100 Saddest Songs of All Time

1.
ADAGIO FOR STRINGS—SAMUEL BARBER
Written by American composer Samuel Barber while on a retreat in Venice, “Adagio for Strings” has become the international sound of sadness. It was first performed by the NBC Orchestra under the direction of conductor Arturo Toscannini in 1938 and was chosen on the fly by shocked radio broadcasters following the unexpected death of President Franklin D. Roosevelt in April 1945. It has since been used in countless funerals (including those for Albert Einstein and Princess Grace of Monaco), was a pivotal aspect of Oliver Stone’s 1986 film, Platoon, and was the first choice of music programmers following the events of September 11, 2001. In 2004 it was named the saddest song ever by a BBC user poll.

2.
STRANGE FRUIT – BILLIE HOLIDAY
Written by Jewish high school teacher Abel Meeropol and definitively performed by Billie Holiday—though the song was not written for the singer as she liked to claim—there is no stronger condemnation of the sadness and horror of bigotry in song than “Strange Fruit.” The unforgiving imagery of “bulging eyes” and “twisted mouth” sets up the palpably unsettling dichotomy between fruit and flesh that plays out in the final verse as the crows descend, the rain falls, and the sun rots a “strange and bitter crop.

3.
IN DARKNESS LET ME DWELL – JOHN DOWLAND
The most modern of John Dowland’s Elizabethan lute songs, one can easily draw the line from “In Darkness Let Me Dwell” to every modern master of gloom. One of Leonard Cohen’s myriad nicknames may be “the Godfather of Gloom,” but that title rightly belongs to Dowland. 

4.
MARIE—TOWNES VAN ZANDT
Townes Van Zandt wrote more than his fair share of gentle heartbreakers, but the simple narrative of “Marie” is spun from so much tragedy that it is often in danger of toppling into farce. The story of a homeless and broke rail worker who meets a woman he loves, attempts to find her food and clothing, gets her pregnant (“In my heart I know it’s a little boy / Hope he don’t end up like me”), and then wakes up one spring morning to find her dead (“my little boy safe inside”) is performed by Van Zandt with such plainspoken despair it makes the world he paints seem nearer and more real than most have ever imagined it could be.

5.
RANK STRANGER – STANLEY BROTHERS
Written by the prolific and now oft-forgotten gospel songwriter Albert E. Brumley—apocryphally credited with composing some 800 songs in his lifetime—“Rank Stranger” was first published in 1942 under the title, “Rank Stranger to Me,” and may arguably be the most lugubriously evocative song to address the old adage, “you can never go home again” ever cut into acetate. First recorded by the Stanley Brothers in 1960 the song relates a simple bluegrass ballad of a man returning to his “home in the mountains” only to find that everyone he knows—including his “mother and dad” and all his friends—have passed away and are waiting for him “by the bright crystal sea.” The song remains one of the Stanley Brothers’ most popular and in 2008 their 1960 recording was added to the National Recording Register.

6.
I’M SO LONESOME I COULD CRY – HANK WILLIAMS
Johnny Cash once told Bob Dylan that it was the saddest song he’d ever heard and artists as diverse as Ray Charles, Dean Martin, Cassandra Wilson, Diamanda Galás, and the Mountain Goats, among many others, have recorded it, but “I’m So Lonesome I Could Cry” wasn’t even originally intended to be a song, per se, rather it was earmarked by Williams to be one of the more obscure recitations of his alter ego, Luke the Drifter. Nervous that the imagery and metaphors of the lyric would be too pretentious for his audience Williams tried the song out on his band, which enthusiastically suggested he record it, which he did. Williams would later note it as his personal favorite, though when it was released in 1949 it appeared as a B-Side to the decidedly more prosaic, “My Bucket’s Got a Hole In It,” perhaps his concerns over its lyric use of language not completely calmed. The original recording is a masterpiece, but it’s the surprisingly slower live recording captured during one of Williams’ Mother’s Best performances—officially released for the first time in 2008—that best serves the song’s lugubrious sentiment. 

7.
ONLY THE LONELY – FRANK SINATRA
The Chairman of the Board devoted much of his mature career to plumbing the depths of loneliness, heartbreak, and regret and its arguable that no song captures Sinatra’s late-night emptiness as “Only the Lonely” does. Written by Sammy Cahn and Jimmy Van Heusen specifically for the singer, and given a consoling arrangement by Nelson Riddle, Sinatra squeezes every bit of pathos from the lyrics, and as he recalls “picnics at the beach when love was new” and philosophizes from his bar-side lectern that the “hopeless little dream” of love may only come but once, there’s no denying he believes every word.

8.
NOTHING COMPARES 2 U: SINEAD O’CONNOR
“Nothing Compares 2 U” was initially written by Prince for the Minneapolis band The Family, and first appeared in 1985 on their lone eponymous album, but when Sinead O’Connor chose to include it on her 1990 album, I Do Not Want What I Haven’t Got, she took full possession of the song, infusing it with an inconsolable heartsickness born of her own emotional turmoil. A video that featured little more than a close-up of O’Connor’s face as she sings—and a pair of unplanned tears shed in the final verse—helped the song reach number one in pretty much every country in the Western Hemisphere, while Pitchfork has since placed it at #37 in their list of the Top 200 Tracks of the ‘90s and Rolling Stone placed it at #165 in their 2010 Greatest Songs of All Time list.

9.
CAROLINE, NO – BEACH BOYS
Is there any more gorgeously rueful monument to lost innocence in pop music than “Caroline, No,” or any line more heartbreakingly breathtaking as Brian Wilson’s confessional, “It’s so sad to watch a sweet thing die”? Originally released as a Brian Wilson solo single in March 1966 (it stalled at #32), before appearing weeks later as the final track on the Beach Boys seminal Pet Sounds album, “Caroline, No” features only Brian Wilson on vocals, who had original titled the song “Carol, I Know,” but after lyricist Tony Asher—whose girlfriend had recently moved to New York and cut her hair, providing inspiration for the song’s opening lines—misheard it as “Caroline No” the pair decided to keep the new title. The song’s coda—Brian’s dogs, Banana and Louie, barking at a passing train—gives the song’s sense of loss additional depth. In a 1989 interview Wilson said that the song reflects the feeling that “once you’ve fucked up, or once you’ve run the gamut with a chick, there’s no way to get it back,” concluding the sentiment by saying, “I just felt sad, so I wrote a sad song.”

10.
DISINTEGRATION LOOPS 1.1 – WILLIAM BASINSKI
A 21st century lament born beneath the furling, black dust clouds that drifted from lower Manhattan on 9/11 and the preceding days, “DLP 1.1” blots itself into being in a cycle of destruction that takes just over an hour. It is the sound of a mechanical heartbeat crawling to a stop, the breath slowly seeping from the speakers; the sound of technology giving into its own obsolescence, removing itself from the equation; and it’s the sound of America’s sorrow in the face of her lost innocence and naiveté. “DLP 1.1” is built from a brief synthesizer loop of ponderous melancholy Basinski composed and captured on tape in the early 1980s. While transferring the tapes to digital sources in September 2001 (while the planes were hitting the towers) the composer found that the old, analog ribbons were eroding and chose to create a new piece based on their deterioration: As the loop plays the tape decays and the solemn, pastoral melody degrades into silence.

