Considering how busy New York rapper Homeboy Sandman has been these last couple of years—two EPs, a mixtape, a deluxe edition of 2021 Aesop Rock collab Anjelitu, critically praised new LP Still Champion and partnership with Oakland’s Oakstop Alliance to help create its debut album—you’d think that he’d be enjoying some much-needed downtime to wind down last year and begin this one.

Instead, he surprised fans with another album, 12 Days of Christmas & Dia de Los Reyes, which he released one song at a time starting on Christmas—on his own label, Dirty Looks, no less.

“I’m always making music, you know what I mean?” said the 42-year-old Sandman, whose name is Angel Del Villar II, in a video call from his home in Queens a day before releasing the album. “I’m trying to figure out meaningful ways to disseminate it that feel natural and organic, that don’t feel forced. I could put out an album all the time. … Making music is a lifestyle for me.”

Sandman promised to release at least three albums this year. The music is in his head, even if he doesn’t get it on record, he explained. Staying creative is a form of exercise for him, like doing push-ups.

“I want to get it out because if I don’t get it out, I’m gonna die with most of it not out,” he said. “It does serve a purpose just in boosting my energy and keepin’ my existence tapped into the source, tapped into God, you know, creative energy. I do enjoy disseminating it, though.”

Homeboy Sandman’s recent projects have been made with a sole producer, which he said was happened organically after he found a rhythm. But for 12 Days of Christmas & Dia de Los Reyes, he returned to the way he first started compiling his projects: by working with many of his friends at the same time. So the new album includes collaborations with Mono En Stereo, Peanut Butter Wolf, M.J.R.K.M.S., Illingsworth, NOLAN, K-Nite 13, Locust, Haadoob and Kahlil Cezzane. He said listeners should expect him to continue to mix it up with his projects in 2023 as he begins building out Dirty Looks.

RIFF: What’s your connection to the Bay Area, and how did you get to partner with Oakstop Alliance on its November Royalty Summit compilation? Do you spend much time here? Do you listen to a lot of East Bay artists?

Homeboy Sandman: That [Royalty Summit] came about because the cat that runs Oakstop is from New York, and we grew up together. There was a bunch of talented artists coming through. Plus, I also know and have worked with a lot of talented Bay Area artists. So I was tapped in. The hip-hop community; we connect to each other a lot, so he figured that if he tapped me, I would be able to call on some of the resources that I was connected to, as far as human resources, and that he would be able to tap into the youth that he was working with, with Oakstop.

My lady lived in the Bay. She went to Mills College. She got a masters there, and she really likes it. I spent time in the Bay. I recently spent a few days while I was on a tour in Alameda. I got the Airbnb poppin’, and that was pretty fly. There’s a lot of artists from the Bay that I’ve been a fan of since I was a kid. Hiero obviously comes to mind right away. The Bay has flavor, so it was cool to get out there and just rock with all them cats.

You’re releasing the new album on your own label. You’ve been on Stone’s Throw, and you’re on Mello Music. Why’d you start your own? Why do you want to put your stamp on it?

Homeboy Sandman: It was the most practical. I talked to Mello about putting it out. … Traditionally labels try to avoid the holidays, not only because they figure that people are too distracted to listen to music, but they also figure that coverage is going to be light, because people aren’t even in the office at RIFF. … I actually anticipate working with labels again. Dirty Looks is not at all about marketing; the bottom line is artistic. Labels that I work with all put art at the forefront, but they have different things they take into consideration.

With this particular release, it made sense to put it out on Dirty Looks, given what I just said about the holiday paradigm, or whatever. Dirty Looks is a place where art comes first, and we don’t never think about nothing else. We don’t think about if we drop it at the right time. I want to see it grow. Right now, I’m just putting out Homeboy Sandman joints on it. I got big dreams of tapping the greatest rappers in the world, getting them involved with Dirty Looks.

It’s kind of a legacy thing.

Homeboy Sandman: A legacy, but also something that people can trust, and something that people can depend on if they love rap. The music I’m making and the way I’m trying to do things is basically trying to fill the void that I feel is a thing. I would love for there to be a label that was all the best rappers. I think Mello is the best rap label right now. If I look at Mello’s roster, I think they have the best rappers in rap right now. You look at Oddisee, look at Quelle [Chris], look at Joell Ortiz. These are the most gifted. Open Mike Eagle. I think this roster is the most gifted, and that’s fly.

Dirty Looks is going to be the greatest rappers, and if you come out on Dirty Looks, you’re one of the greatest rappers in the world, straight up. I’m gonna bring some cats out on Dirty Looks that you know, and some cats you never even heard of. You gonna see a cat you’ve never heard of and be like, “Wow! Here’s a rapper I never heard of, and he’s one of the greatest rappers in the world!”

You revived LICE with Aesop Rock last year; will there be any new LICE projects this year?

Homeboy Sandman: There’s some Homeboy Sandman, Aesop Rock music that is not yet released. Comprehensive projects—nothing in mind. … I don’t really foresee that in 2023.

Any plans to work with Open Mike Eagle, who like Aesop Rock, is another Mello Music Group alum, in the future? The last time you guys worked together was on a track for [Aesop Rock’s] The Impossible Kid bonus edition, “Syrup.” You two have a lot of overlap in terms of thematic style.

