The only album Kenny Knight ever released is about American Sadness: the especially poignant, timid melancholy of a people who are raised up to believe their dreams are destined to come true, the cold desolation that settles in when they don’t. Crossroads stares down the barrel of the ’80s, riding high on fumes of free love and a peaceful, easy feeling. Sure, Knight coasts and moans like Don Henley or Joe Walsh, but his gentleness is more essential to the record’s overall feel. Jim Croce and Jackson Browne spring to mind as easy contemporaries even if Knight leans harder on the country canon than either of them did. These are cowboy lullabies with their outlaw instincts replaced by middle class ennui, and they are phenomenal.

Each song on Crossroads sounds like it could spawn its own album, which is bound to happen when a songwriter of this generous, prolific nature is confined to releasing only one record. “All The Memories” is a Nashville Skyline track stripped for parts and reassembled as a song of mourning. “To Be Free” starts like a spoken word incantation, the inner monologue of an elderly, bedridden invalid, then turns into a windswept journey through the wilderness, psychedelia pricking up its ears at the tail end. What startles me most about that one is the empathy of spirit it takes to imagine the longings of a rocking-chair-bound senior citizen. Not only does Knight imagine those thoughts, but he deftly shapes them into a late-life-rallying cry. The way the song switches between two rhythms mirrors its narrator’s slow, sad reality and the fantasy life he longs for, a fantastic structural reinforcement of its theme.

There’s pain of all sorts on this record, whether imagined or biographical. Some breakup songs are so brutal they sour you back into your own grief — “Jean” is one. It seems to swipe through the scenarios of waking up to a stranger, to a tired, worn-out lover, to no one; it’s a muttered murmur at a fading figure who is leaving in a wake of confusion and betrayal. “Carry Me Down” chugs along on cowboy piquancy, Knight doling out his phrasing in pockets and short bursts like this isn’t a song about getting dragged to the brink of your own grave. It fades in like a radio dial got turned up, reinforcing the feeling that this is a song my grandpa would’ve put on for the long drive home as I sat jostled in the middle seat of his pickup truck.

Crossroads is the railroad blues as told by someone who couldn’t make it out of Denver, and the reissue of this 1980s gem by Paradise Of Bachelors doesn’t just feel timely, it feels necessary. This is a lost and undervalued part of America’s history that is quickly fading. Since we’ve got 20/20 hindsight, I can almost hear the ominous onset of industrialism and technology lurking as the country went careening toward the boom and bust of the ’80s. These sounds disappeared soon after: the earnest flute of “You Can Tell Me I’m Wrong” and the black tar rebellion of “Baby’s Back,” or the weird, wide-eyed paranoia of “Whiskey.” Whether Knight knew it or not, his album title was a prophetic description of American history — the nation was certainly at a crossroads. Listening to this unearthed bit of our past hammers that point home, so stream it below.

Crossroads is out 5/12 on Paradise Of Bachelors. Pre-order it here.