11.
TENNESSEE WALTZ – PATTI PAGE
She was the sound of post-war America, the sweet voice of America’s spread to the suburbs (“The Doggie In the Window”), but Patti Page’s 1950 rendition of the Redd Stewart/Pee Wee King country standard, “Tennessee Waltz”—first recorded in 1947 by Cowboy Copas and initially pegged as a B-Side for Page’s novelty song, “Boogie Woogie Santa Claus”—has sold 10 million copies making it both the biggest selling single by a female artist and the best selling country music song of all time. The simplicity of the song is not lost on Page: “Someone introduces their boyfriend to someone else, and now he's no longer her boyfriend. It's just a sad love song,” but the simplicity is what makes it so heartbreaking as she relives the memory in perpetuity, recalling clearly the waltz burned into her memory, reminding herself over and over of “just how much I have lost.” 

12.
LAST NIGHT I DREAMT THAT SOMEBODY LOVED ME – THE SMITHS
Morrissey considered “I Know It’s Over” (which topped a 2004 BBC poll of songs people listen to when they’re sad) to be little more than a sketch for “Last Night I Dreamt That Somebody Loved Me,” and many hardcore Smiths fans, as well as guitarist Johnny Marr himself, consider the song to be the ultimate distillation of the group. No surprise then that “LNIDTSLM” is also among their most bleak, opening with nearly two minutes of a stark piano figure accompanied by the unsettling hysteria of a miners strike before sparking to life as a dazzlingly slow orchestral dirge, where love is found, as Roy Orbison put it, “only in dreams.” It’s a surprisingly laconic song for Morrissey, missing any hint of the black comedy he liked to dust over his lyrics—but it allows him to stretch the notes for all they’re worth, and when he sings “The story is old, I know, but it goes on” he could be winking to the long history of lovelorn pop and his own brief history with the Smiths, as well as stating the obvious. (As if it needed anything else to recommend its melancholic pedigree, “LNIDTSLM” also stands as the final Smiths single, released in December 1987, months after the group had already fallen apart.)

13.
DARK WAS THE NIGHT, COLD WAS THE GROUND – BLIND WILLIE JOHNSON
When Ry Cooder referred to “Dark Was the Night, Cold Was the Ground” as “the most soulful, transcendent piece in all American music” his enthusiasm wasn’t as hyperbolic as it may first appear. Deeply religious from his early youth, Johnson had, perhaps, a more clearly defined understanding of the soul than many of his peers, while adding to the song’s metaphysical aura is the fact that it features no lyrics, only its foreboding title and Johnson’s haunting falsetto cries, which seem to lift his playing from the merely sublime to the unarguably profane. Facts at hand it’s not hard to understand why “Dark Was the Night…” was included on the golden record that accompanied Voyager 1 and 2 into the vast emptiness of space as evidence of the intelligence and diversity of life on Earth.

14.
DIDO’S LAMENT” FROM DIDO AND AENEAS – HENRY PURCELL
Though Purcell composed with little acclaim in his lifetime, and missed the operatic fervor that swept through London just fifteen years following his death in 1695, “Dido’s Lament” remains one of the greatest moments in the history of the genre. The devastating anguish captured in the brief composition punctuates the story of Dido, the queen of Carthage, and Aeaneas, a prince of Troy, who fall in love before all manner of supernatural twists lead to their separation, whereupon Dido sings this famous lament and commits suicide. The aria features exemplary chromatic texture and offers an early and impressive use of ground bass, or basso ostinato, a form in which a structurally pronounced bass pattern is repeated with shifting variations in the melodies above. “Dido’s Lament” has been interpreted by contemporary performers such as Klaus Nomi (under the title “Death”), Alison Moyet, and Jeff Buckley, a testament to the lugubrious power of the lament over 300 years since its composition.

15.
HOLOCAUST – BIG STAR
When Alex Chilton and Jody Stephens entered the studio to record Big Star’s third album in 1975 the band, as such, had ceased to exist, but what was caught on tape—the dark and inelegant implosion of Chilton’s dreams of rock ‘n’ roll glory—stands as one of the greatest achievements in rock history. It even topped a 2000 NME ranking of the most heartbreaking albums of all time and “Holocaust” is the black hole at its frayed and disturbed center. Harrowing is almost too light a descriptor for this end-of-the-rope, edge-of-the-world piano dirge that finds Chilton—dejected, bitter, exhausted, and alone, propped up by a ghostly pedal steel and a muddy upright bass—exploring the fine line between unconscious life and conscious death: “You’re a wasted face. / You’re a sad-eyed liar. / You’re a holocaust.”

16.
AULD LANG SYNE – GUY LOMBARDO
A Scottish poem and folk melody that both took a long, circuitous route before being appropriated and combined by poet Robert Burns in the late 18th century, “Auld Lang Syne” became a widespread U.S. tradition not long after Canadian bandleader Guy Lombardo arranged the song for his band, The Royal Canadians and performed it during a 1929 New year’s Eve radio broadcast. Lombardo’s popularity with the song was such that he wrote in his 1975 autobiography, Auld Acquaintance, that at times his band was “booked on NBC to play until a minute to midnight and on CBS on the stroke of the new year.” Despite its ubiquity, few can utter more than the first line—“Should auld acquaintance be forgot and never brought to mind?”—and fewer still know what “auld lang syne” stands for: roughly, “times gone by” or “times long past.”

17.
WHO KNOWS WHERE THE TIME GOES – NINA SIMONE
Originally written and performed by English folk-singer Sandy Denny (first with the Strawbs in 1967 and then with Fairport Convention in 1969), but it’s the version Nina Simone recorded for her 1970 live album, Black Gold, complete with a classic Simone pre-song speech—“Time is a dictator as we know it. Where does it go? What does it do? Most of all, is it alive?”—that reveals the song’s mysterious sadness. Not only do Simone’s dusky  vocals bring more depth to the searching lyrics, but her short piano solo midway through the song is a gorgeous interlude that fuses her classical training to her interest in modern folk. 

18.
PAST, PRESENT AND FUTURE – THE SHANGRI-LA’S
Recited over the main melodic line from Beethoven’s “Moonlight Sonata,” “Past, Present and Future” is a bleak slice of conceptual spoken word art from a girl group who thrived on heartache (“Leader of the Pack,” I Can Never Go Home Anymore”) that suggests both the disillusionment of heartbreak, but also implies the memory of rape as singer Mary Weiss emphatically asserts “don’t try to touch me, ‘cause that will never… happen… again” before suggesting, “Shall we dance?” at the bridge, the song flowering for the briefest moment of baroque joy before dissolving into “The future” brings about Weiss’ weepy conjecture that “maybe someday I’ll hold someone’s hand” before concluding “I don’t think it will ever happen again.”