Homeboy Sandman: I’m a huge fan of Open Mike. We going to be rocking the same show at South by Southwest. It hasn’t been announced yet, but March 17, we’re going to be rocking South by Southwest.

We actually got a track with me, Mike and Mac Lethal that’s not even out that Blockhead did the beat for. That’s why I’m trying to tell you: We got to get joints out. I’m thinking of putting that on this project called Bravery Bunch. It’s gonna be all features. Me and Mike toured years ago—it must have been maybe 2013 or 2014. … I know he’s in L.A. now. We’ve never had the chance to sit down and really build on anything comprehensive as far as any type of collaborative thing. I don’t really know if that’ll ever occur, but he definitely is magnificent, so if that opportunity were to arise, I definitely would look into it.

What inspires you? Some of the songs you’ve written focus on really mundane things that people either overlook or that they take for granted. Why do you think that you specifically gravitate toward those types of things?

Homeboy Sandman: I don’t want my rap to be boring, but this same rap all the time is crazy boring to me. … I don’t get down with the most popular five rap topics, which is a bunch of nonsense to me. It’s stupid. Misogyny’s stupid. Money worship is stupid. Violence is stupid, so much is stupid things. …

I don’t want to be boring. There’s so many things in the world. There’s an infinite, billion, trillion things. Today I got a text from my boy, D-Nice. I put out a track today, “Twelfth Day of Christmas” and said, “Know what I mean/ My towels might look dingy, but they’re dingy and clean,” and he said, “Oh, snap, I can relate to this.” Most things that exist, people have not rapped about yet. It’s a shame that cats are rapping about the same thing. It’s mad corny.

[My goal is to] not be mad corny, which is a fate worse than death, I’m trying to rap about things that people have not rapped about, and also rap about things that people have rapped about in new ways. … I want to add. Add to the history, add on to something you could build on … trying to evolve the art form.

“America the Beautiful” is easily one of the biggest songs you’ve ever recorded. How do you think it holds up all these years later, especially after the last four to six years of turmoil? We’ve had the Flint water crisis. We’ve had serious infrastructure problems. The song tackles these very things. Do you think the song still holds up in that regard?

Homeboy Sandman: The final words of the song are, “Cut the woe is me/ It’s a work in progress, and it may always be.” In the last four years, last eight years, next four years… But I remain crazy grateful. As far as holding up, Jonwayne did that flavored beat. I still like the premise. I catch flak from people close to me for that song, like something’s wrong with being grateful. …

I was with Deca and Randy Mason yesterday. We was kicking raps. … And I was talking to them about how all of us live larger than the pharaohs of Egypt. I could put a phone call in, and they’ll bring food to my door. I got air conditioning, I got toilets and showers. … Historically, we all living crazy large. We all got these paradise existences where we can definitely spend time on growth and everything. But we all look at each other like, “Who got this and got that?” America is a work in progress. “America the Beautiful” is a jam.

You leaned into some very heavy subject matter on 2020’s Don’t Feed the Monster. But on Still Champion and The 12 Days of Christmas, there’s a clear direction on self-care, the importance of health and having a positive outlook. Why the sudden tonal shift?

Homeboy Sandman: A lot of what you hear on Still Champion, the optimism and the power, is due to hittin’ rock bottom on Don’t Feed the Monster. Rock bottom for me was really [2019’s] Dusty before that. You listen to Dusty, and my spirituality is super weak. I’m saying a bunch of nonsense. Mono En Stereo did all the beats and they’re fly, and I’ll always be able to rap what I’m saying, but I was saying stupid things. That was a boring record. … I wasn’t tuned in with God at all.

I really had to break down in a lot of ways. I came out of a relationship that wasn’t serving me. I wasn’t serving myself, a whole bunch of things, and I had to face a lot of fears, and I had to take a lot of time with myself. But doing that, that’s a very important thing to do. I had to do work. I had to do therapy. I had to do dream journaling, and I had to exercise. I needed to call people up, tell them I was sorry, tell my father and my closest homeboys my darkest secrets. Those are what got my soil upturned, and got my soil fertile again so that I could be on the vibe that I’m on now. It is a very different vibe, but it’s very much a result of really facing a monster, facing the demons head-on. Dusty was the result of a lot of not trying to face things, not being real with myself about what I got to work on, what I got to improve, what I’m responsible for in my whole life. I’m happy now. I know I can be optimistic. I’m unstoppable because only I could stop me.

So in a sense, Don’t Feed the Monster was the stepping stone to this more positive-oriented period.

Homeboy Sandman: Definitely. Don’t Feed the Monster was very important, very pivotal. We’re talking about Don’t Feed the Monster as a record, but I’m talking about a time in my life that’s happened to be the time when I did that record. Those songs I wrote when I couldn’t even sleep, and I was like, “At least let me write a record. That way, the night isn’t a nightmare.” The creative process that was taking place with that album helped me so much just as far as getting to the next day.

Hip-hop critic Tim Hoffman contributed to this story. Follow editor Roman Gokhman at Twitter.com/RomiTheWriter.