Jeremy Messersmith’s latest album Late Stage Capitalism is his first album with his face on it. It features a portrait of Messersmith backed by pastels, goggles over his eyes. Previous album covers have illustrations or abstracted, colorful fractals, but this one shows the visage of the artist, front and center.

“I kind of wanted to put myself on it — like this was not normally a thing I would ever do. … I wanted it to look kind of like I’m a product and I’m literally selling myself,” Messersmith said.

Late Stage Capitalism, which was released earlier this year, is an 11-track collage of songs spanning subjects from Jim Bakker the televangelist to Cleveland the city, all of which touch on the theme indicated by the album’s title and are married by a strand of nostalgic musical influences.

“I kind of just wanted to go to my musical happy place with the record. I wanted to do something that sounded like music from the ‘50s, ‘60s, ‘70s, music like that era. … Because for whatever reason, I’m wired to really, really love it. It’s physically fun, joyful, pleasurable to play that kind of stuff,” Messersmith said.

He described creating the album as a “sonic playground” and counts Cat Stevens, Françoise Hardy and Emitt Rhodes amongst its influences. “It’s nice to dial into a sonic palette. It’s fun to build a little sandbox,” Messersmith said.

Late Stage Capitalism is Messersmith’s most expansive work instrumentally, with soaring trumpets and organs tucked in between the more prominent percussive elements and guitar. The album also maintains Messersmith’s well-honed style of lovingly detailed lyrics, which, in general, are intricate, building small but detailed landscapes.

“The thing with songwriting, is you don’t have a whole lot of real estate with which to do worldbuilding really, so it helps if you’re super specific and kind of let the listeners’ brain render the rest of it with their own information,” Messersmith said.

“Fast Times in Minnesota” off of Late Stage Capitalism enacts this sentiment around place, touching on various locales of the Upper Midwest and tying in its regionalisms: “He’s never comin’ back / Fast times in Minnesota / Just east of South Dakota / Uff-dahs and, yeah, you betchas.” It’s a homey homage, grounding the song in a specific sort of Americana.

“I guess if I want there to be a very specific thing (in a song), I’ll try to be specific about place. I tried very hard to work in a bunch of regional things,” Messersmith said. He also added that the song does “very well” in Minnesota, as opposed to other audiences.

Minnesota, where Messersmith is based, also holds a special place in his musical foundations and inspirations and often appears as that rooted place in his lyrics.

“When I moved to Minnesota, it turned me into who I am, not just musically, but who I am socially, politically. … It was where I was able to find myself in the way that you do when you’re in your early 20s,” Messersmith said.

Though Late Stage Capitalism was released last March, Messersmith actually wrote the album about three years ago, initially conceptualizing it as a “very fun, loose critique of late-stage capitalism.” After the presidential election of 2016, however, the album took on a new, more dire tone. Messersmith described it as a “pre-Trumpian artifact,” as most of the songs were actually written and recorded about three years ago. He then decided to put the album on hold and pursue another project in the interim, which became 11 Obscenely Optimistic Songs For Ukulele: A Micro Folk Record For The 21st Century And Beyond, released in 2017.

“I feel like that (time) was a landslide as far as media landscape and what people should write about,” Messersmith said. “I thought, maybe people would need it, but, most of all, I needed it. I really had to strip away a lot and try to write things very simply. I was just kind of reeling with what I believe, what are my core things, what I’d like to share.”

The album that resulted is a resoundingly positive and ironically enumerated 10 songs about peace, love and a steadfast belief in the bright future ahead, all balanced with the simple chords of the ukulele.

Though most songs on 11 Obscenely Optimistic Songs are under two minutes in length, each crystallizes a singular, “obscenely optimistic” thought — refracting into a vignette of positive thinking. “Everybody Gets a Kitten,” the first song on the album, for example, quickly creates a vision of a future in which everyone does just what the title suggests.

11 Obscenely Optimistic Songs was released in the form of a songbook in addition to an album, allowing for people to easily play along to the chords and lyrics — which resulted in a pantheon of YouTube-uploaded covers, each with their own flare. Messersmith learned to play ukulele specifically for this project, and its egalitarian nature was something Messersmith kept in mind with its release.

“To me, it fits the definition of maybe the purest folk instrument. Like a very humble instrument, that’s not fancy,” Messersmith said. “I wanted people to play the songs and sing them on their own.”