“What Is Your Why For Everything That You Do?”: An Interview With Oddisee

On 'To What End,' Oddisee asks how far we’re willing to go to chase our dreams and reckons with what reality might have been like if he didn’t take a step back to recontextualize how his career...
By    February 9, 2023

Image via Jasmijn van Buytene for Oddisee

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By the time the pandemic shut down the world in March of 2020, DMV rapper Oddisee had already been voluntarily quarantining himself from his career for three years. After releasing The Odd Tape in 2016 and the Mello Music classic The Iceberg in 2017, he was entirely wiped out. Years of releasing two albums a year, touring for months on end, and rinsing, washing, repeating over and over again had burnt him out. The birth of his daughter gave him a chance to tap out for a bit and realign his focus. When he decided he was ready to finish hibernating, the world had become a shockingly different place. His brilliant new album, To What End, is the result of emerging from this period, of undersold tours that rejuvenated his love of rap and his crisis of confidence that stood between the album and the world.

“The longer I took, the more I started to second guess my abilities,” Oddisee explains. “And then it compounded and it became even more and more difficult to release music.” To combat this fear, he surprise dropped the Odd Cure EP in 2020, a metaphorical dipping of the toe back in the water. It was a call back to projects from the mid-2010s (around the same time as The Odd Tape and The Iceberg) 2015’s The Good Fight and the unimpeachable Alwasta that came the year after. It was a breath of fresh air that continued the artist’s diaristic, sample-heavy rap music, but putting it in the context of those projects makes it all the more clear just how hard Oddisee was pushing himself before he took a step back.

The DC born rapper and producer began circulating mixtapes in his area in the mid-2000s, gaining enough of a following to ink a deal with acclaimed indie label Mello Music Group in 2010. Early projects from that era–mixtapes like Odd Spring and Rock Creek Park–earned him looks in local news outlets and blogs across the country. Oddisee certainly benefited from Mello Music’s built-in cadre of fans, but over the course of his first decade on the mic, he continued to foster an independent fan base; People Hear What They See, from 2012, even earned some modest chart success. By the mid-2010s, Oddisee had built a loyal following of ticket buyers, vinyl connoisseurs, and digital purchasers; in an industry thankless to many, Oddisee was thriving. It came at a cost. He was burnt all the way out.

The refresher was necessary, though longer lasting than he would have liked. That is perhaps why on To What End, he sounds more excited than ever. There’s an energy that courses through the project like a vein, even when Odd is exasperated, sad, angry, mad, or confused. The ethos that propelled Oddisee back to his confident self was a reminder of his fanbase, a devoted group of constituents that knew his discography front and back. “I found a solace and a comfort in knowing I like what I’m making, people like what I’m making, I’m going to make a living off of this, and we’re going to keep doing this,” he says.

To What End asks how far we’re willing to go to chase our dreams, and he reckons with what life might have been like if he didn’t take a step back to recontextualize how his career fit into his life. On the go-go inspired “Try Again,” he raps, “My intention and my callous never been in balance/ It’s a challenge when your talent comes equipped with damage.” It’s unclear to me whether the MC is rapping ‘callous’ or ‘callus,’ but the point hits either way. Oddisee has finally found a way to put out music while mitigating the pain that comes from that very same hustle.Will Schube

It must be nice to have a new one out in the world…

Oddisee: Absolutely, man. It’s really a labor of love that I’m happy to get off my shoulders.

The recording process was pretty much a full year?

Oddisee: Yeah, you could say, give or take. There are tracks that are older that I’ve been working on since my last release, some of which made it on the record. I think I got a track on here that I produced in 2014, but I wrote everything in the past year.

As a way to reflect on the more recent past?

Oddisee: Yeah, I would say so. I would say it’s a reflection on my recent past, but I think with every record, it’s a reflection on everything that’s happened since the last record.

And this is the longest you’ve ever gone between full-length projects. Can you walk me through that hiatus and what you accomplished during that time and why it was necessary?

