From left: Gillian Lisée, Seth Vanek (seated), Kent Lambert, and Sam Wagster Credit: Courtesy Roommate's Facebook page

Before I meet Kent Lambert for the first time, he e-mails me a song he recorded and released in 2001. It’s called “RP (Forget the Metaphors),” and it saw some airplay on Belgian national radio in 2002. Audience members still requested it this year when he played a monthlong residency at the Hideout with a rotating lineup of bandmates. When we meet up and drink beers in the Ukrainian Village, Lambert tells me how it’s the song that motivated him to keep making music as Roommate, the project for which he’s collected his various musical impulses during the past decade and a half.

Roommate began around the turn of the millennium in New York City. Lambert worked for an independent film distributor at the time, and he had a roommate who acted as a “life coach,” he says. “I would tinker with things obsessively and never finish them. He’d give me assignments when he’d leave town for the weekend, like, ‘You should try to record a whole song.'” He honored his roommate’s assignments, and then he acknowledged the significance of that encouragement by naming the project after him.

Though it’s the song he sends me before we meet, “RP” isn’t the best example of the kind of music Lambert currently makes with Roommate; it’s a solo-piano number with narrative-driven lyrics (the “RP” stands for “River Phoenix”) that deal with his celebrity and death, sounding like a slow love song to a ghost. If there are ghosts on Roommate’s new album—Make Like, released in June on Strange Weather—Lambert never addresses them by name. His new lyrics are free-associative and darkly playful, cast against a fevered backdrop of psychedelic art-pop.

“I had a lot of anxiety about being the guy at the piano who likes to sing stories about things that are happening in his life,” says Lambert. “So I got interested in wordplay, drawing from hip-hop in terms of internal rhymes, but still getting at some of the same concerns.”

Those concerns—celebrity, escapism, power, suffering, alienation—now manifest in abstract language and stray references. One song on Make Like stems from a phrase he thought of in a dream: “Secret Claw,” two words that when put together form something both menacing and nonreferential. Sometimes Lambert still lapses into second-person perspective and accusatory gestures. On “Snow Globe,” a highlight from Roommate’s 2011 album Guilty Rainbow, Lambert sings, “If you’re someone who cares a lot about the problems of the world / What do you say to the other boys and girls? / Do you try to play it cool? / Or do you dare ask if they care along with you?”

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Those questions are posed during the song’s musical climax, and they epitomize what makes Roommate distinctive. Lambert asks you to care about what he cares about without making eye contact, slipping his worries into a perspective where they can be interpreted as something else entirely. On Make Like‘s “Dancer Howl,” Lambert stacks up another stanza full of questions: “Do you still get chills when the kill screen fades? / Are you paragon or renegade? / Do you dare to want for better days?” If you’ve ever played Mass Effect, you’ll recognize “paragon” and “renegade” as the two branches of your character’s morality tree: be nice to supporting characters, and you’ll collect blue paragon points, while acting like a tough jerk lets you pile up the red ones. Both styles of playing have in-game advantages, though it’s strange to see your moral reputation quantified onscreen.

“I like to engage with culture,” Lambert says. “I want to have some awareness of . . . what are the things that are meaningful to people younger than me? I don’t want to be stuck on the canon of my generation. So I got a Playstation and I consulted some friends and started going to game sites, and just dove in. But I didn’t feel comfortable doing that purely as a consumptive thing, so I got a capture device and I started wandering around in video game worlds and collecting imagery. I was also letting in new ideas about structuring a story. That convention of paragon or renegade . . . it happens in other games. That binary I found very amusing.”

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In his music and in conversation, Lambert fixates on the ways people distill complicated human experiences into absolute binaries. He works for the art department at the University of Chicago now, renting out video equipment and training students on how to use it, and he’s keenly aware of the poverty lines that surround the school’s south-side campus.

“I think that I have worked out the thickest, most pernicious anxieties through this process,” Lambert says of his songwriting. “Whether it’s things that are going on in the news or in communities surrounding me—things that are bothersome—this has been a vehicle for it: turning them into phrases and melodies and songs. Songs that are enjoyable to play and seem to bring other people enjoyment. That’s been a way of working through things that maybe otherwise I would have less healthy outlets for.”

Roommate isn’t an outlet of escape for Lambert—it’s a way for him to process experiences that often get codified into black-and-white talking points. He wants to see the shades in between the extremes. “I don’t want to tell people how to feel or how to think about these things, but I am trying to filter for myself things that might be horrifying or disturbing, that I might feel rage or anxiety about, and turn them into something that can be a meaningful experience,” he says. “We all are sharing in this culture and we all have our part in it. I don’t want to give myself an out.”