A conversation with Appleby



Appleby is done moving in secret. For a while, not even his mother knew he was making music. Now, the Chicago singer-songwriter is showing his face and proudly adopting his mother’s maiden name, Appleby, as a representation of unity and humility. Appleby has a knack for writing catchy guitar lines under smooth vocal melodies. Inspired by 21st century powerhouses Adele, Frank Ocean and Chris Martin, his pop sensibility shines through on “Count on You” and “Lady Sunshine,” both from his 2018 album Happiness. Appleby caught up with WNUR to discuss his writing process, athletic childhood and upcoming music.

This conversation has been edited and condensed for clarity.

WNUR: How are you? How has your quarantine been?

I’m good. Each day is a little bit different. Today happens to be a really good day, man. I just came back from San Luis Obispo, and it was a great reset. I hadn’t really changed my scenery since the top of quarantine. It was exactly what I needed. I think I’ve experienced all the emotions I’ve probably ever experienced in my entire life inside of the last four months. One of the things that I realized is that I’ve grown a lot. I needed this time to figure out a lot of shit personally as well as creatively. I haven’t been affected as much as other people, and that feels like a huge blessing. I’ve used this time to figure out what my vision is and realize why I’m making music and the purpose behind it. 

WNUR: How has isolation changed your creative process, if at all? 

I’m a part of that group of artists that are all DIY and accustomed to doing things at home, so my living space has always doubled as a creative space. It was never like I needed to go out to a studio in order to feel creative. I love rolling out of bed and laying vocals down or writing. Because I’m not able to pull from conversations on a day-to-day basis or from a party or from a picnic or something like that, it’s forced me to focus on memories or visuals and then soundtrack that with my writing. So now I’m trying to focus on…what have I experienced? What haven’t I talked about? What does that look like? What did the trees smell like? How many cars were around me? Was the air thick? It’s sound tracking those experiences. It’s been challenging. It’s been thrilling. It’s been exciting. I’ve discovered exactly what it is that I gravitate toward to pull out the most honest version of myself artistically. I can just experiment with that. One of the greatest things with music is we transition quite naturally into the digital space. With Zoom and an app called Audiomovers, you feel as if you’re in the same room with the person. So in terms of generating ideas, it’s just as easy as it was previously, except it’s a bit more comfortable.

WNUR: Obviously so much is going on right now — it’s like a never-ending news cycle. Do you find it easier or more challenging to write music right now?

When quarantine first hit, it’s kind of fun for everybody. We all get to have this joyous moment of, like, let’s see what it’s like when we get to focus for a week. You see all these different fun games that people are doing and all these exciting things, and then all of a sudden, you start to realize this isn’t going to change. And so you kind of go through each day, at least for me, with some version of depression — a state of staleness, of static. That felt really jarring as a creative person because that weight of trying to be productive can feel like too much pressure. Then the social media element kicks in, and for me, that’s one of the hardest moments, because as a Black person, you get a constant barrage of horrific imagery. It’s great when friends and family reach out to show love and show their support, but when you’re watching a lot of these different videos and seeing these different faces…that could be your cousin; that could be your sister; that could be your brother; that could be your mom. It became a lot because I was questioning whether what I do is important in comparison to this time period. And thinking, ‘how can I help, and how can I not overwhelm myself?’ I’m not trying to pretend like I have my act together or that I have all the answers. I’m talking about it with friends and family and my loved ones and the people that I care about, just trying to navigate it the best we can.

WNUR: You moved around a lot growing up. What was that like?

Yeah, so I was born in D.C. My family’s from Ohio. My mom and I moved to Steger, which is in suburban Illinois. It’s so tiny, nobody really knows about it. I moved from there to Miami, because I grew up playing tennis, and I wanted to go to a high school that would be forgiving of a lot of travel. At the beginning of my sophomore year, I ended up going to a tennis academy and spent several years down there until I moved back to Illinois. It was in the burbs of Illinois that I became an artist. So Chicago is home to me not because I grew up in the city or anything like that, but because I became an artist in Illinois. Chicago was the first place where I recorded in a studio and made friends that were artists. It was where I felt accepted and embraced creatively. It’ll always have a special place in my heart because if it weren’t for Chicago, I wouldn’t be the artist that I am today.

WNUR: And now you live in L.A. Are there any distinct differences between the music scene there versus Chicago?

Chicago is one of the best cities for creativity. It’s big and metropolitan but it doesn’t feel like you’re competing with the behemoths that are LA or New York, where it feels like the city is swallowing you whole because everybody’s a creative. Chicago is a city where there are many different styles of people and energy, but there’s also no big labels there. There’s no heaviness to the industry like in New York or LA, so it allows us to find our thing and hone in on it. However, a lot of us end up migrating outward because Chicago can also be limiting due to the fact that there isn’t as much industry as LA or New York. And so really, when you build that foundation, it’s wonderful to move out if it makes sense for you. If it doesn’t, there’s a lot of wonderfully talented people that remain there.