Oddisee: It started with the birth of my first child, and wanting to take some very much needed time off. My child was the ultimate amazing reason to chill out for a bit and stop doing so much. I wanted to be present for this new chapter in my life, in my wife’s life, and I needed a break, man. I was also pretty much on the verge of burning out. Two records a year for over a decade, a hundred and something to 130 shows a year. I’ve been out of the country six months to a year for almost a decade. It became a lot. My daughter was a blessing because I don’t think I would’ve ever stopped doing that. I needed some time off. I wanted to be inspired again. I wanted to miss making music for the sake of it and not to fulfill a deadline. And I wanted to be present for my family.

How difficult is it to balance that business side and the artistic side, especially in indie rap, which is not the most forgiving subsect of a notoriously difficult industry? How do you navigate that and did you lose that when you were doing two records a year?

Oddisee: I’ve always been very focused on treating my work as work, as a job. I think a lot of creatives who kind of live in the gift and the curse of being our own bosses and not adhering to any type of schedule or structure struggle with this. With my personality, structure has been my best friend. I’ve always put in hours. I work during the day. I don’t work more than eight hours in a day. I don’t work on weekends. My studio is in a separate space from my home so that when I leave, I don’t take work home with me. I’m very serious about private time and family time. I won’t pick up the phone or answer calls after evening hours or on weekends. I take vacations.

It wasn’t too difficult. But with that being said, I think it was really the touring that made life difficult. Even though I was on a schedule, what I was doing in those eight hours that I was at my work desk felt different. It didn’t feel like fun. It felt like work. I don’t mind having the structure of work, but the best marriage is when your work is your love and your passion, so it doesn’t feel like work. It started to feel like work.

When you stepped away, when did you start getting that itch again to get back in the studio?

Oddisee: Right when everybody had to stay in the house. It was like, “Oh, I’m ready to do this. Okay, we can’t go anywhere.” Everybody has their pandemic stories, but I had built a pretty healthy, ecosystem of, make a record, promote the record, tour the record, see how that record interacts with fans in real life in first person, get inspiration from being out on the road and conversing with people, and seeing things and gathering new experiences and hearing bits and pieces of people’s conversations, and seeing just the overall pace and the heartbeat of the world. Not being able to tour threw that whole system out of whack. Probably around 2020 going into 2021 is when I realized that I took too much time off, and it almost became a curse.

I was a very confident artist knowing that what I was making was going to be perceived well, not by everyone, but by the people I needed it to be perceived well by. I found a solace and a comfort in knowing I like what I’m making, people like what I’m making, I’m going to make a living off of this, and we’re going to keep doing this. But the longer I took, the more I started to second guess my abilities. And then it compounded and it became even more and more difficult to release music.

Have you ever had that sort of self-doubt before, even when you were first starting off?

Oddisee: Never. It’s been my superpower and I got hit with it for the first time in my life and it was heavy.

And how do you get past that?

Oddisee: I started to get comfortable being more vulnerable and knowing that if it isn’t received well, it’s okay. One, it’s not the end of the world. Two, I brought in people to be a part of the process. I brought in close friends, I brought in recent acquaintances, I played them loads of music. Most of them assured me that I was tripping. I needed to hear that. I needed to hear that from people who weren’t invested in me. Their livelihoods didn’t depend on mine, and they didn’t need anything from me, so they weren’t scared to tell me their true feelings. I was very adamant about finding those types of people and saying, “Hey, what do you think about this? Give me your honest opinion.” It really, really helped. I just opened it up to a lot of scrutiny from other people because I couldn’t depend on myself to trust my own opinion anymore.

Were these collaborators or people that you just trusted to critique you?

Oddisee: People I just trusted to critique me. Big shout out to Anthony Demby. If you don’t know who that is, he goes by Ant Demby. He came over a lot and listened to a lot of this record from start to finish and gave me his very, very honest opinions. He really helped me reassure my confidence in this album.

Even though you’ve been in Brooklyn for over a decade, do you still associate your music with your DMV roots?

Oddisee: A hundred percent. I’m a DMV artist. There’s no escaping that. The type of music I make, that I’m continuing to make, is from my formative years, my upbringing, my own experiences. Where I was raised and where I grew up shaped my view of the world. It will always be a part of me and a part of my process. I wouldn’t consider myself anything else. I think that regionalism in general is dying in rap music, and I don’t necessarily see that as a bad thing that people don’t have to be pigeon-holed to their region. But if we are still talking about rap under the confines of regionalism, I’m definitely still a DMV rapper.

