Consider the notion that happiness is a sad song.

There is a theory of melancholy for each of us. The modern poetics of sadness and depression—that awesome, airless gap between what we are and what we dream (or dread)—carries an exclusive, more personal sting than most other late philosophies. Gaston Bachelard and Walter Benjamin, two writers obsessed with melancholy, focused on our smallest personal perceptions as a partial theory of understanding this obsession. Human life is a succession of spaces and objects, never clearly seen but for our sad, unconscious scribbling over them with memories and desire. Bits of experience, real and imagined, stick in perception. Thus each of us authors our own theories of dolour and disconsolation, dreaming, longing, the blues.

This is why Ayn Rand’s worldview always felt, to me, like a bill of sale. Her vision of super-selves was fine to inspire, but less than fine when it trashed the melancholic as delusional, weak, a thing that must be disposed of as the price of living like a god. By droning on about the superhuman, about titans like Dominique and Roark, she revealed how stone-blind she was to much of what constitutes human essence, the authentic soul in all its flaws, and how deaf she was to the music of what gives shape and dignity to our small, lonely defeats. Rand was a fraud, and miserably lonely besides. (And superwoman or not, I could have easily kicked her ass in a fight.) I begin discussion of a band and an album in this manner because of how highly individual the blues is, and because in order to deeply understand one’s own aesthetics, even the aesthetics of love, one could do worse than to contemplate a personal theory of the melancholic.

I was asked once what song makes me burst into tears every time I hear it. This was a loaded question; it did not miss its mark. More than the usual amount of self-consciousness kept me (as it might keep anyone) from being honest at the moment of inventory, and I think I mumbled something quiet and dignified by Nina Simone, which was a lie. Nina Simone has never made me sad, never made me safe and dreaming inside that sadness. I listen to her with great love, but few tears. On the other hand, “Easy From Now On” by Emmylou Harris, Keith Jarrett’s solo version of “Shenandoah,” even Paul Simon’s “Graceland,” when the male chorus throws up that wall of minor chords behind the lyric: losing love is like a window in your heart—oh, yes. Along with hundreds of small, barely noticed turns of phrase in random songs I’ve heard since the beginnings of sentience are artists whose works deliberately incarnate a more visceral feeling and manage to pull it off, at least with the right pair of ears. When listening to them, we might sense they’ve helped to construct our own multi-layered sadness and, in so doing, have constructed an exit, a way through it. This is part of a personal theory of melancholy. Gillian Welch. Ennio Morricone. Mark Hollis and Talk Talk. Oh mais oui.

But few albums bear the grandly melancholic so well as an obscure thirty-nine-minute wash of pop and percussion known as Hats, a 1989 release by the Glasgow trio The Blue Nile. Today this work maintains a cult love and devotion (like all albums that sell no copies—such is the self-flattery of the cult fan). This love is made all the more poignant by my personal belief that Hats is the least hip recording in the history of pop music; it is sentimental and bleak and untimely and has never, ever been imitated. If I recall correctly, upon its release critics responded to the album’s unusual scope and sound with language that fumbled and stuttered to locate visceral descriptions more cinematic and atmospheric than musical, only to devolve at last into the unavoidably personal, just like the Blue Nile itself. Reviews became confessionals, self-therapies, sad-sack letters that could have been addressed to Miss Lonelyhearts. Hats was the sound of worn clichés—hearts breaking, falling in love—sung for those who dream in colour and stupidly believe in love, believe in its strange provenance and understand it as unequal parts damage and healing, contradictions breathed into the same body. The album was gorgeous and sad and inspired a fear I’ve never seen seriously attached to any other work of art, musical or otherwise. There in the accolades lurked a dread of having to share Hats with anyone; reactions were too sharp, too strong, too easily disbelieved and dismissed as nothing but worship born of ennui, unbalanced love, lunacy.

Singer and principal songwriter Paul Buchanan, in 1989: “I just hope that people get new things out of the music, things they don’t get elsewhere. Like you get new things out of dreams.”

