In 1974 a woman called Connie Converse got into her car, drove away, and was never heard from again. This was not noticed by the press. She was fifty and a failed musician, an eccentric and hermit-like woman who never caught her big break. But she left behind recordings of her songs—songs which, belatedly, have finally led to her getting a modicum of the recognition she deserved.

This is another of those stories of the misunderstood genius. Completely obscure during her career, she is nowadays recognized as a musician ahead of her time, one of the first practitioners of the so-called singer-songwriter genre. Her recordings remained unavailable to the public until 2004 when she was featured on WYNC’s “Spinning on Air.” Five years later, in 2009, an album of her homemade recordings was released—How Sad, How Lovely—which secured her place in the hearts of hipsters across Brooklyn.

In this essay I am, however, not primarily interested in analyzing her music. This is not because there isn’t much to discuss. Converse blends American popular styles—blues, folk, jazz, country—into a sophisticated personal style. Her songs are masterful on many levels: with piquant lyrics, sophisticated harmonies, and creative guitar arrangements. Deep originality, keen intelligence, and a fine literary sensibility make her posthumous album an excellent listen.

All this is beside the point. I want to use Converse’s music as the jumping-off point to discuss an essential question of aesthetics: Are there such things as aesthetic emotions?

In a previous essay on aesthetics, I tried to analyze the way that art alters our relation with the natural and cultural world. But I left unexamined the way that art changes our relationship with ourselves. For art does not only affect our stance towards our assumptions, habits, sensations, perceptions, and social conventions. Art also changes our relationship with our emotions.

The very title of Converse’s album invites us to consider aesthetic emotions: How Sad, How Lovely. She herself did not choose this title for the album; but it is well-chosen, since this feeling—the feeling of delightful melancholy—always comes over me when I listen to her music.

But how can sadness be beautiful? When tragedy actually befalls us—a career failure, a break up, a death—we are little disposed to find it beautiful. And long-term, grinding depression is perhaps even less lovely. Yet we so often find ourselves watching sad movies, reading depressing books, enjoying tragedies on stage, and listening to tearful ballads. Converse’s songs are full of heartbreak, yet many people enjoy them. We do our best to avoid sadness in life, but often seek it out in art. Why?

This leads me to think that the melancholic emotion we experience in sad art is not the same as “real” sadness. That is, when a beloved character dies in a novel we feel an entirely different emotion than when a friend passes away. Can that be true?

Perhaps, instead, it is just a question of degree: sadness in art affects us less than sadness in life. But this explanation does not do. For we do not enjoy even small amounts of sadness in real life; so why would we in art? And besides, anyone artistically sensitive knows that one can have intense reactions from art—quite as intense as any experience in life—so that it is clearly not a question of degree.

The explanation must be, then, that aesthetic sadness is categorically different from actual sadness. Yet we recognize an immediate and obvious affinity between the two feelings: otherwise we would not call them both “sad.” So it seems as if they are alike in one sense and yet different in another.

To pinpoint the difference, we must see if we can isolate the feeling of beauty. In novels, paintings, and songs, aesthetic reactions are hopelessly mixed up with a riot of other considerations: artistic intentions, subject-matter, moral judgments, and so forth. But when contemplating nature—in my experience, at least—the feeling of beauty stands out cold and pure.

In the forest of New Brunswick my family owns a property on a lake, where we go every summer to relax. Out there, far away from the light pollution of cities, the Milky Way appears in all its remarkable brilliance. Except for the ghostly calls of loons echoing across the lake, the woods are deathly still. Gazing up at the stars in the silence of the night I come closest to experiencing pure beauty.

Looking at the starry night I feel neither sad, nor happy, nor frightened, nor angry. The word that comes closest the feeling is “awe”: gaping wonder at the splendor of existence. I become entirely absorbed in my senses; everything except the beautiful object drops away. I am solely aware of the sensory details of this object, and perpetually amazed that such a thing could exist.

An important facet of this experience, I think, is disinterestedness. I want nothing from the beautiful object. I have no stake in its fate. Indeed, my absorption in it is so great that the feeling of distinction—of subject and object—dissolves, and I achieve a feeling of oneness with what I contemplate. Thus this feeling of disinterest extends to myself: I no longer have a stake in my own life, and I can accept with equanimity come what may. Beauty is, for this reason, associated in my mind with a feeling of profound calmness.

Using this observation, I believe we can see why sad art can be pleasant. My hypothesis is that the feeling of beauty—which brings with it a calming sense of disinterest—denatures normally painful emotions, rendering them relatively inert.