19.
THE LAST LETTER - REX GRIFFIN
The flip to jukebox hit, “Over the River,” Rex Griffin wrote and recorded this tuneful suicide note in 1937 after the breakup of his first marriage. One of the earliest examples of disarmingly intimate and confessional country music, the song’s softhearted pace warmly carries the wearied resignation of the lyric: “To this world I will soon say my farewell, at last / I will be gone when you read this last letter from me.” It was a hit again for Jimmie Davis in 1939 and that year Griffin released “Answer to the Last Letter” to address the post-mortem regrets of those left behind. “The Last Letter” has since been covered by Ernest Tubb, the Carter Family, Gene Autry, George Jones, Willie Nelson, Waylon Jennings, and The Daytonas, and Dylan even borrowed the melody for his “To Ramona.”

20.
GLOOMY SUNDAY – BJORK
Written in 1933 by Hungarian composer Rezső Seress, with lyrics by poet László Jávor, “Gloomy Sunday” was first marketed in America as “The Famous Hungarian Suicide Song.” Though dozens have performed this bleak ballad it has more-or-less belonged to Billie Holiday since she had a hit with it in 1941, but in recent years idiosyncratic Icelandic singer Björk has successfully claimed the song as her own, first recording it with big band accompaniment in 1998 for a Walden Woods Project fundraiser, and more recently performing an unworldly rendition at the 2010 funeral services for fashion designer Alexander McQueen.

21.
SOMETIMES I FEEL LIKE A MOTHERLESS CHILD – PAUL ROBESON
Certainly one of the most well-known recordings of this traditional song with roots in slave spirituals of the 19th century, there’s a fascinating dichotomy at play between Robeson’s measured, astonishingly strong baritone, and the fragility of the “motherless child” lyric. Some later performers toy with those lyrics, ditching the haunting, “Sometimes I feel like I’m almost gone,” second verse for attempts at reaching a more modern audience—Jimmy Scott’s fantastic version replaces it with “This world out here is lonely and cold,” while Van Morrison opts for the considerably more dippy “Sometimes I wish I could fly like a bird up in the sky.”—but the dire metaphysical imagery locked in the performer disappearing before our very eyes is strikingly poetic and predates Thom Yorke’s paranoid ballads by more than a century.

22.
I WISH MY BABY WAS BORN – DILLARD CHANDLER
A traditional ballad performed without accompaniment by keeper-of-the-Appalachian-holler, Dillard Chandler. Born in 1907, Chandler was a shy and illiterate logger who lived in the thick woods of North Carolina and learned a deep repertoire of songs in his youth, which were captured during the mid- to late- 1960s by John Cohen—who also made the stunning 1973 short film, The End of an Old Song, about the singer’s life and struggle to define himself in a modern world. Chandler’s take on “I Wish My Baby Was Born” is brief, running just over a minute in length, but it takes just 15 seconds for your heart to break as he sings the opening line, “I wish, I wish my baby was born / And sitting on its papa’s knee.” The song has been recorded by Uncle Tupelo (1992), The Be Good Tanyas (2003), and came to popular attention after Tim Erikson, Riley Baugus and Tim O'Brien performed it on the Cold Mountain soundtrack (2003), but as wonderful as these renditions may be, it’s difficult to supplant Chandler’s richly aggrieved voice.

23.
NOT DARK YET – BOB DYLAN
Teaming once again with producer Daniel Lanois—who produced 1989’s exceptional Oh Mercy—Dylan explored the realities of a third act with dispirited resignation in “Not Dark Yet,” the first single from 1991’s Time Out of Mind. With the light narrowing, Dylan is scarred, jaded, tired and insensate, ending each of the four verses that comprise the song with a grim reminder that “It’s not dark yet, but it’s getting there.” Lanois—who preferred an unreleased demo version of the song to the final “civil war ballad” that appeared on TOOM—envelopes the song in atmospheric organ and layers of coruscating guitar, matching Dylan’s “vacant and numb” lyrics. Likely to stand as his late-career summit, “Not Dark Yet” is as bleak as Mr. Zimmerman has ever been. 

24.
ALABAMA – JOHN COLTRANE
Opening with a sorrowful melody—that some have suggested, without attribution, is based on a Martin Luther King, Jr. speech—drifting over a tremulous, rumbling piano, John Coltrane’s “Alabama” takes all the pain of the September 15, 1963 bombing of the 16th Street Baptist Church in Birmingham, Alabama that killed four young black girls, and pours it into just over five minutes of weary heartache and inventive catharsis. “Alabama” is one for the ages in both message and meaning. It can be found on the 1963 album, Live at Birdland, though it was actually recorded in the studio over a month after the Birdland concert.

25.
YOU FORGOT TO ANSWER – NICO
Over the course of two albums that helped lay the foundation of goth, former Velvet Underground chanteuse Nico—with a fair amount of help from another VU ex-patriot, John Cale—crafted a challenging sound that married Nico’s stern Nordic vocals to the haunted, distancing drone of her weapon of choice, the harmonium. “You Forgot to Answer,” the third track on her stunningly desolate 1974 album, The End, relates her heartbreak after attempting to reach her former lover, The Doors’ Jim Morrisson, on the telephone, only to find out later that as she was calling he was seated, dead, in his Paris hotel bathtub. Her misery at this missed connection pours out over waves of howling, atonal anguish as she sings, “The high tide is taking everything and you forget to answer.”

26.
DER ABSCHIED (DAS LIED VON DER ERDE) – GUSTAV MAHLER
Arranged for two solo voices and orchestra, Mahler’s Das Lied von der Erde (The Song of the Earth) was inspired by the publication of Die Chinesische Flöte (The Chinese Flute), German translations of ancient Chinese poetry. Conceived and written on the heels of three painful events in the composer’s life, including the death of his daughter, Maria, Mahler considered Das Lied his most personal artistic statement. “Der Abschied” (“The Farewell”), the final of six movements, runs almost as long as the other five combined and draws on the intensity of the composer’s loneliness and existential misery—“My heart is still and awaits its hour.” Das Lied premiered after Mahler’s death in 1911 and was conducted by his close friend Bruno Walter who recalled first pouring over the score that the frail composer had handed him, noting its funereal relevance as the “last confession of one upon whom rested the finger of death.”

27.
TAPS – TRADITIONAL
Written in July 1826 by Union General Daniel Butterfield as revision to the infantry call to Extinguish Lights into a somber and moving 24-note bugle call. “Taps” is quickly picked up by other troupes and later, on a tense evening with Confederate soldiers mere feet from his position, a battery captain overseeing a soldier’s burial decided to sound “Taps” as an alternative to the traditional three-gun salute, which he worried would ignite a flurry of return fire. The mournful music quickly became a military standard and is recorded as being played by both Union and Confederate armies within months and became an official part of military field manuals for “lights out” as early as 1863, and in a funereal capacity as early as 1891.