WNUR: Maybe the lack of industry is why the DIY scene is so big in Chicago.

Yeah, and there’s a wide array of people that make all types of music in Chicago, and it doesn’t feel like you’re pushed to be a particular type of artist in Chicago versus when you’re in LA. There is an overwhelming feeling of what’s working in LA: a style and a vibe and a sound… things like that. In Chicago, there’s just a multitude of people doing whatever. It feels like I do my thing, you do your thing. It’s such a loving community, and because it’s not an industry hub, you all circle around each other just based off of being in the same space with people. Chances are you know one or two people from every circle that exists in Chicago, and you run into people all the time at an art gallery or at a house party or at a show. Chicago is small in that way.

WNUR: Are there any specific spots in Chicago that are important to you?

Classic Studios, which is the first studio that I recorded in. My first session ever was with Smino, and I was making very weird music. He was like, “Yo, your music’s weird bro, but you’re tight.” My next Chicago landmark is the Nice Work office. And Eric Montanez and Pat Corcoran took me under their wings. Eric brought me to a Saba concert the day we met. And that introduced me to the entire Chicago scene in one night. It was like meeting all of your heroes in one space. Other than that, it’s the room in which I became an artist, where my mom lives in Elgin. It’s where I first tried to write a song, and it was terrible. That place is calming to me. Before it was about numbers, before it was about deals, before it was about the politics and all that kind of stuff, this was just a boy trying to figure out why he’s sad and find the words to express it.

WNUR: As someone who grew up playing tennis, do you think that sports and music have anything in common? Was there anything that you learned from being a serious athlete that you can apply to making music?

One of the things that was really important to me was the dedication that I put into tennis. It’s five to eight hours a day, five to six days a week. And you don’t get a pat on the back for any of that. Music is this long grind to the one or two moments that people congratulate you for. And so everything leading up to that is the 10,000 hours put into writing the one song that could change somebody’s life or change my life or get me that pat on the back. For me, what it displays is that when you care about something, you’ll do it regardless of whether people are watching you. I was playing tennis for me, not for the benefits that tennis brought. I’m doing the same thing for music. It’s not for the perks that come with music, it’s because I need it as a therapeutic release. The biggest thing is developing that discipline. Somebody once said to me that learning how to lose is something that an athlete knows that most people don’t. As an artist, you might drop a song or an album that completely flops. As an athlete, we’ve all had those days where we screw up or we lose or whatever. That can’t stop us from going back to work the next day and practicing and working so that we don’t lose again. 

WNUR: I’ve been listening to the audiobook of Outliers by Malcolm Gladwell, which somewhat dispels the idea of the “child prodigy.” He talks a lot about the 10,000-hour theory. It’s all practice.

Yeah. It’s about finding your recipe that’s going to make you different than the next person, and then working at that until people think that what you do comes naturally.

WNUR: How would you describe your music to someone who has never heard it?

I make music that’s not glamorous — it’s honest. It’s about as stripped back as it can be. It’s like a bottle of emotion, and you can open it up if you feel like you’re in the mood to hear something that’ll probably bring your energy down. I gravitate toward music that feels comforting and feels like a hug — slower tempo, more somber, more sad, more raw of an emotional place. But it’s also childlike with a little wonder in it and not so overly sad that it feels depressing to listen to.

WNUR: Do you do any of the instrumentation on your music?

The music coming up is some stuff that I’ve actually done some co-production on, which I’m super excited about because that’s a new development for me as an artist. I started by buying an Arturia KeyLab at the top of this year to try and create chord progressions for myself to write to. Through doing that, I ended up finally finding a rhythm of generating not only just one idea, but writing to that idea and then keeping that momentum. There will be upcoming songs that are some of my favorites I’ve ever written on which I have a physical hand in production, but most of the previous music has been pretty hands-off for me besides lightly arranging and moving some claps or snaps or snares around. Now I’m a bit more hands-on, and I don’t really foresee myself taking the foot off the gas.

WNUR: Do you typically start off with a chord progression and then write, or do you write first and then put it to music?

I seldom write before putting to music. There have been two moments inside of quarantine where I’ve had expressly vivid dreams and then wrote them down in order to write a song about it. I’ve done that successfully twice. Typically, I need to hear the music, which brings out a set of words or evokes a certain emotion. From there, I end up generating what I call a log line. If you’ve ever been on IMDb before, there’s two to three lines that describe what every movie is about. I do that for every single song that I write. Every song I write has two to three sentences at the top of it that I find after I’ve figured out the melody or figured out the emotion that I’m trying to go for. I soundtrack that memory or emotion, and it can totally change, but it allows me to write 15 songs and not have them all be about the same thing. 

WNUR: Why did you decide to use your mother’s maiden name as your artist name?