Speaking about that decimation of regionalism and it being probably for the best, what do you chalk that up to? Is that the internet?

Oddisee: I definitely think it’s the internet. I think that social media and connectivity have shown us that we have far more in common than we have differences. And I think it’s a beautiful thing. Having grown up in beefs between regions, in 90s rap and early 2000s, we definitely focused on a lot of our differences. Differences in production styles, slang, accents, flow, lyricism, and delivery. All of these things took a backseat towards, is it good or is it not? Do I like it or do I not like it? That’s the best place that music should be in. So many other genres of music have had that privilege to be from anywhere and make anything without it being a big deal. It’s finally hip hop’s turn to participate in that.

You can be based in Brooklyn, but still representing the music you grew up on and not have anyone call you inauthentic.

Oddisee: Yeah. It’s been happening for years. Whether it was Drake in Toronto or ASAP’s first album, him having such a heavy influence from the South, but being very Harlem through and through. These things have been in play for years regarding relaxing those stigmas. I can’t speak so much on white America, but in Black America, even as far as fashion, it’s very, very polarizing, where you had to dress a certain way in a certain area, or to identify with your collective or your peer group. Even that has relaxed. I think we owe all of that to social media.

I think a lot of it is a new generation of rappers dressing however the hell they want.

Oddisee: Just exactly how however they want, but also having access to everything at the same time. A lot of the major cities lost their advantage on being able to have access to trends before everyone else. Therefore, creating this superiority and inferiority complex, if people were quote, unquote “behind the trends.” No one has an excuse other than money that keeps them behind the trends. And even money isn’t really an excuse because there’s cheaper versions of everything these days.

When did you begin to realize that you had a full length record on your hand and not just cuts that you recorded in the studio?

Oddisee: I always start my records with the production. The album existed with a title and a full length instrumental in chronological order for a while. And it definitely changed a bit. There’s some songs that I’m guilty of parallel working, which I’m going to try to do differently in 2023. I’ll have a song for the album, but then I will stop producing and start writing, but I still have an itch to produce something else, and then I’ll like it a lot and then I’ll put it on the record. This record is my longest vocal record. I think there are 16 tracks on it.

Have you always written records in order?

Oddisee: From day one. It’s just my personality. I have to have a very realistic goal and work within that, or else I’ll just be all over the place. I get a lot of praise from listeners and peers in the music industry for being prolific, but I think that is only because I’m trying to combat my nature, which is very scatterbrained and all over the place if I allow myself to do that. I have to adhere to very strict templates in order to get done or else I’m all over the place.

You talked a little bit about the vulnerability that you let yourself have, especially on this record. Does that come from the time off and the precarious nature of this industry?

Oddisee: Whether it be with my family or my friends or other artists, I have this reputation that everything is okay all the time, and I always have the answers. That’s just not the case. It’s definitely easier to give other people advice than it is to give yourself advice. I’m a victim of that. I had gotten to this point where, for my own sanity, I had to be more transparent with my views, how I feel, what I think, and that everything is not okay. It doesn’t have to be.

I’ve been in therapy also, and I’ve had a lot of revelations. I’m first generation American on my father’s side, my mother’s African American, so obviously we’ve been here for hundreds of years, but I am first generation on both of my parents’ side to not be born in poverty. I inherited a mentality of thinking that poverty is always around the corner.

Whether or not I was okay or not, I had this mentality that I inherited to toughen up and deal with it and keep it moving. That is what I put out to the rest of the world. Everybody assumed that that’s what it was, when in fact everything wasn’t okay all the time. On this record, I relaxed that a bit and was like, “everything’s not okay.” I think a lot of people are going through that and they need to hear this perspective as much as they hear anything else.

You took time off and then you started going to therapy. I imagine you’re working through that idea of poverty being around the corner. How stressful did it get for you not working and then living your life from that perspective?

