Part of what made New York-raised country singer Dougie Poole’s 2020 album The Freelancer’s Blues so appealing was its piercing self-awareness. Poole, now based in Maine, is clearly a gifted songwriter with a deep enough understanding of country music to feel comfortable dismantling some of its structures as he goes along. But the album really broke through because Poole was writing about the millennial routine, the type of thing that would have been cringe-worthy if it hadn’t been so wryly funny and so carefully crafted.

It was affecting, too. Tracks like “Vaping on the Job,” “Buddhist for a Couple Days,” and the “These Drugs Aren’t Working” did capture something essential about the apathy and exhaustion of being alive right now. There was a deep-blue despair to “Los Angeles,” a song about that all-too-familiar New York thing where you tell yourself and all your friends that you’re moving to California, where you’ll finally be happy, before scrapping it all and re-upping your lease in Brooklyn. It wasn’t really about moving to California; it was about fantasy and self-sabotage and that odd feeling of fighting yourself and losing.

On his latest single, “High School Gym,” Poole unmoors himself entirely from the day-to-day. Here he explores grief, dreaming of gathering everyone he’s lost together in one since-demolished building. “When somebody that you love dies, they might visit you in your dreams,” Poole said in a statement alongside the single’s release. “They can ask you things or tell you things. The conversations continue and feel perfectly real. Little gifts your brain can give itself.” There’s more than a little Springsteen to the whole thing, the understated grandeur of his delivery, the looping drums and synths, the melancholy that never slips into sentimentality. Poole always had this poignancy lurking beneath his best songs, but he might be at his best when he’s bringing it to the surface.