When Shamir Bailey first showed up in music circles, he was barely out of his teens. The year was 2015, he was living in New York and interning at the "indie-major" label XL Recordings, where he'd even been signed. "I was on a fast track of being a major mainstream pop star," he tells GRAMMY.com in a phone call from his home in Philadelphia. That year, Shamir released the critically beloved debut, Ratchet—a bouncy-ball collection of electro-pop cuts, all topped off with Shamir's cheeky, countertenor vocals. 

Five years later, Shamir is in a markedly different place—musically, spiritually, emotionally. Splitting from XL in 2017, citing creative differences, Shamir self-released a handful of genre-jumping records: 2017's Hope and Revelations, 2018's Resolution, 2019's Be The Yee, Here Comes The Haw, 2020's Cataclysm. Last year, he launched his own label, Accidental Popstar, which incubates and develops burgeoning talent and is home to D.I.Y. performers Southwick, Grant Pavol and Poolblood. 

Now, Shamir has released his latest work, a just-released self-titled album, which serves as a re-entry of sorts into the mainstream music zeitgeist and is, as he said in his publicity materials, "the record that's most me."

Borrowing influences from a range of genres—punk, country, dance and, of course, pop—the self-released Shamir brings the 25-year-old's career full circle with its instantly catchy arrangements, authentic artistry and candid indifference for whatever the music industry thought he should be. 

GRAMMY.com called Shamir up to chat about his latest release, what going independent has taught him as an artist and the best advice he received from one of his heroes: Mandy Moore.

I love the new album, and I'm excited to talk to you about it. You had gone back to Vegas, but now you're in Philly. Is that correct?

I went back to Vegas for... I want to say four months after New York, because I didn't like it. But other than that, I've been in Philly since 2015. I was just basically homeless most of 2015 because I was touring Ratchet nonstop and didn't have a break until the end of 2015. But most of 2015, I knew that I was going to be in Philly. I just loved Philly. I've been here ever since.

I've the always gotten the sense that Philly is a little bit more of a rewarding community for artists and musicians, where New York can be… Well, it's its own kind of stress. Did you found that to be the case?

Yeah. When I came to New York, I was definitely welcome for the music scene. I was living and working at Silent Barn, but I just like how casual the Philly scene was, and how no one was trying to be famous. Everyone was just trying to have fun [and] share music, and it there was no pretension behind it at all whatsoever. And I'm like, "This is me. This is where I'm meant to be."

In many of the interviews I’ve read with you this year, you’ve spoken about being introverted and how that factors into quarantine life. When you look ahead into spending the coming months in quarantine, as a musician, how does that sit with you?

I don't know. I really want to tour. I often like to give myself hiatuses between touring, just to preserve my mental health. I was really ready to go back on the road this year. This is the longest I've ever gone without touring at all. It definitely just the longest I've ever gone just a show, because I still did one-offs last year. But other than that, I'm chilling, like I said. It's really not too different from my normal life, especially since all of my closest friends live in different cities and states, maybe countries. I’m still staying up in their life, digitally.

I’d love to spend some time talking about your transition from working with a major indie label to releasing music independently. What has been the most profound thing that you’ve learned from that journey?

I don't know. I think it's harder for me to say, because I've always felt it was deeply important to be as savvy on the industry and business side of music, as that's the most important for me. From the beginning, I worked on things behind the scenes. A lot of people don't know, during the Ratchet era, I was managing a band and interning at XL as well.

I think if anything, because of that, it made the transition fairly easy for me. I think, for me, it was just better once I started to do things independently in a way, because it's not playing a game of telephone. I think working with a label was like playing a game of telephone, and it's constantly having to explain yourself and set the truth and try to get everyone else on the same mindset that you're on. Which I'm better at now because of the years of experience. But I think, at the beginning, that was just very hard for me. And also, I was just very young and not confident. So, if I wasn't heard, I would just stand down.

Other than that, I think I've had a bit more freedom, and it's been easier. But it's obviously a lot more work, because you're doing everything yourself. You're doing the marketing. I have a publicist, thank God, but you're finding the right publicist for you. But, like I said, I was lucky to have a lot of those connections and understand a lot of that, but I made sure I could.