28.
CRYING – ROY ORBISON
The Big O specialized in operatic pop sorrow and “Crying,” from 1961, which he claimed to be autobiographical, is one of the greatest and most grief-stricken moments in all pop history. Written by Orbison with Joe Melson, the entire song is an anguished inner monologue swirling around a brief moment, frozen in shellac, as the singer unexpectedly bumps into a former lover who holds his hand as she says “hello.” The moment is excruciating and even simple lines like “you wished me well” hit with phenomenal force and as the brief song closes Orbison’s trembling voice lifts off: “Now you’re gone / and from this moment on / I’ll be crying.” 

29.
HURT – JOHNNY CASH
Cash hesitated to record “Hurt” when it was first brought to him by producer Rick Rubin. The song, written by electro-goth kingpin Trent Reznor and originally appearing as the final cut on Nine Inch Nails’ 1994 album, The Downward Spiral, was dark stuff. Even Cash’s son, John Carter Cash, was concerned that the “hopelessness of it seemed almost like a little too much.” In the end Rubin won out and “Hurt” was on the lineup when American IV: What Comes Around was released in November 2002. The song became Cash’s final single and was accompanied by a controversial video that featured a broken, wet-eyed, shaking Cash that some viewed as exploitative of the singer’s declining health, but the power of the song and richness of Cash’s performance overwhelms any such concerns; its ruminative qualities taking on new meaning as the 70 year-old country rebel asks “what have I become?” and painfully confesses, “I will let you down, I will make you hurt.” Cash so occupied the song that when Reznor finally took in this new version of his deeply personal song he “welled up with tears,” saying “I knew it wasn’t my song anymore.”

30.
HALLELUJAH – JEFF BUCKLEY
Buckley’s version of Leonard Cohen’s “Hallelujah” has become the de facto interpretation. Though John Cale gets the credit for plucking it from Cohen’s songbook and breathing into it a place in pop culture, Buckley’s version became a posthumous number one in 2008 for the singer-songwriter—who died mysteriously while swimming in Tennessee’s Wolf River in 1997—and was named one of the 500 Greatest Songs of All Time by Rolling Stone. (For more about “Hallelujah” see page 000)

31.
ST. JAMES INFIRMARY BLUES – LOUIS ARMSTRONG (1959 VERSION)
Based on an old anonymous English folk song called, among many other things, “The Unfortunate Rake,” and freely tweaked until songwriter Irving Mills (under the pseudonym Jow Primrose) won the rights to the title and his 1930 arrangement of the song, “St. James Infirmary Blues” has been recorded, under various titles (“St. Joe’s Infirmary,” “The Gambler’s Blues,” etc.), by too many artists to name—Cab Calloway, Django Reinhardt, Billie Holiday, Andy Griffith, the Stray Cats, and the White Stripes among them—but it was Louis Armstrong’s 1928 recording with his Hot Five (renamed the “Savoy Ballroom Five” for the session) that first brought the song to a wide audience. No matter what version you listen to, the first verse is usually about a young man who goes to visit his “baby” who is “stretched out on a long white table,” dying in Saint James Infirmary. After the first verse though, it’s a free-for-all. Most existing versions are lyrically clunky and filled with mixed messages, which may or may not concern themselves with any combination of alcoholism, prostitution, gambling, and/or venereal disease. Even Armstrong recorded multiple versions throughout his career, but the version Pops recorded with his All-Stars for Decca in 1959 gives the song an unremittingly somber, stately pace—it crawls compared to his highly regarded 1929 version—that suits the material remarkably well.

32.
HE STOPPED LOVING HER TODAY – GEORGE JONES
Often named the greatest country song of all time, “He Stopped Loving Her Today,” was written by Bobby Braddock and Curly Putman and proved to be one of George Jones’s biggest hits when it was released in 1980. The song’s narrative uncovers how deep the well of pain at the heart of unrequited love can go (“He kept her picture on the wall / Went half crazy now and then”) and the late chorus that follows four consecutive verses provides a dark, O. Henry twist as Jones reveals the chorus (“He stopped loving her today / They placed a wreath upon his door”). It’s as solemn a twist on ‘til death do we part that exists anywhere in song.

33.
SONG TO THE SIREN – THIS MORTAL COIL
Written by Tim Buckley and Larry Beckett and chosen by 4AD co-founder Ivo Watts-Russell as the first single for his This Mortal Coil covers project, “Song of the Siren,” performed by foils Elizabeth Fraser and Robin Guthrie of the Cocteau Twins, is a breathtakingly gorgeous slice of dark, shimmering ambient pop that, in Watts-Russell’s own words, “You'd have to be either deaf or dead not to be moved by.” 

34.
MILLE REGRETZ – JOSQUIN DES PREZ
Josquin des Prez—like Madonna he is often referred to as just, Josquin—was massively popular in his day (16th century) and was among the first composers to truly infuse his works with a holistic expression of emotion: “Mille Regretz” (One Thousand Regrets) being a prime example. Written and gifted to Charles V, in 1520, this sorrowful polyphonic chanson is said to have been the Emperor’s favorite song, hence it’s colloquial handle, “The Emperor’s Song,” and it remains popular due to the simplicity and power of its touching melody and anguished text: “A thousand regrets to leave you / And to be far from your loving face. I suffer such deep sorrow and grievous anguish / That soon I will end my days.”

35.
DARK END OF THE STREET – JAMES CARR
Perhaps the best cheating song of all time, this maudlin soul ballad cuts to the guilty heart of running around without any pretense as the two lovers live “in darkness to hide alone,” know they’re doomed to “pay for the love” they stole, but can’t help from meeting in the shadows. Written by Muscle Shoals songwriters Dan Penn and Chips Moman during a break from a card game, it’s hard to believe that upon its release in 1967 it peaked at only 77 on the pop charts. Carr’s deep and sensitive performance is among his best and his rendition remains definitive despite numerous challengers including Percy Sledge, Aretha Franklin, Bruce Springsteen, and Cat Power to name just a few.

36.
NE ME QUITTE PAS – JACQUES BREL
Translated as “Don’t Leave Me,” tall, dark, and handsome Belgian chansonnier Jacques Brel swiped a bit of melody from Franz Liszt’s Hungarian Rhapsody and painted over it with characteristically bleak pleas like “I’ll give you pearls of rain from countries where it never rains.” After all the poetic needling Brel ends the song by resorting to a more simplistic plea, repeating over and again, “Don’t leave me, don’t leave me, don’t leave me…”

37.
SHIPBUILDING – ROBERT WYATT
When producer and composer Clive Langer heard Robert Wyatt’s version of “Strange Fruit” he was so moved that he set to work fashioning a song for the idiosyncratic singer, but as he struggled to find a lyrical foothold a fortunate meeting with Elvis Costello led to the young Mr. McManus penning a poignant humanist response (“the best words I’ve ever written,” he declared) to the short-lived 1982 Falkland Islands conflict between Argentina and the United Kingdom and the chilly, indifference of war. Wyatt—a galvanic political creature—endowed the words with staggering pathos as he sang of remorseful fathers preparing to build the ships that will take their sons to their deaths (“Within weeks they’ll be re-opening the shipyard and notifying the next of kin”) imagining that they will be “diving for dear life” when they should be “diving for pearls.”

