Clint Michigan. Photo by Allison Michael Orenstein

Clint Asay has a chipper demeanor, as you’d expect from a former cocktail waiter at Sidewalk Cafe and bartender at Metropolitan. But he also records heart-heavy, semi-biographical folk as Clint Michigan, which is why I recently found him telling me, with a self-deprecating laugh, “I don’t want anyone to feel sorry for me.”

Centuries, Clint Michigan’s second album for Kiam Records and first proper record in nine years, revisits a very specific segment of Asay’s history, when a struggle to stay clean stalled his creativity. The album’s very existence is a victory against those roadblocks, even if he doesn’t believe they’re entirely behind him: he cites his unwavering perfectionism in the studio, minor bouts of stage fright and, at one point, questions the idea of calling himself a musician, believing he lacks some virtuoso quality all artists must possess. But Centuries fashions a success for itself on two of Asay’s foundational strengths as a songmaker: the clarity of his bleak lyrical reveries and his arrangement of collaborators, which includes members of Julie Ruin and The Moldy Peaches.

Ahead of his album release show at Union Pool on April 29, Asay spoke to Bedford + Bowery about his roots in comedy music, his friendship with Quelle Chris, and walking the fine line between writing honest songs and self-obsession.

BB_Q(1)What has your rhythm for writing been like in the time between your first album Hawthorne to Hennepin and Centuries?

BB_A(1)I actually had another record that I self-released called Coeur d’Alene, but it was very difficult. It wasn’t fully finished, but I put it out anyway. I’ve been recording this one for five years, though.

This album took five years to make? Why was that?BB_Q(1)

BB_A(1)Well, because I didn’t have all the songs [laughs]. I like recording; if I could just record forever, that [would be] my preference. In fact, a lot of these were written while recording. I guess it’s also so personal that part of me didn’t want to put it out, you know what I mean? It’s more therapeutic for me to record it, and then when I get to the point where I have to release it… [laughs] it’s a relief.

BB_Q(1)When did you write the album’s last song, “That is All, That is It”? What led you there?

BB_A(1)My first and second records were recorded by a friend of mine named Jim Bentley. He owned a studio in Bushwick called The Fort, and he ended up killing himself. I was really upset, but at the same time you’re pissed off, you know what I mean? I had to write something, because he was the person I’d always made music with.

I didn’t realize at the time that he was producing my records, so then when I went and started working [on Centuries], I had to make all the decisions. It was really on me to make this record without a lot of feedback.

BB_Q(1)Being a studio musician can put you in a difficult spot, it seems: feeling like you’ve said everything you wanted to through the songs, but then are put in situations where people are asking, “What’s this line mean?” etc.

BB_A(1)There is a lot of personal stuff going on in the record, but then there are [songs] about other people. I had a moment where I was kind of out of control. [This album] is about knowing that everything is difficult and people are just trying to do the same thing — survive — regardless of which avenue you take, whether it be through drugs or something else. I feel like I’m being really honest [with these songs] and I don’t think it’s in a pitying way. When I write, I’m really careful to also make sure it’s listenable. There’s a fine line between honest songwriting and being really cheesy and self-obsessed.

BB_Q(1)Do the people that know you personally expect your music to have a bit of humor or irony in it?

BB_A(1)Well, I started out doing comedy music, in the early 2000s. I was in a comedy band. It was easier and less vulnerable to write songs with my old band. Then I started playing at the Sidewalk Café, where the anti-folk scene was. Regina Spektor, Nellie McKay and Kimya Dawson were playing down there, as was Toby Goodshank, who sings on “Shirt Off,” was singing there, so we’ve been friends for a long time.

I was the cocktail waiter there, and I saw some of the open mic stuff and I was like, “I could do that.” So I bought a guitar and started writing comedy songs with my friend Ben, but I think I always wanted an outlet to play more serious stuff. Jennifer O’Connor, who owns the label, and I bartended at a gay bar over here called Metropolitan where she gave me a copy of her album The Color and the Light. I didn’t know what to think, but I listened to it and it was so moving and honest. We became really close and she was an encouragement to writing more earnest songs. And I’ve always liked really depressing music [laughs].

BB_Q(1)Rapper Quelle Chris animated your video for “Shirt Off.” It seems like a very unexpected collaboration; how long have you known him?

BB_A(1)I was doing the door at Union Hall for comedy shows and met his fiancée, Jean Grae. I just loved them and so we became friends. I don’t like being in videos and I knew he did a lot of cool stuff with Jean’s show, so I wrote Quelle and asked him, “Do you know any animators?” and he said, “Well, you know Clint, I’ve been animating since I was a teenager.” I didn’t even think he would make it — he’s always busy making shit — but he understood exactly my idea and he added so many new ideas, like when [the boy in the video] reaches out and pulls that heart into the shirt. He understood the physical manifestation of the shirt was about feeling restricted and hiding.

BB_Q(1)Now that you’ve completed this long-gestating record, do you feel like there’s not like a fire in your belly to put out another record?

BB_A(1)No, no! [laughs] Now what I want to do is book some more shows. This is motivating me to finally learn from the kids, maybe get some pedals and like experiment with sound while being able to play without, like, this huge band.

I don’t even know if I consider myself a musician. I mean, I write songs, but I remember I used to be so embarrassed carrying my guitar to rehearsal because people would be like, “Are you a musician?” and I’d be like, “Uh-uh, no, I’m just bringing someone their guitar!” [laughs]. I just didn’t want other people to think I thought I was the shit.

Correction: Due to an editing error, the original version of this story misspelled Julie Ruin in the headline.