If you didn't go into artistry itself, what side of the business was interesting to you?

I think A&R and artist development.

That’s really interesting. Starting out as young as you did—that can be an age where you can envision yourself doing multiple things in an industry. You’re just trying to figure out what works for you.

Yeah. I realized artist development worked best. At first, I thought maybe managing, but I was managing up-and-coming artists, and I realized that I was mostly developing them, and the managing side of things, I actually hated. So yeah, even just less than A&R-ing, even though A&R-ers typically are supposed to help develop an artist.

I think because the industry wants fully formed artists these days, A&R is just maybe fewer artists, it's a producer or two, and help with the funding of the record and making sure all of that is intact. But I also like just working with raw material and just helping the artists build off of what's already within them, but just put it in a pretty bottle.

So, when you're developing artists via Accidental Popstar, what do you look for when you bring someone into that network?

First, I'd have a relationship with them, realistically. Everyone that I work was on the label, I have a really deep relationship what. Grant Pavol, I've known him since he was 16. I've been friends with Southwick for the longest, before we started working together, and actually met Paige five years ago when she was interning at NPR. You can actually see her at my Tiny Desk session, when everyone was sitting around me, and then we reconnected a few years later. I was just like, "Hi, nice to meet you." She was like, "We've actually met."

So yeah, I think I have to know the artists inside and out, not even just as an artist, but as a person as well, just so I'm aware of their boundaries. I think the industry in general, when working with artists, doesn’t try to do the work to understand the artist as a person. And so, because of that, they have a very one- or two-dimensional idea of the artist. And I think you have to know the artist as a person as well to get a full scope of who they are as an artist.

To circle back to something that you talked a little bit about in your Billboard interview, you said that were definitely open and hopeful when it comes to perhaps joining a major in the future, now that you have a more well-rounded idea of how the machine works. And part of that is because you want to see a more diverse, intersectional artist roster. Are there any majors—or really any labels at all out there—that you think are doing something right in terms of artist diversity?

Well, I'm not really sure. I have friends that work at majors, but I think for the most part, just being in Philly also has kept me in this bubble away from the majors, which was kind of the point. I came here to focus on myself and my art, and I just also love it as well.

I think now I'm really planning to get an idea of all of the different majors and specifically what they can offer, and specifically what they can offer me. Right now, I'm talking to someone from a major label, and she's been answering every question I have and letting things work, and blah, blah, blah. So, I don't know, I can't really say off the bat specifically any names, but I'm definitely in that process of dwindling down what makes the most sense.

Yeah, we’re living in a time where the industry at large is promising to do better, from a diversity standpoint. Have you seen anything from anyone—whether it’s a company or a specific person—that inspires confidence in you?

Yeah, I'm taking everything with a grain of salt. That's the only reason why I'm even caring about or coming back to reintroducing myself in an accessible way. At the beginning, I was on a fast track of being a major mainstream pop star. But that wasn't necessarily my dream at the time. Maybe not even still now. I just guess I feel more well equipped for it now. But I was like, "I'll step down, and then there would be another black, queer, genderqueer pop star." Right? There has to be. I made such a huge mark. People are literally copying me. People are literally ripping me off. It must happen. And it didn't, and that frustrated me. And so, it's like, "You got to be the change you want to see in the world." I was blessed with this platform, and it never really wavered. So, it would be selfish of me, at this point, not to fully go for it. Do you know what I mean?

Yes, absolutely. Switching gears to the album itself—Shamir experiments with dance, pop, grunge, country, punk. And you’ve said that this the truest representation of you, musically.

Yeah. I finally was able to mix all of those genres in. Does it feel like you're getting whipped?

No, it feels really balanced.

Yeah. That's what I'm most proud of, honestly. It's not so much that it's so different than anything that I've been doing—it's focused, it's super highly focused to the point where I'm able to hit every element without it feeling overwhelming. And I think that's just really it. And so, in that way, it just feels the most me, because it's the most digestible me I think I've been since ever, honestly. I think even in a lot of ways, it's more accessible than even Ratchet, because I think a lot of weird-ass heavy electronic production looks weird in Ratchet.

It's hard to strike that balance, but you make it look easy.