38.
HIGHWAY PATROLMAN – BRUCE SPRINGSTEEN
Included on his stark 1982 masterpiece, Nebraska, “Highway Patrolman” is among the greatest narrative songs ever written and is a testament to the unbreakable bonds and unavoidable torments that attend family. The plainspoken narrator, Joe Roberts, is a sergeant with the highway patrol and when he ends the first verse by introducing his brother Franky by saying only that he “ain’t no good,” there’s little doubt that a bad moon waits over the horizon. During the chorus Joe’s memory returns to earlier, better times, but during the verses their lives diverge as Franky ships off to Vietnam and Joe marries and unsuccessfully attempts wheat farming. Joe winds up a highway patrolman and Franky returns from the war and the slow fuse is already lit. In the final verse, Franky attacks a man in a bar and steals a car. Joe chases after him, but as he speeds by a sign saying they’re only five miles from the Canadian border, he realizes he needs to let him go. Joe corrupts his integrity and says goodbye to his brother as he watches the taillights disappear. The power of narrative was not lost on Hollywood as Sean Penn loosely adapted the song into the screenplay for his 1991 directorial debut, The Indian Runner.

39.
MY MOM – CHOCOLATE GENIUS
Not many musicians have tackled the slow devastation of Alzheimer’s, but Marc Anthony Thompson—A.K.A. Chocolate Genius—does so with shattering results in “My Mom” from his 1998 album, Black Music. A whorl of bleak organ, muffled drums and delicate acoustic guitar circle Thompson’s husky vocal as he narrates a visit to his parent’s home. The tender details—“that tree was a goalpost,” “that mirror it was a crowd,” it even “smells just the same”—accumulate as the verses spiral downward, finally resting at a spare chorus, Thompson touchingly singing, “My mom, my sweet mom / She don’t remember my name.” Simply heartbreaking.

40.
LUSH LIFE - JOHN COLTRANE AND JOHNNY HARTMAN
The complex emotional and intellectual bite of Billy Strayhorn’s greatest composition is even more shocking for the fact that he began writing it when he was just sixteen. It took him five years to slowly piece the song together and he never imagining he would actually publish it, but it has since gone on to become something of the Great American Songbook’s dark night of the soul. Strayhorn’s faraway glance witnessing a life outwardly successful (jazz, cocktails, trips to Paris) but filled with emptiness. The stoic protagonist desperately pointing out the silver linings of a life touched by unfulfilled desires, a theme that may point to Strayhorn’s youthful struggles with his homosexuality. Originally titled “Life is Lonely” and, in an arrangement for the Duke Ellington band that the group never performed, “Lonely Again,” but it was Nat King Cole’s 1949 version as “Lush Life” that placed the song in the popular consciousness. However it didn’t find its true owners until John Coltrane and Johnny Hartman serendipitously added it to the studio sessions for their eponymous1963 album, perfectly crystallizing the song’s gentle, near-magical sadness.

41.
THE SAME DEEP WATER AS YOU – THE CURE
Robert Smith and Co. were never so drenched in miasmatic despair as they were on 1989’s Disintegration, the bleakest beacon of which was the nearly ten minutes of floating darkness, “The Same Deep Water As You.” All of the group’s musical trademarks—long synth lines, echoing drums, forlorn leads—are represented, all loping over the ambient sound of a distant thunderstorm. This is radio dirge. Smith’s fragmented lyrics leave a lot to the imagination, but the song seems to suggest the lengths one can go to when truly committed to a relationship, with lines like “kiss me goodbye” and “the strangest twist upon your lips” implying Death with a capital D. While recording the song even Smith was so overcome with emotion that he needed 15 minutes to recover from the its powerful undertow.

42.
HOPE THERE’S SOMEONE – ANTONY AND THE JOHNSONS
Antony and the Johnsons became indie-rock darlings with the release of their second album, 2005’s I Am a Bird Now, and the opening track, “Hope There’s Someone”—a solemn plea for comfort and understanding—was eventually names the best single of 2005 by Pitchfork. Transgender singer Antony Hegarty’s haunting vocal imbues an otherworldly anguish to a song that recalls everything from madrigal laments and turn-of-the-century spirituals to the circuitous minimalism of Philip Glass and the most smoldering torch songs you can name.

43.
REMEMBER MY FORGOTTEN MAN – JOAN BLONDELL, ETTA MOTEN
An infamous musical sequence from the Busby Berkeley film, Gold Diggers of 1933, “Remember My Forgotten Man” was written by Harry Warren and lyricist Al Dubin as a reaction to F.D.R.’s famous “Forgotten Man” speech of April 7, 1932, and the pair even constructed the song’s three verses to echo the speech’s themes (WWI, the farmer, and finally the family). Joan Blondell performs the song in the film, but is actually lip-syncing over vocals laid down by singer Etta Moten. The song summed up the feelings of many Americans following the Great Depression and is still considered one of the greatest musical numbers—despite its dark nature—in the history of film.

44.
HOW TO DISAPPEAR COMPLETELY – RADIOHEAD: Inspired by the works of Scott Walker, Krzysztof Penderecki and Oliver Messiaen, as well as a turn of advice from R.E.M.’s Michael Stipe Re: the slings and arrows of fame, “How to Disappear Completely” is an existential celebrity lament for self-preservation in an exhaustive world of spotlight and surveillance. Originally titled “How to Disappear Completely and Never Be Found,” and released on Radiohead’s consumptive Kid A from 2000, it’s easily the most brittle and crushing ode to the “rigors of touring” trope anyone has ever produced, and that includes Journey’s heartbreaker, “Faithfully.”

45.
HOW CAN YOU MEND A BROKEN HEART – AL GREEN
Written by the Bee Gees’ Robin and Barry Gibb and released as a single in 1971 becoming the group’s first U.S. number one, but when Al Green got hold of the song for his 1972 album, Let’s Stay Together, he took full possession, unearthing the pure, beseeching sorrow at its roots. Though the song exits with a glimmer of hope deep within a broken man (“I got a feeling that I want to live”), the question asked in the song’s title is never addressed. So, how can you mend a broken heart? Maybe there isn’t an answer. 

46.
DIES IRAE – THOMAS OF CELANO
A 13th century Catholic Latin chant ascribed to Italian friar Thomas of Celano, the solemn “Dies Irae” (Day of Judgment or Day of Wrath), is notable for its long run as part of the Roman Catholic Requiem Mass, but in the late 1960s the “Dies Irae,” along with other liturgical songs, were removed from regular mass due their over-emphasis of “judgment, fear, and despair,” but its import remains greater than its current ceremonial standing as it has been echoed and quoted time again for works including Berlioz’s Symphonie fantastique; Haydn’s “Drumroll” Symphony (No. 103); Mahler’s Symphony No. 2; and Mozart’s Requiem Mass. It even pops up prominently in It’s a Wonderful Life, the Nightmare Before Christmas and Star Wars.

