Aesop Rock (center) with DJ Big Whiz and Rob Sonic are Hail Mary Mallon. Photo: Chrissy Piper

Some rappers spend entire careers developing their voice and image, but these things seem to have come naturally to Aesop Rock. Bred in New York and currently resting his head in San Francisco, the underground favorite came into the game more than a decade ago with a meticulously crafted, insular world that seemed to exist only in his head and rhyme pages; one where hazily grim images (tugboats, dental braces) are magnified by reoccurrence and his booming baritone until they seem almost mythological in scope. Recently the borders of that world have broadened, or maybe Aesop has stepped outside of it completely, thanks to a late-career immersion in the collaborative process. He’s teamed with fellow rapper Rob Sonic and DJ Big Wiz to form the group Hail Mary Mallon, (who just released the surprisingly jovial Are You Gonna Eat That?) and lately, he’s been sharing the stage with Juno-approved folkie Kimya Dawson. Hive caught up with Aesop to talk about his perceived darkness and learning how to age gracefully in hip-hop.

Is Are You Gonna Eat That? the closest you’ve come to making a party album?

[Laughs] Yeah, a lot of people have been saying it’s more fun then they would expect from me, whatever that means. We kept thinking it was sinister and then people heard and they were like, “This is fun!” Whoops! Maybe it’s just because it was a group project. The fact that you have two people rapping allows you to do stuff with the patterns and [do] a lot of stuff you don’t even think about when you’re by yourself. So that opened the door to have more playful elements. Even on a more sinister track we can have playful back and forth on the rhymes. But yeah, I guess I managed to make something fun. That’s cool — fun is not something I’m used to.

Just from following you on Twitter, it seems like you’re a pretty happy guy, and yet your music is so incredibly dark.

I’ve gotten that forever when people meet me. I don’t know what they’re expecting but the fact that I laugh and stuff kinda puts people off. I don’t know, whenever I sit to write it’s always darker, more aggressive stuff that sticks with me. The fun part is being as sinister as possible and really going there with the lyrics.

Did you and Rob write separately or together for this project?

The bulk of it was me and Rob just sitting in this apartment in San Francisco together. It’s interesting — I’ve always written alone by myself in a room, fully boxed up, but this is the first time where a lot of the writing was knocked out with us in the same room. With most people, I would feel a weird pressure to write around them, but me and Rob just know each other real well so it doesn’t matter. I can [write] slow or fast, or I can just kinda fuck up and there’s no pressure.

You’re kinda functioning as a free agent now as far as the label situation goes.

Yeah, I don’t know what the fuck I’m gonna do; we’ll see what happens. I’m pretty over the record industry. The Hail Mary Mallon stuff is signed to Rhymesayers so anything that continues under that name will be over there for a little bit. But none of the other projects I’m working on have homes as of now. They have potential homes, but nothing [confirmed]. I’ve also not thought about that at all for the last couple years. I’ve just been making shit and not worrying about where it’ll come out.

How have people been responding to the Kimya Dawson tour? You guys have such different sounds and, I assume, fanbases.

We do, obviously, but I think there’s a lot in common there, too, that once people have heard some of the stuff we did together, people are like, “Oh yeah, that makes total sense.” It’s weird for people who are just hell bent on one genre but a lot of the writing style, the foundation for what she does and what I do, is pretty similar. The response has been awesome though to be honest. You get a couple people at every show that are like, “What the fuck is this?” But for the most part you get people who are like, “That was fucking badass.” We’re both into it and enjoying making the songs.

It’s always fascinated me how you came out with such a fully formed and unprecedented rap style. Where did that even come from?

I don’t know; I probably listened to the same things anyone my age did. [I've] always been interested in keeping things different – a little on the weird side if possible. That’s part of the fun for me — hearing what’s going on out there and then twisting it into my world.

It seems like there was a stretch in the ’90s where more of an emphasis or pride was placed on each rapper having his own distinct style.

Yeah, there was definitely a period where the differences were celebrated more. You had groups that could bring an entire image to the table — like an X-Clan or a Pharcyde or Tribe Called Quest — and they’d come with an entire rap style. Not just an East Coast or West Coast thing but a fully functioning aesthetic. And then at some point everyone started trying to do the same thing. Just cut-and-paste sounding where the beat could be any beat and the lyrics could be any rapper out there.

When you were coming up did you envision yourself having a more traditional hip-hop audience, coexisting with the Pharcydes and the stuff you were listening to?

No, I didn’t know who the fuck was gonna like my shit. I didn’t know if anyone [would].  So from day one, anyone who’s been supportive, I’ve been into it. I don’t know what my fanbase is or how they can be described but I’m happy to have anyone. I’ve seen people get upset because they feel like they’re not appealing to the people they wanted to but if there’s anyone out there that’s supporting what you do, then it’s something to be thankful for. I don’t care who comes, it’s just crazy that I’ve been able to do it for as long as I have. I never really planned on being a rapper, I just kinda did it and then people started liking it. I went to college, got a job. Not a good job or anything but I was fully set to be an office employee for my life.

What was it that sparked that transformation from the desk job guy into a full time rapper?

Well, I was always rapping but it was never my plan to rap and be successful. At some point I was out of college, back in New York City, and going to open mics. Somewhere along the line I had a tape and people actually liked it. People around New York started buzzing a little with my stuff and at some point I was like, “Maybe I’ll try this.” I signed my first record contract and I thought, “Maybe I’ll quit my job for a year and see what happens. If a year passes and I’m in the hole and fucking dying, I’ll just go get a job again.” I’m not above working, whereas a lot of people will be like “I’m a fucking rapper!” They’re like, 15, and they decide that they’re never gonna work again, and their life becomes this endless check to check lifestyle where they’re stressing out about that stuff.

Yeah, you’ll find these dudes who are well into their thirties and still pushing demos thinking they’re gonna blow up.

There’s tons of weird stigmas like that. I’m fuckin’ 34 now, I turn 35 next week. I remember when I was younger, I read that Jay-Z was 33 and I was just like, “Damn! This dudes really still goin for it?” It’s just so rare that you see any rapper over 30 doing anything interesting. But now, I’m just here and at this point, this is all I like doing.

Why do you think that age cut off exists in hip-hop? It seems like in other genres, artists have no problem recording into older age and keeping a following.

Yeah, no one’s really gracefully aged. I guess you’ve got Ghostface or a guy like Doom [who have], but I don’t know. A lot of it is just the attitude of the person and the way they approach what they’re doing. I’m finding I’m more into it than I ever have been. I’m less into the scene and less into knowing about what the fuck is new and cool, but I’m still very much there in my head and going for it. Maybe that’s allowed me to focus on the actual song making. I always wonder when people fall off, I’m like, “Do you think that guy knows he fell off? Or does he just think that he’s doing what he’s always done?” I feel like I would know if I sucked. I don’t think I’ve declined on a skill level, I don’t feel like slowing down. If people are into what I do then I’m still doing it. I’m just making songs over here. So, whoever wants ‘em.

Are You Gonna Eat That? is out now on Rhymesayers.