Thank you. Again, this is the longest I've ever worked on a record. Normally, as you've seen in the past, I like to just write the songs, record the songs, put them out there. And this was the first time... even since Ratchet. Ratchet was done very quickly. This is the first time where I wrote the song and let them breathe for a year.

There’s a line that stuck out to me in the single "On My Own." The refrain, "And I don't care to feel like I belong, but you always did." Is that referring to feeling fundamentally out of sync with a partner?

Exactly. I think the song is very generalized, but I think that one specific line is just to that person. To the person, I was like, "Yes. You." They weren't necessarily vain, and I don't think they necessarily felt they need to keep up with the Joneses, but I think they felt the need not to stand out. You know what I mean? And I don't like that. I think that's worse to keeping up with the Joneses to me in a way, because I think... The person was white, I'm just going to say that, but I think there is a certain amount of privilege to being able to still be taken seriously, but also being modest. I think I don't have the privilege [to be] modest, because then I'll just be not heard. You know what I mean? Therefore, I can't be modest, and I think a lack of modesty probably was a lot for that person. 

That's frustrating. And then you might not feel seen.

Well, it's not so much that not even just don't feel seen; it's just like, "This is how I have to navigate, I'm sorry. I've gotten everything that I've gotten right now because I have to navigate like this." I'd rather not. I just think that I'm a low-key person, I'm super introverted, I'm laid-back. I'd rather not, realistically, but I have to.

I was curious—you put out another record, Cataclysm, in March of this year. How did those overlap with each other in terms of the actual writing and recording?

I think Cataclysm, honestly, is very not pop production-wise. It’s very grungy and very fuzzy and very all of those things, but I think some of the best pop songwriting that I've done. There are some songs on there I think that are even poppier than stuff that's on Shamir, but that was the point of Cataclysm. It was supposed to be this very dirtied pop record, because the songs were so very pop and straightforward. So, in that way, that's how they coincide. And often, everyone's just really gravitated towards it as well, because I think I've made the record to sound like the end of the world. I think a lot of people are resonating with that, and I wanted it to sound like an old tape that you found in the ruins of the mess.

Cataclysm wasn't supposed to come out, and when lockdown hit, I was like, "I guess the world needs it." I actually had shot Cataclysm, and I think no one really got it. It's supposed to sound like this. Also, the record is completely a mono as well. It's so weird production-wise, and I'm like, "Yes. It's supposed to sound monochromatic." Yeah, I think it was just timing. I think the universe was just like, "Now. It's supposed to be for now."

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On a lighter note, I was excited that you got to interview Mandy Moore for Billboard.

Oh my God!

How did that come together? Did the editors set you guys up, or had you put in a specific request?

No, the editors set us up. I've been talking about how much I love Mandy Moore my entire career, first and foremost. It all started with the Pitchfork Over/Under piece.

Yeah. It's so funny, and honestly ridiculous. But when they came up with the questions, they have to have gone through my Twitter, which I think I've mentioned in the video, because right before that, I had talked about how much I loved Mandy Moore and specifically Wild Hope. I'm not sure if I single-handedly helped us, but at the time, it wasn't on streaming, but then magically, I want to say two years later, it was. So, I don't know if I single-handedly threw the first brick, but I like to think I did.

And I just didn't think anything of it. And then because they mentioned it in the video, everyone started talking about Mandy again, and then she got on that huge show, on This Is Us, and then there was this whole new resurgence of Mandy Moore. And during that time, we actually followed each other, because she had saw the video, and she's like, "Oh, I don't know." So, we had already been internet friends, at least, for the longest. And then she actually specifically hit me up when "On My Own" came out, and was just like, "I love this song," and everything. Actually, we were DMing yesterday. I love Mandy. She's just the best, she's so sweet, and is just genuinely invested in my career.

Has she given you any career advice, whether in the interview or outside of it, that’s really stuck with you?

I can't even really pick out anything specifically, because that whole specific interview was just giving advice to younger people in the industry. I asked her about balancing acting and music, because I definitely want to get more into acting. She kind of confirmed what I [had] already been feeling. A lot of these things, you just have to go with the flow. You can't do it all at once. Just really, really pace yourself. That's what I've been trying to do. As much as I want to like do it all, I have to cut out time and pace myself.

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