47.
DRESS REHEARSAL RAG – LEONARD COHEN
While discussing the mythology behind “Gloomy Sunday” during a 1968 BBC performance—pointing out that a number of people had supposedly committed suicide under the spell of the music leading to an eventual ban of the song—Leonard Cohen closed his remarks by saying: “I have one of those songs that I have banned for myself. I sing it only on extremely joyous occasions when I know that the landscape can support the despair that I am about to project into it. It’s called the “Dress Rehearsal Rag.’ ” The song is one of Cohen’s earliest and its first official recording came on Judy Collins’ 1966 album, In My Life, and Cohen—who believes Collins’ version to be superior to his own—didn’t get around to recording it until the 1968 sessions for his second album. It didn’t make the cut for that album, but he did re-record it for his third album, 1971’s Songs of Love and Hate. “Dress Rehearsal Rag” is a 4 P.M. dirge with bruising accusations that tumble out as he stands at a mirror and attempts a shave, but gets lost in self-hatred, cruel memories about “a girl with chestnut hair,” and blurry, half-mad hallucinations like his transformation from an afternoon depressive to Santa Claus with “a razor in his mitt.” 

48.
THE BLIZZARD - JIM REEVES
Novelist R.S. Surtees once wrote, “There is no secret closer than what passes between a man and his horse,” and “The Blizzard” spins the uniqueness of that relationship into a weary tragedy. One of a string of crossover hits “Gentleman” Jim Reeves racked up in the decade between 1957 and 1967—he continued to chart years after his death in a plane crash on July 31, 1964—”The Blizzard” was written by Harlan Howard, one of the most important country songwriters in history, with thousands of compositions to his credit, including classics like “I Fall to Pieces” and “Heartache by the Number.” It’s the bitter tale of a man and his lame pony, austerely named Dan, struggling through an unforgiving snowstorm. Reeves plies his horse with notions of warm hay, but Dan just doesn’t have the legs beneath him to carry on. “Get up you ornery cuss or you’ll be the death of us,” warns Reeves, but he quickly give sin and the two stop for a rest just “one hundred yards” from home, which is where they’re found at dawn the next day. The song performed well on the charts when it was released as a single in 1963, reaching number four on the country charts and breaking into the pop 100. It’s since been recorded by Tex Ritter, Johnny Cash, Jim Croce, and twee Scottish act Camera Obscura, though none capture the straight-back pathos of Reeves’s original.

49.
YOUR NEW FRIEND – SMOG
Bill Callahan’s brief 1996 EP, Kicking a Couple Around, begins with this minimal and claustrophobic nod to modern love (and his own “Goldfish Bowl” from the previous year’s Wild Love album) as the singer splits with his live-in girlfriend, is banished to his “living-room bedroom” in an achingly small apartment, as loss of privacy echoes his inability to hide his emotionally fragile state. He rebels by blasting his stereo, but the truth is that he would happily die in his chair. Is it delusion or just the complexity of relationships when he reminds her in the final verse, “Don’t get me wrong / I know I’m still your boyfriend”? 

50.
COCKTAILS – DENNIS WILSON
By the time Beach Boys drummer Dennis Wilson went solo with 1977’s Pacific Ocean Blue he had grown dramatically from the group’s weak link into its secret weapon—writing and performing songs with a diarist’s sincerity and husky vocals. Though he had begun work on a second album, provisionally titled Bambu, heavy drug abuse, as well as the sale of the Beach Boys studio, kept him from completing it. One track he did get down is the heartbreaking ballad, “cocktails.” As a glowing synth washes over a delicate piano Wilson, exhausted, explains his truth: “If I was a waterfall I’d fall and flow into you,” but he knows with all his heart that whatever he is, he’s not a waterfall, and the song’s refrain “Por que no dice' que me quieres? (TK)” (Why don’t you say you love me?)—punched up with a proto-Eitzel yawlp—only serves to underline his desperation and confusion.

51.
I SEE A DARKNESS – BONNIE “PRINCE” BILLIE
Will Oldham, recording for the first time as Bonnie “Prince” Billy—he was previously Palace Brothers, Palace Songs, and Palace—released I See a Darkness in 1999. Mojo named it the 20th greatest album of our lifetime and the song that shares the album’s title is the heart-broken centerpiece. The song is both a plaintive recognition of depression’s often-unstoppable hold (“did you ever, ever notice the kind of thoughts I got”) and a hopeful plea for understanding (“A hope that somehow you, you can save me from the darkness”). The song became a touchstone of Johnny Cash’s late-career revival when it appeared on his American III: Solitary Man album, Oldham backing-up Cash’s weathered lead vocal.

52.
I’VE BEEN LOVING YOU TOO LONG – OTIS REDDING
A pleading, slow-burning, gut-wrenching soul standard written by Otis Redding with Chicago soul singer Jerry Butler, “I’ve Been Loving You Too Long” may have peaked at #21 on the pop charts and #2 on the R&B charts when it was released as a single in 1965, but it has since gone on to greater glories, narrowly missing the top 100 in Rolling Stone’s 2010 list of the Greatest Songs of All Time (it came in at #110). Redding’s gritty anguish as he declares, “with you my life has been so wonderful” before falling to his knees and boiling over with more linear overtures (“please, don’t make me stop now”).

53.
DRY YOUR EYES – THE STREETS
Originally written for Coldplay before they realized it would make a better Streets song, Mike Skinner (A.K.A. the Streets) included this surprisingly effective heartbreaker on his loopy 2004 concept album—and most striking picture of modern “English youth”—A Grand Don’t Come for Free, about how a missing bundle of cash (£1000) forces him to re-examine his life. Beneath gently strumming acoustic guitar, distant strings, and a crawling beat Skinner sketches out the graceless details of getting dumped, his stream-of-consciousness lyrics detailing every awkward eye movement and every desperate measure, while the combination of his knockabout Cockney accent (“I’ve got nuffin’, absolutely nuffin’ ”) and the bittersweet vocals of singer Matt Sladen during the chorus, keeps everything grounded. 

54.
L’HYMNE À L'AMOUR (HYMN TO LOVE) – EDITH PIAF
On October 27, 1949 French boxer Marcel Cerdan—long with 47 others, including acclaimed violinist Ginette Neveu—died when his Air France flight from Paris to New York crashed into an Azores mountainside. He was traveling to the U.S. to see his lover, Edith Piaf, who collapsed when she heard the news. Just weeks earlier she had premiered “Hymne à L'amour”—“Hymn to Love” and later, “If You Love Me, (Really Love Me)”—a song she had written (with Marguerite Monnot) as a testament to their love. Following Cerdan’s death the song took on a mythical air of modern tragedy as Piaf sings—presaging the melodramatic misery of groups like the Shangri-Las and the Smiths—“If one day life tears you away from me / If You die far away from me / It doesn’t matter, if you love me / Because I will die as well.”

