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Not so long ago, when there were still record stores with album covers that were like small canvases of art, I used to occasionally ask those who worked there what they would identify as the saddest music they had ever heard. Keep in mind, this is the "album era".
Many went to the Classical world: the solemn slow layering adagios of Albinoni and Barber, the stark solitude of Beethoven's Moonlight Sonata, Chopin's Nocturnes, the Unanswered Question by Ives, Gorecki's Third.
I always noted the slight reluctance to choose Country songs, perhaps because they have so many superficial cliches for sadness, but I was often recommended to the plaintive "I'm So Lonesome, I Could Cry" of Hank Williams, George Jones' "He Stopped Loving Her Today," Patsy Cline's "I Fall to Pieces," Willie Nelson's "Blue Eyes Crying in the Rain" and, thankfully, the entire catalog of Townes Van Zandt.
Most of the time, the recommendations were from Pop and Rock music: a spectrum ranging around from Ray Charles' "Georgia," Sam Cooke's "A Change is Gonna Come," Roy Orbison's "Crying," Otis Redding's "I've Been Loving You Too Long" to Dylan's "If You See Her, Say Hello," Simon and Garfunkle's "Bridge Over Troubled Water," Gordon Lightfoot's "If You Could Read My Mind," the Jackson 5's "I'll Be There," the Beach Boys' "In My Room," Zeppelin's "Since I've Been Loving You" and on up to the entire album, Nebraska, by Bruce Springsteen.
I am, for the most part, in agreement as to the sorrowful themes expressed in most of the songs I have listed. But for each of those, there was also many recommendations of "Seasons in the Sun," "Alone Again," 'Two Out of Three Ain't Bad," "Starry, Starry Night," "Mandy," and "Song Sung Blue." I was occasionally tempted to smile but realized that the subjective boundaries of sorrow are often marked with the bizarre totems: tiny putti angels, commercials for telephones, and maudlin Hallmark poetry reducing even the most resolute of stoics to tears.
Amidst all of litany from above, two genres of music were often conspicuously absent: Blues and Jazz - two of the most remarkable contributions of American Culture to the world. I have always thought it curiously ironic that the most obvious answer as to what was the saddest music, the Blues, was most often overlooked. Sadness and sorrow are the very core of what defines the Blues.
Admittedly, this is a difficult question. It is informed by difficulties of age and experience, of not being able to find sympathy with the more complicated sorrow at the heart of certain works of music. This immediately presents the contingent difficulty of being able to recognize the meaning of an expression of deep sorrow. It is certainly a sad event to have one's kitten die. I'm sure there is music that has been occasioned by such sorrow. And as hesitant as I am to diagram a scale of sorrows here, the death of a parent, a lover, would certainly sink to a deeper depth of sorrow than that of the kitten. And as difficult as these may be, they are still overwhelmed by the incomprehensible sorrow brought forth by the death and suffering of multitudes of human beings in wars, genocides and disasters. What music, what human expression, can redeem - and here the language stresses and warps under the limits of reference and grammar - but what can be done to express such an overwhelming sorrow of being in the face of such catastrophe?
I do not believe that there is any higher expression of human being than that which radiates out of music. Levi-Strauss stated that "the invention of melody is the supreme mystery in the sciences of man." Fortunately, as Eliot claimed, human being cannot bear very much reality. Our nervous system is wired to de-sensitize us over repeated exposures, to habituate us, as it were, to sorrow. But now and then, listening to music which attempts to redeem the sorrows of existence, we get a glimpse of what we are being "protected" from. Beauty rises like sparks of fire from the blackness of the Abyss.
Do I have an answer to my question? Nothing satisfactory. Obviously, the question precipitates an intensely subjective response. And even within this proscribed arena of subjectivity, experience, the knowing of the music, continually hungers for innocence, to be able to return to the first time the music unfolded within you. Music is weirdly rich with this sort of infinitesimal calculus of longing. A veil is suspended before us, shimmering with melody, tone and rhythm, presenting glimpses of the divine beyond its finely woven warp and weft. In great music, in the saddest music, there is always an intimation of something transcendent, some quality that defeats language, escapes memory. It is always as if we try to see through the veil and are continually distracted back to what is being projected upon it. Always, this longing.
As I stated earlier, I am in accord with the above recommendations. But I have a few (all links go to YouTube):
Beck - Lost Cause
Beethoven - Funeral March, Sym. No 3, Eroica
Blaze Foley - If Only I Could Fly
Chopin - Nocturne in E Minor, Op. 72
Ry Cooder - Paris, Texas
Miles Davis - Blue in Green
Al Green - Tired of Being Alone
Ted Hawkins - The Good and the Bad
Billie Holliday - Strange Fruit
Son House - Death Letter
Iron and Wine - He Lays in the Reins
Etta James - Anything To Say You're Mine
Skip James - Hard Time Killing Floor
Blind Lemon Jefferson - Nobody's Fault But Mine
Blind Willie Johnson - Dark Was the Night, Cold Was the Ground
Robert Johnson - Hellhounds On My Trail
Liszt - Rhapsody No. 5
Duke McVinnie - Ginny
Henry Mancini - Moon River
Stephen Micus - Music of Stones
Van Morrison - Streets of Arklow
Graham Parsons - A Song For You
Oscar Peterson - I Love You, Porgy
Portishead - Glory Box
Damien Rice - The Blower's Daughter
Joaquín Rodrigo - Concierto de Aranjuez
Schubert - Trio in E Flat, Op. 100, 2nd mov
Andres Segovia - Passacaille
Harry Dean Stanton - Cancion Mixteca
Townes Van Zandt - Tecumseh Valley
Anne Sofie von Otter - Oblivion Soave
Tom Waits - Martha
Gillian Welch - Revelator
This list could go on and on. Omissions multiply with each new entry. I could write a book on each piece. Finally, I give the last word to George Steiner - not so much music as a meaningful sound. But I do believe that this is up there with the saddest:
A Whistle: The recording of the whistle in the painting labelled 'By the Master of the Chambèry Passion'. "It is a Crucifixion on gilded panelling which can most plausibly be dated mid-fourteenth century and ascribed to one of the workshops in the Turin area.... It is the red-headed lad in the attendant crowd [of those witnessing the Crucifixion], the fourth figure from the left, who arrests the attention. He is whistling. On two supple fingers inserted, shepherd - or street urchin style, into a corner of his full lips. Whistling either to himself or some listener - a crony, a sheep-dog, a girl - outside the scene. There can be no mistake. The whistle is a loud and joyous one, as of a thrush on a spring upland. The whistler's firm green-hosed legs tell us that, as does the merry swelling of his throat and cheeks. And though his lips are pursed, there can be no doubt as to the smile and the dawn cheer which gives them breath. Yet the young man's eyes are on the Cross, on the twisted flesh and the petals of bright blood around the nails. The eyes are unwavering as he whistles, as the pure clear merriment rises into the paschal air."