Boone Howard’s charm is a blend of his misfit stage persona and his musical talents. Never has this magnetism sounded so gloriously despondent as on his new LP, The Other Side of Town.

Howard’s who’s-who ensemble of Portland ringers (members of the Domestics, Hustle and Drone, Howard’s former band the We Shared Milk, and Minden) conspire to transcend the confines of dark indie-pop and move into something headier. Lurking within the album’s gloomy vibes, the hypnotic opening track “Satan” owes inspiration to OK Computer atmospherics. Howard sings the phrase “You’re not gonna leave a mark” in what’s perhaps a moment of false bravado, considering the record’s subject matter is largely centered around the fizzling of a romantic relationship.

He confronts patterns of self-abuse on the dreamy “Wouldn’t Believe It,” with swirling feedback approximating the confusion of a post-rager dawn. “Half a Life” is disguised as a piano-led tear-jerker, but also features Howard’s smarmy lyrics and tough-living croon. Later, the ’70s rock murmur of “I Don’t Even Know What It Is” explores the deep misunderstanding of the proverbial “it” with emotional non sequiturs over murky pop. He sounds like a red-eyed Julian Casablancas roaming an empty room and singing to himself. It’s satisfying, despite the song’s inherent aimlessness.

Howard’s theatrical unpredictability in a live setting is measured in self-afflicted microphone hits to his head and dramatic collapses to his knees. Though sometimes lewd, his lyrics and tender delivery contradict everything you’re expecting. This symbiosis between the two Howards—one a lovesick balladeer and the other an alleyway street poet—is portrayed dutifully throughout The Other Side of Town.

The album’s triumphant finale, “Staring at the Sun,” offers a full-bodied aural onslaught from Howard and his band of merry pranksters. Warm organs, splashy drums, and wild yelps crash into each other like a great explosion of rock ’n’ roll bombast. It’s a thrilling bookend to an album pocked by so many psychological crags.