Real sadness involves the painful feeling of loss. To feel loss, you must feel interested, in the sense that you have a stake in what is happening. But experiencing sadness in the context of a work of art, while our aesthetic sense is activated, numbs us to this pain. We see sadness, rather, as a kind of floating, neutral observer in the scene; and this allows us to savor the poignant and touching experience of the sentiment without the drawbacks of emotional trauma.

And herein lies the therapeutic potential of art. For art allows us to see the beauty in normally painful emotions. By putting us into a disinterested state of mind, great art allows us to savor the sublime melancholy of life. We see that sadness is not just painful, but lovely. In this, too, consists art’s ability to help us achieve wisdom: to look upon life, not as a person wrapped up in his own troubles, but as a cloud watching from above.

Here I think it is useful to examine the difference between art and entertainment. In my first essay, I held that the differences is that art reconnects us to the world while entertainment lures us into fantasy. But the emotional distinction between art and entertainment cannot be described thus.

Rather, I think herein lies the difference: that art allows us to contemplate emotions disinterestedly, while entertainment provokes us to react empathetically. That is to say that, with entertainment, the difference between aesthetic emotions and everyday emotions is blurred. We react to an entertaining tale the same way we react to, say, our friend telling us a story.

Some observations lead me to this conclusion. One is that Shakespeare’s tragedies have never once brought me anywhere close to tears, while rather mediocre movies have had me bawling. Another is that drinking alcohol, being stressed, feeling sentimental, or being otherwise emotionally raw tend to make me more sensitive to blockbuster movies and pop music, and less sensitive to far greater works. Clearly, provoking strong emotions requires neither great sophistication in the work nor great appreciation in the audience; indeed, it requires a childlike innocence from both.

I believe the explanation for this is very simple. Crude art—or “entertainment” in my parlance—does not strongly activate our aesthetic sense, and thus our emotions are unfiltered. We feel none of the disinterest that the contemplation of beauty engenders, and so react in an unmediated naturalness. This makes entertainment the opposite of calming—rather, it can be very animating and distressing.

This may be the root of Plato’s and Aristotle’s ancient dispute about the role of poetry in society. Plato famously banished poets from his ideal republic, fearing poetry’s ability to disrupt social order and discompose men’s minds. Aristotle, on the other hand, thought that poetry could be cathartic, curing us of strong emotions and thus conducive to calmness and stability. In my scheme, entertainment is destabilizing and true art therapeutic. In other words, Plato should only have banished the entertainers.

This also leads to an observation about singer-songwriters. Unlike in other genres of music—musicals, operas, jazz—there is a pretense among singer-songwriters to be communicating directly with their audience; that their songs are honest and related to their daily lives. It is this intentional blurring of art and life that leads many fans to get absorbed in tabloid stories of celebrity personal lives.

I think this is almost inevitably a sort of illusion, and the “honest” self on display to the public is a sort of persona. But in any case this pretense serves the purposes of entertainment: If we think the musicians are giving us honest sentiments, we will react empathetically and not disinterestedly.

Connie Converse, on the other hand, creates no illusion of direct honesty. Her lyrics are literary, picturesque, and impersonal. This is not to say that her songs have nothing to do with her personality. Her preferred themes—unrequited love, most notably—obviously have some bearing on her life. And the sadness in her music must be related with the sorrow in her life, feeling isolated and unrecognized. But in her songs, the stuff of her life is sublimated into art—turned into an impersonal product that can be contemplated and appreciated without knowing anything about its maker.

I believe all true art is, in this sense, impersonal: its value does not depend on knowing or thinking anything about its maker. Art is not an extension of the artist’s personality, but has its own life. This is why I am against “confessional” art: art that pretends to be, or actually is, an unfiltered look into somebody’s life and feelings. Much of John Lennon’s work after the Beatles broke up falls into this category. By my definition, “confessional” art is always inevitably entertainment.

This is not to say that art must always scorn its maker’s life. The essays of Montaigne, for example, are deeply introspective, while being among the glories of western literature. But those essays are not simply the pouring forth of feelings or the airing of grievances. They transform Montaigne’s own experiences into an exploration of the human condition, and thus become genuine works of art.

In my previous essay I described how art can help us break out of the deadening effects of routine, thus revivifying the world. But art can also pull us from the opposite direction: from frenetic emotionality to a detached calmness. While contemplating beauty, we see the world, and even ourselves, as calm and sensitive observers, with fascination and delight. We rediscover the childlike richness of experience, while shunning the childlike tyranny of emotion. We can achieve equanimity, at least temporarily, by being reminded that beauty and sadness are not opposed, but are intimately intertwined.

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