadium, you’re all invited.
*This interview has been edited for length and clarity.