For a very long period of time, when I first started making music, no one knew I made music. My friends didn’t know. My family didn’t know. I was making music for myself because I needed a way to express my emotions after quitting tennis. I was lost as a person, lacking a purpose, and I didn’t realize that tennis gave me purpose. When I found music, I didn’t want to jeopardize that by telling anybody that I was doing it, so I just did it for myself for eight months before I stepped into the studio. And when I stepped into the studio and it finally became this thing that I was going to share, I didn’t think that any creative thing that I came up with would be cool enough 15 years from now. I thought I wasn’t going to tell my family that I was making music for a while until it felt real to me. Calling myself Appleby was a way for me to keep them involved without being aware of it, and also for me to maintain humility because, no matter how big I get as an artist, if I’m being a jackass or if I’m presenting myself in ways that I didn’t grow up, I’m ruining my family’s name. It puts a little bit of pressure on me, but it’s a good kind of pressure to maintain understanding that you are a reflection of your family. And I want to be a positive reflection. Calling myself Appleby was also a way for me to hold my family in my heart everywhere I went, and now they’re a part of it all when they see the name on websites or in a magazine. It’s their last name. It’s a shared experience for us all, so it feels as if it’s bigger than me.

WNUR: For a while, you didn’t show your face publicly. What made you decide to change that?

So initially, because I was keeping it to myself, it was important for my family and friends to not stumble on it. I knew when I first started making music that it wasn’t my destination sonically; it was just my entry point. I’ve always watched people not accept sonic changes of artists if they already know them visually as this one thing. So I didn’t want my audience to look at me as the sound was changing and be like, “Oh, you don’t reflect that sound.” It was also kinda fun because it was a way to promote things in a more unique way than like, “Here’s my face.” And so, it wasn’t until I experienced happiness that I felt comfortable showing my face, because I didn’t want to hide from the music anymore. I was accepting of myself and ready to put my face in front of it. 

WNUR: Have you found showing your face to be a relief?

Yeah. Part of me enjoys showing my face and then part of me recognizes that it still weirds me out, like, looking at my Instagram and seeing nothing but photos of myself. I mean, I’m comfortable with the way I look, and I’m comfortable making the way I look equally as important as the music that I make. I also understand that it’s not common for a lot of Black men to be open and vulnerable in the way that I am musically, and so it’s great now for people to see that these types of artists exist, that these types of people exist and that this type of expression for a Black male is happening and not hiding. 

WNUR: The lyrics to your song “Like U” are very specifically targeted at someone. What was the inspiration behind it? 

That song is about my dad, whom I don’t actually have a relationship with. One of the weirdest things about that is while I look more like my mom now, I grew up looking exactly like my dad. I don’t know what my dad looks like now because I haven’t seen him in years, but I’m sure that hasn’t changed much as I’ve aged and as he’s aged. You know when you look in the mirror or you jump out the shower and you look at yourself or you walk past a store and you see yourself in reflection of the window? It felt weird to me that I would look like a person that I don’t have a relationship with. I’d find myself repeating actions of his, and I’d try to separate myself from him. So the song stems from the idea, “I may be young, I may be dumb/But I’m nothing like you.” I can look like you, I can talk like you from time to time, I may even act like you from time to time, but you and I are not the same people. I’m not like you. I wanted to make a song about that, but I didn’t want to make it so it couldn’t work as a love song. I wanted to write it in a way that allows for people to listen to it and interpret it in their own way. 

WNUR: You recently put out “Luck.” How did that song come about? Is it part of a larger project?

I wrote that song in the last apartment I lived in before moving out to LA. I wrote it on a really stale night within like 15 minutes, laid it all down and went to sleep with it on loop. I woke up the next day feeling like this was like an amazing song that I not only needed to write but needed to hear, and it brought me a lot of comfort. Over the course of a year, I could never get the production right — I went through many different versions and iterations. And then one night inside of quarantine, I heard a specific version that moved me in the same way that it did the first month I wrote it, and I felt like it needed to come out. The song is a great gap between my album Happiness and what’s to come. 

WNUR: Who are your biggest influences? 

My number one favorite artist is Adele. I love Frank Ocean, Lorde, Chris Martin and then a giant list of people beyond that, but those are my staples. The obvious artists that I gravitate to outside of those are FKA twigs and Sampha. I love the idea of being in a space where you don’t necessarily need to occupy a cultural relevance or mainstream relevance, but you can do exactly what you love to do. It’s like FKA twigs collaborating with Future. It’s odd, but she can dabble in that because her audience allows her the freedom to do that and then not alter the perception of who she is as an artist. I want to make music while not having to be culturally relevant or play the game of radio or be mainstream.

WNUR: What are your plans for the future?

I’m now at that point where I’m sitting on a catalogue of music that I want to have out, so it’s now figuring out what will come first. It’s likely to be one of the two songs I had a dream about and then wrote, but I don’t know quite yet. I’ll be releasing an EP and giving the audience an experience with each song I put out. Beyond that, I’m trying to get better at my art and do things that benefit not just myself, finding ways to be effective as a community leader.