We drive toward downtown, where Longstreth’s older brother Jake keeps a painting studio. We talk about The Blues Brothers joining the canon of flinty, ’70s American cinema, and how Magic Eye illusions double as a metaphor for the concentrated power of female orgasm. Longstreth’s music is tightly controlled, anal, even, and yet his conversation has the constellatory sprawl of someone who just figured it all out with five minutes left on their phone battery. You get the sense that his composure is a project unto itself.

We get off the highway and stop for coffee, which Longstreth identifies as a “vice.” One of the baristas looks conspiratorially at Longstreth as though he recognizes him from the internet, which could be: The video for “Keep Your Name” is almost nothing but Longstreth’s face.

We drive the last few blocks to Jake’s and park. Longstreth fields a flurry of text messages about whether or not he’ll be able to use a Tesla for a video shoot later in the week, for a duet with the singer Dawn Richard called “Cool Your Heart.” Longstreth’s idea is to have him and Richard breaking down in a Tesla somewhere in the woods, which the Tesla company is apparently not keen on, and now everyone involved is in some state of tripping. Everyone except Longstreth, at least, who seems to succeed in part by coupling genuine politeness with unbending will. It can’t, he explains, be a “1998 Accord or a 2017 Lambo.” It can’t be a “murdered-out Camaro.” It has to be a Tesla.

Jake’s studio is on the second floor of a warehouse he shares with several other artists. The room is bright and open and a little messy, a place where things are done by hand. Jake, a plainspoken, unpretentious guy who considers himself the weak link in a Grateful Dead cover band, gives me an impromptu tour of his work. The primary subject is what he calls “American corporate architecture”: big-box stores and chain restaurants stripped of their brand names and rendered in the neutral tones of palliative care. There are no people in the paintings, and the buildings themselves end abruptly in desert and wilderness, demarcating the edge of civilization. They are beautiful and stark and seem to be painted from a lonely place in the near future in which we realize we have made a colossal mistake.

The Longstreths grew up in Southbury, Connecticut, a town near New Haven they say is known primarily for its retirement community. Their father managed a nature center for the Audubon Society and their mother was an attorney for the state. As teenagers they started a band called American People, and Jake realized Dave was freakishly talented. (As an older brother, you understand, these admissions aren’t easy to make.) Jake went off to a small college in Portland, Oregon, while Dave ended up at Yale, near home.

School made Dave miserable, so he dropped out, joining Jake in Portland and falling in with an indie-rock scene that stressed democracy, self-reliance, and the endangered notion that amateurs have as much right to art as so-called experts do. Longstreth eventually went back to school in part because of the strain dropping out had put on his relationship with his parents, but the liberation of Portland had flipped a switch.

Longstreth’s singularity and determination can make him seem like an unlikely younger brother. But in his own way, he seems to have been following Jake. Later, when I ask Longstreth if he had an epiphany about leaving New York—a flash of lightning in a field, an eagle landing on a cactus—he says no, not exactly. Still, he remembers the conversation with his brother. “Of course,” Jake had said. “That’s the only move. I’m glad you came to that conclusion, but I knew that a long time ago.”