55.
LORENA – REV. HENRY D. L. WEBSTER / JOSEPH PHILBRICK WEBSTER
This incredibly popular antebellum ballad of the North was actually written in 1857, years before the Civil War broke out, and ironically became a favorite among homesick Southern soldiers who took to naming their settlements, ships and children after the mythical “Lorena.” The songs origins are foggy, but the most popular lineage presents that the music was written by Joseph Philbrick Webster and the lyrics were penned by Rev. Henry D. L. Webster— of no relation— in 1857 and based on the forced dissolution of his engagement to Ella Blocksom in 1849. In her final letter to the young preacher she wrote, “If we try, we may forget,” which eventually found its way into the pining song. Rev. Webster initially changed Ella to “Bertha,” but the song’s melody required an extra syllable and “Lorena”—with inspiration from the lost “Lenore” in Edgar Allen Poe’s, “The Raven”—was written into history. “Lorena” has been recorded by Willie Nelson, Johnny Cash, Slim Whitman, Norman Blake, Bobby Bare, and John Hartford (best known for writing “Gentle On My Mind”), but Waylon Jennings had the most success with his TK version. Worth seeking out though include the brief instrumental version recorded for Ken Burns’ 2005 documentary series, The Civil War; the Mormon Tabernacle Choir’s ethereal recording on the 1992 release, Songs of the Civil War; and Tennessee Ernie Ford’s reverent take from his 1961 album, Civil War Songs of the North.

56.
THE END OF THE WORLD – SKEETER DAVIS
The Shangri-Las may own hold the corner on rough-and-tumble, streetwise brand girl-group grief, but for sickly sweet alienation and the depths of young love’s heartache there’s none more delicately miserable than Skeeter Davis’ December 1962 hit. The world impossibly, cruelly goes about its business—tides still flow, birds still sing—when it should, by rights, be turning to ash and blowing away. It struck a chord and Davis found herself simultaneously gracing the top ten of Billboard’s Pop, Adult Contemporary, Country, and R&B charts, no small feat in 1963.

57.
SADNESS - ORNETTE COLEMAN
A wobbly free-jazz dirge, “Sadness”— recorded live and appearing on the album, Town Hall 1962 –features Ornette Coleman’s weeping saxophone—he constantly struggled to give a “human quality” to his performances—gravely swinging over a bed of uneasy, alien bowed bass, shimmering cymbals and brushed drums. Unreal blue.

58.
OUR SONG – JOE HENRY
About as tearful a dirge about the post-9/11 state of the union (“this frightful and this angry land”) as anyone is likely to write, “Our Song,” from Henry’s 2007 album, Civilians, finds the singer heaping all our hope and love on proud baseball legend, Willie Mays, caught in the act of buying garage door springs at a Home Depot. The song’s narrator ponders the safety of Scottsdale’s distance from tall buildings and our continued desire to celebrate the Greatest Generation, keeping close the thought that “the worst of it might still make [him] a better man.”

59.
FEEL LIKE GOING HOME – CHARLIE RICH
The Silver Fox brought together his love of gospel and his love of country when he wrote what is arguably one his greatest songs. An aching piano ballad that finds the singer chastising himself for a life of mistakes. He finds himself at the end of a long road with the clouds gathering and “without a friend around.” As the song reaches its climax a choir lifts him, “tired and weary,” up towards rolling clouds. It’s an honest and beautiful song from one of country’s most talented—if often overlooked—artists.

60.
TE RECUERDO AMANDA (I REMEMBER YOU AMANDA) - VÍCTOR JARA
A deeply touching song by Chilean activist and singer Victor Jara, “Te Recuerdo Amanda”—first recorded for his 1969 album, Pongo en tus manos abiertas (Into Your Open Hands)—is a portrait of Jara’s mother and father, Amanda and Manuel, and the power of their young love as Amanda runs, smiling, through the wet Chilean streets towards the factory where Manuel, works. During his five-minute break they get to see each other, “all of your life in five minutes,” Jara sings, but when Manuel goes to war he is killed: “in five minutes it was all wiped out.” It’s likely that Jara was simply remembering Amanda’s innocence—tying it to the innocence of his daughter, whom he had just learned was diabetic—but as Pinochet came to power during a military coup on September 11, 1973, the song’s significance changed for listeners around the globe. The morning following the coup hundreds of citizens deemed enemies of the state were rounded up, taken to the National Stadium and, over the following days, beaten and murdered: Jara among them. After an infamous string of political disappearances—estimates range from 9,000 to 30,000 students, journalists, sympathizers and others were disappeared over the following years—the fate of the song’s “Amanda” became more ambiguous, as she stood in for Los Desaparecidos (The Disappeared). “Te Recuerdo Amanda” has since become associated with both Jara and the plight of the Disappeared and was recorded by Joan Baez on her 1974 album, Gracias a la Vida, and by Robert Wyatt on his 1984 Work in Progress EP.

61.
DER LEIERMANN (THE HURDY-GURDY MAN); WINTEREISSE – FRANZ SCHUBERT
Slowly dying from syphilis and hopelessly depressed (“…each morning but recalls yesterday’s grief.”) the shabby and gifted Franz Schubert completed his final masterpiece, Wintereisse (Winter Journey) in the final weeks of his life. A 24-song cycle for voice and piano based on the poems of Wilhelm Müller about a young man who leaves an adopted home after the woman he has given his heart to falls in love with another man. His tears freeze as he wanders and considers slight details of nature’s melancholy beauty, and in the finale, “Der Leiermann” (“The Hurdy-Gurdy Man”), he listens to the music from a scorned and forgotten organ grinder—the piano echoing the cyclical melody of his cheap instrument—as the tired traveler decides this will be his future, mournfully asking, “Will you play music for my songs?”

62.
I (WHO HAVE NOTHING) – BEN E. KING
Best known for his monster hit “Stand By Me,” Ben E. King’s take on “I (Who Have Nothing)” is a brief, bleak, and melodramatic tune based on the Italian song “Uno dei tanti” with lyrics translated into English by Jerry Leiber and Mike Stoller—the duo responsible for many of Elvis Presley’s biggest hits. King plays a forlorn and distanced lover who watches as the woman he loves is showered in diamonds, clothes, and expensive dinners. There is sheepish naiveté as he explains how true his love is, but never is there a sense that it will lead to anything other than misery as he continues to watch her with his “nose pressed up against the window pane.”

63.
BROTHER CAN YOU SPARE A DIME – BING CROSBY
Written by composer Jay Gorney and lyricist E. Y. Harburg (The Wizard of Oz, “Lydia, The Tattooed Lady,” etc.) for their Broadway musical revue, Americana, “Brother Can You Spare a Dime,” became an immediate hit when it premiered—sung by vaudeville ventriloquist Rex Weber—in October 1932, but it was Bing Crosby’s recording made just weeks after the song’s stage premiere, that made it the galvanizing lament that defined the era. Based on a Russo-Jewish lullaby that Gorney’s mother sang to him when he was a child, it features both a minor verse and a minor chorus, with only a fleeting leap when lyricist E. Y. Harburg (The Wizard of Oz, “Lydia, The Tattooed Lady,” etc.) gives the protagonist a reminiscence of his days building the railroads that “raced against time,” before everything plummets back into a minor key and the reality of the country’s economic turmoil. Both Crosby’s version and Rudy Vallee’s somewhat more sprightly take climbed to number one before 1932 expired.

