The first thing you need to know is this: my sleep habits for most of the year 2000 were atrocious. There was a point where I thought four hours, or four and a half, could sustain me. And so I’d be up late, sitting online and messaging with friends into and past the small hours, hoping I wouldn’t see the first traces of dawn lighting up the sky before I fell into sleep, before my alarms rung me awake to go to a job in Midtown. I’d be up at eight-thirty and in to work by ten, and I had no idea what I was doing: sometimes sad, sometimes frustrated, hesitant where I shouldn’t have been, inarticulate when I most needed words.

How this factors into things is that some of my friends started getting together at a bar in the East Village on Friday nights. The bar was called Old Devil Moon–it’s not there anymore; the last time I was in there was in or around 2008, and that was the first time I’d been there in years–and they had a bluegrass night on Friday nights. I rarely made it out to the bluegrass night because generally my Friday nights involved me falling asleep on my couch at around eight o’clock and never entirely putting two and two together and connecting this up with the overall lack of sleep I’d gotten earlier in of the week. And I so I missed getting to see abundant bluegrass at a small bar and restaurant in the East Village where bands played in one corner and a model train would sometimes run overhead.

There was a group that played there pretty frequently called Jim and Jennie and the Pine Barons. (This would later become Jim and Jennie and the Pinetops; they released a couple of albums over the years, most recently in 2005, and toured with Neko Case.) And, based on the one time I saw them there, they were a hell of a lot of fun: great vocal harmonies and plenty of energy and the ability to play an irreverent song one minute and a somber and haunting one the next. They were a band that stuck with you; they were a band you remembered, that you find yourself writing about when you’re drinking coffee late at night and heading rain fall slowly outside.

Early in 2002, I was sent a review copy of Didn’t It Rain, a new album from the group Songs:Ohia. I’d followed the band for a while; had seen them play a show at Brownies a couple of years before, had interviewed Jason Molina for the zine that I’d done in the 90s. I don’t remember if I first picked it up from looking at the album credits or if I realized it from listening to the album, but either way: the bluegrass group I’d heard on my friends talk about, that I’d seen on a couple of nights in East Village or elsewhere, was on there. And so you had Jason Molina’s voice, perfectly wounded, already weary, never not hopeful, and then you had these ethereal harmonies behind him. A kind of cathedral that surrounded him and slowly fell away.

There are eight songs on this album. On the first one, the title track, Molina sings, “We’ve got to watch our own backs.” By the end, this will have been disproven. There aren’t many albums I would consider perfect, but this is one of them. I’ve been listening to this album regularly now for over a decade. But it’s also not an album that you can listen to all that regularly; when I suggested that a friend listen to it, he did, then asked me if everything was okay. And with a little more remove, I get it: it’s an album that evokes depression in a more expressionistic way than most.

But right now, I’m talking around it. Because, yes, you go through seven pretty much perfect songs and you get to “Blue Chicago Moon,” close to seven minutes in length, and you listen to a guitar’s notes hang in midair, and eventually the drums come in, and there’s a valedictory flourish; this one’s the summation of everything that came up to it. Molina’s singing with a fullness he didn’t have before, and if the band doesn’t swing, they at least crackle; this is building up to something. You can hear it; call out the studio name: Electrical Audio. Listen to Jennie Benford singing wordlessly while Molina chants out a lament, the words “Space is loneliness,” over and over.

But I’m still not getting at it. There’s a structure to this song; there’s not quite a chorus; there’s just those two voices and the crescendo, run through variations. And I’m mostly talking around it now, because what happens a little over halfway through the song is a moment that haunts me most every time I hear it. He sings about the blues being your hunter, and he sings about coming “face to face with the darkness and desolation.” And then Jason Molina sings the word “Endless.” And he repeats it, and repeats it, and repeats it. And when you listen to that album, alone in the dark–maybe you’re in your office, you’re in a car, you’re in a venue when someone’s cued up this album to play between bands–you can’t not listen to it. You can’t reduce it to something ambient. This is a work that demands you.

And so I listen to Jason Molina singing the word “Endless” over and over, and each time, each repetition, I wonder what the next word to come will be. And I wonder if, at some point, no word will come that isn’t the word “endless,” that this will be where it goes, that there won’t be a way out, that there will only be that loop, that endless “endless,” that joke played on all of us.

The word that follows “endless” is “depression,” and it might be the only time when hearing this word comes as a relief, not for what it means, but for the fact that it signals a change, a progression, a step out of the stagnation. And eventually, catharsis does come. We see the light coming towards us. We hear the words “You are not helpless,” and it’s one of the few times I’ve heard that sentiment sung in a song when it felt earned, when it read like a statement someone had fought for.

The last words Jason Molina sings on this album are, “I’ll help you try to beat it.” And that’s the answer, that’s the refutation of the words he’d sung earlier, about us having to watch our own backs.

This is a song that haunts me on an album that haunts me. I think of wanting to listening to bluegrass in 2000 and not quite being able to outsmart certain bad impulses. I think of listening to this album for the first time in 2002, working at a terrible job that I couldn’t quite figure out how to quit, and seeing that maybe, just maybe, this resonated with me in ways that I hadn’t put together. I listen to it now, but I don’t listen to it too much, for fear that whatever hold it has on me will go away, that I will allow it to become ambient, and that’s not something I can bear.

This is a song that will never not help me breathe, and this is a song that will never not break my heart.

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