Hats was a dream and a new thing. It’s difficult to imagine someone hearing the album for the first time now, fifteen years after it came into being. Much of what defines the silly, cacophonous sound of the eighties—thin, echoing snare drums; processed bass; distant “classy” horns; orchestra strings that sound as if they were recorded in an auditorium made of tin—was muted and transformed on Hats to sound like a necessary screen between instrument and performer, emotion and listener. In this way the album is a conduit, just like the happiest sad songs. To believe that art is a conduit to memory or dream is part of melancholic theory. As an example, in the house where I grew up there hung a painting—I do not know the painter—of a darkened street, in thick oils with washes of murk and gray, meant to suggest streetlamps in the fog after a long rain, and bits of blue receding like a broken stone path to a vanishing point. There seemed to be rain falling at an angle, inside and across the grey lights. There was a dollop of red in the middle left that looked like an awning on a Parisian café. None of this imagery was painted so much as implied, as if the paint knew itself to be only a medium. This painting, which is lost to history, appears whenever I see the words “city street” together on a page. The first time I arrived in New York, that painting superimposed itself over the city at night, floating into position at the sound of a taxi leaving, of traffic across the river, of a stereo playing the Blue Nile. A painting conflated with a band. Now I’m helpless to imagine New York without the cinematic language provided by Hats. I did not ask for the association, but the album is for me the permanent sound of urbanity, which is the sound of self-isolation, of pure loneliness in the face of something so dark, so great.

How to describe it? Hats is of this twilight world, with lingering images of headlights, streetlights, miles to go before sleep. The unvarying instrumentation of drums, bass and strings repeats to the point of hypnosis and locks onto Buchanan, whose glorious untrained voice manages to remind me of Nina Simone . . . he sounds nothing like Nina Simone, I realize. (In fact, when he’s worked up about lost love, Buchanan sounds like a Member of Parliament.) But Buchanan’s voice is the center of the Blue Nile, the heat the band gathers around, and his gift for hugging melody to lyric is as ragged and inspired as the woman who sang “I Put A Spell On You.” Before the first chorus of “The Downtown Lights”—track two—Buchanan’s voice, at full volume, breaks on the lyric nobody loves you . . . tumbling downward with each word to land soundlessly on . . . this way. And like the most deliberate pop singers (those who feel their way through phrasing), Buchanan is able to rip untapped power from the simplest, most sentimental lyrics, all the while understanding the threat—as I’ve said before, the true advantage of singing inside pop structures—of insufficiency.

Each time I fall for you it hurts me a little bit more
than I want it to . . .

Tomorrow I will be there
oh you wait and see

An ordinary girl
can make the world all right

Again, how to describe it? It is forty minutes in the dark of night, with lyrics like this, sung like you can’t imagine—until you hear them. To place the sound of the Blue Nile in some historical context: critics can argue about which album gave spiritual birth to the 1990s (Achtung Baby, Kiko, Nothing’s Shocking), with that long decade’s relentless marketing, gleeful posturing, acute self-awareness, ironic fucking of genres and post-celebrity divertissement. But the little album called Hats could officially be named the Last Album of the 1980s, the sound of ten gilded years closing the door on themselves. It was intended, as Buchanan warned upon its release, to be an album two adults took with them into a shuttered room, as if the miserable 1980s were something that needed to be survived and regretted, a long, loud celebration that demanded an adult appear at its close and call it a night.

How to describe it? It is Hats. The band is the Blue Nile. They have existed for over twenty years, but have released only three works to the public (Hats is their second album), totalling less than three hours of music.

I mentioned the word “lunacy” before. Melancholic beauty has a certain lunacy to it, if only in the sense that we are very much alone as we experience it, lost inside perception, helpless to persuade another human being of its source—but because of that helplessness I believe there’s an album of this lunatic sort for each of us. It’s an album very like a novel, one of those novels, the few you hesitate to press on friends for fear they will prove unworthy of your friendship. And for fear that you have disclosed too much of yourself, let something slip which you should at all costs keep private. A private, broken love is always more interesting than perfect love. We dislike perfect love, and dislike hearing about it. But miserable love? We require a work of art to speak to this, to contain the misery, perhaps leaven it—at the very least to preserve it for some reason as part of memory and desire, thus remaining a reliable connecting point for that desire. Andrew Solomon once wrote that “depression is the flaw in love.” I do not want to debase clinical depression by throwing that word around when I mean something far less crippling. But for the common sadness of daily—not to mention nightly—living, there is a language of flaws, cracks, bits of experience that stick in perception. Art is among those flaws. If you don’t believe me, investigate what your imagination calls up as random associations the very next time you find yourself staring into familiar landscapes. That picture? That sound? Welcome to your own theory of the melancholic. You are not alone.

Paul Winner unfurls the Score every second Monday.