Oddisee: I’m always working. That’s the gift and the curse. When I didn’t have touring, I supplemented touring with licensing. I think I licensed the most tracks in my career during the pandemic when I wasn’t able to tour.
Being goal oriented, I’m looking at my daughter, who’s now five, my son who’s a year and four months old, my wife, and I’m like, we need to make more money. My wife laughed when I said that. She was like, “Well what are we going to do?” I was like, “Oh, I got to make more money.” She was like, “Well, that’s easy to say. Everybody wishes they could do that.” I was like, “No, I have to make more money.” So I just put my thinking cap on. I was like, “How can I make more money?” I shifted to licensing.

This past tour was the worst turnout I’ve had in attendance in 10 years of touring, But I sold merch for the first time in my musical career on tour. The income that I made from selling merch, supplemented the loss in ticket sales, and it made the tour very much worth it. It was a tour that I definitely still wanted to go on, even though I was forewarned. I was warned that touring was bleak for indie artists, but I was like, “Look, we got to get back on the horse.” My agent was like, “We got to cancel the US tour.” And I said, “No. No, we’re not canceling the US tour.” And he’s like, “Yeah, but you got to understand this isn’t a you problem.”

I was like, “Look, I’m from the underground. I started booking my own tours on Myspace and sleeping on couches.” Coming from that mentality of poverty, if I have to do that again, that’s what it has to be. I told my band, “Hey, we’re all taking pay cuts on this tour, but if we don’t get out there and meet people who still want to come out to shows and rebuild the momentum, even though it feels like we’re starting from scratch and we feel like we deserve more, guess what? Nobody deserves anything. You deserve what you get, and we got to go out there and do it.”

My band was my opening act, so they kept the fee for opening as well as their fee for being my band. They got money in their pocket every night, and I supplemented everybody’s per diem’s with portions of the merch money. We made it work, and it was great to know that we can tour, we can release records, we can still connect with fans. Even though it felt like a step back, I definitely feel like in 2023 and 2024, it’ll be two steps forward.

I don’t think that a lot of artists go on tour without having merch.

Oddisee: This was the first time I created a web store where people can buy things online. This is the first time that I designed the merch, got it manufactured, handled the logistics, picked it up, and I sold it myself every night. After the show and before the show started, I was selling my merch at the merch table. It was very much a first for me, but it was through therapy getting outside of my comfort zone.

I’m very much an introvert, and the idea of sticking around after a show to converse with people for another hour to an hour and a half was a daunting task that I avoided for years. And this year I was like, “I got to do it. I have to do it.” I can’t just control the relationship I have with the audience by being on the stage and disappearing after the show, which is what I normally do. So I was out there before the show, after the show, just talking to people. It was really, really therapeutic for me.

You see it with acts that have very devoted fan bases like yours. Open Mike Eagle does the same thing, the band WHY? does the same thing. These very personal artists who are willing to let themselves be vulnerable on record, will invite fans to speak with them after the shows, and everyone in the venue lines up. It’s wild.

Oddisee: It can be really, really intense. All of my fears were there. They were validated. There were people who overstepped their boundaries. There were people who had very shrewd perspectives that weren’t my own. There were people whose interpretations of my music, they deemed the main interpretation. I just engaged with all of it. It wasn’t as bad as I thought. All of those things that I was avoiding were there, but it wasn’t nearly as bad as I thought it was going to be. I was in my own head.

A nice metaphor for life, I’d say.

Oddisee: It’s not as bad as you think. It could always be a lot worse.

How do you summarize the philosophy behind To What End?

Oddisee: This album for me is about your goals and how far you’re willing to go for them. Be it good or bad, be it positive or negative. What is your why for everything that you do, and how far are you willing to go for that why?

Did you answer that question on the record?

Oddisee: Of the 16 songs on this album, I tackled that subject in different ways, in different perspectives from the same sphere. There are sides of the record where I’m angry and very much in a go-getter mentality for me and mine at all costs. Then there are sides of it where I ask what the ramifications of that mentality are. There are sides where I talk about the vulnerability of being there for other people’s reasons and other people’s lives and it not being reciprocated. So I think all in all, yes, I answered that question.

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