64.
TANK PARK SALUTE – BILLY BRAGG: This touching song written about the death of his father in 1976, when Bragg was 18, is a perennial favorite among his fans and can be found on his 1991 album, Don’t Try This at Home. The song’s circuitous and mournful melody provides the foundation for a searching conversation with his father, questioning, “what had become of all the things we planned?” and confessing, “there’s some things I still don’t understand.” The song proved hugely difficult for Bragg to write as he had largely avoided the subject of his father’s death until then, but he has noted that the song’s power to move people supports his theory that in order to write deeply affecting material “you must first articulate your own deepest feelings, those that are the most difficult for you to confront.” Though both the senior and (briefly) the junior Bragg spent time in military service, the “tank park salute” of the title seems to memorialize a private moment between a father and son that Bragg is rightfully keen to keep to himself.

65.
TROUBLE OF THE WORLD – MAHALIA JACKSON
Featured in Douglas Sirk’s 1959 Eastmancolor melodrama, Imitation of Life, “Trouble of the World” represents one of finest moments from the Queen of Gospel. Jackson pours every ounce of her soul into this universal message of release without ever slipping into unnecessary histrionics: “Soon we will be done / Trouble of the world.”

66.
THE ELECTRICIAN – THE WALKER BROTHERS
This disturbing, organ-chilled torture drama is the perfect mid-point between Walker’s two careers as brooding romantic in fab swinging ‘60s trio The Walker Brothers and his more recent work as an uncompromising iconoclast. The song’s obtuse lyrics likely refer to the United States involvement in Argentina’s Dirty War of the 1970s and early ‘80s, when many TK were imprisoned, tortured, and killed, and contains the frightening refrain “If I jerk the handle, you’ll die in your dreams.” Then from nowhere the middle eight blossoms into a gorgeous orchestral mirage—like a kick of hallucinogenic endorphins—before quickly disintegrating again into the same darkness it erupted from moments earlier, Walker explaining one more time in his shrouded croon, “When lights go low / There’s no help, no.” 

67.
CON ONOR MUORE (TO DIE WITH HONOR) from MADAME BUTTERFLY – GIACOMO PUCCINI
The crushing finale to one of the most performed and beloved operas in the world, Madame Butterfly. The libretto tells the story of Butterfly, a Japanese child bride who is abandoned in her homeland, pregnant, by her American sailor husband, Pinkerton. She gives birth to Pinkerton’s son and patiently awaits his return to Japan, but when he finally does return it’s as the husband of an American woman. Pinkerton’s new bride informs Butterfly of their plan to return to the United States and Butterfly implores them to take her son with them, and during this heart-rending final number, Butterfly tells her son to remember her face, sets him in the corner with a small American flag, ties a blindfold around his eyes before she disappears behind a screen and commits seppuku—ritual suicide—with her father’s knife. As she lay dying Pinkerton enters shouting her name: “Butterfly! Butterfly! Butterfly!”

68.
THE BAND PLAYED WALTZING MATILDA – THE POGUES
Written by folk singer Eric Bogle in 1971 to both honor the Anzacs (veterans of the Australian and New Zealand Army Corp.) and protest Vietnam, “The Band Played Waltzing Matilda” is a vivid, bitter first-person account of the horrors of war told from the view of a maimed Gallipoli veteran. It’s defining moment came when The Pogues recorded it for their 1985 album, Rum Sodomy, and The Lash, as Shane McGowan’s warbling vocal perfumes every line with well whiskey, giving a hard-won patina to lines like “I looked at the place where me legs used to be and thanked Christ there was nobody waiting for me.” The song famously blends Australian bush ballad “Waltzing Matilda” (a “matilda” being a backpack, not a woman) into its finale, as time passes and everyone forgets the sacrifice of the “crippled” and “blind and insane” soldiers who returned from the war.

69.
LONESOME TOWN - RICKY NELSON
Released in 1958, two years after Elvis Presley topped the charts for the first time with the conspicuously similar “Heartbreak Hotel,” Ricky Nelson’s ode to lost love is a lugubrious fantasy where teardrops are currency and everyone’s in the 1%. Written by Baker Knight—who also penned Nelson’s hits “Poor Little Fool” and the “Lonesome Town” flipside “I Got a Feeling”—this simple song is composed of the teen idol’s sugary voice, a delicately strummed guitar (which Nelson was proud to have played on the track), and what may be the most depressed Greek chorus in rock history—the sepulchral backing singers rising through the recording like disembodied voices from the bottom of a well. It climbed to number 7 on the U.S. charts when released and has since been recorded by Paul McCartney, Holly Golightly, Richard Hawley, the Four Preps, The Ventures, and Allen Clapp, among others, though the most notable re-interpretations have come from French chanteuse Françoise Hardy and shockabilly group The Cramps. If younger listeners know it now its likely thanks to its inclusion on the soundtrack to Quentin Tarantino’s Pulp Fiction.

70.
ON THE NATURE OF DAYLIGHT – MAX RICHTER
Inspired by Franz Kafka’s fragmentary Blue Octavo Notebooks, Richter’s 2004 release, The Blue Notebooks, features ten tracks that capture both Kafka’s personal struggles and his own sparse, “post-classical” style. Actress Tilda Swinton reads selections from the notebooks while the composer folds all manner of organic and electronic sounds together to create a romantic, subtly modern whole. Composed of long, ponderous melodic lines, crying violins laying over one another to create a rich sense of sorrow that recalls the celebrated and bleak adagios of Barber and Albinoni, Richter tags late Beethoven as the model for “On the Nature of Daylight”: “I’m looking for that incredible intensity and clarity, using the minimum amount of notes possible.”

71.
GOODBYE PORK PIE HAT (THEME FOR LESTER YOUNG) – CHARLES MINGUS: A mournful, bluesy lament written by tempestuous bassist Charles Mingus upon hearing of the death of his close friend, tenor saxophonist Lester  “Prez” Young, just two months before the recording sessions for his 1959 album, Mingus Ah Um, “Goodbye Pork Pie Hat”—later renamed by Mingus “Theme for Lester Young” when he reworked it for his 1963 album Mingus, Mingus, Mingus, Mingus, Mingus—became and remains one his signature songs. In 1979 Joni Mitchell composed words to the song in collaboration with Mingus for her album, Mingus, opening the song with the touching line, “When Charlie speaks of Lester you know someone great has gone.” Mingus himself passed away soon after the album was released.

72.
BLUE IN GREEN – MILES DAVIS
Pianist Bill Evans’ liner notes regarding this achingly slow “minimalist-cool” ballad from 1959’s landmark Kind of Blue—“a 10-measure circular form following a 4-measure introduction, and played by soloists in various augmentation and diminution of time values”—belies the extraordinary emotional understanding on evidence in the song. Of the legendary sextet aligned for Kind of Blue—Davis, Evans, John Coltrane, Cannonball Adderley, Paul Chambers, and Jimmy Cobb—all except Adderley perform: Davis’ muted, introverted playing is heartbreaking, Coltrane provides a brief solo full of brooding beauty, Evans is pure magic and closes the cut with Chambers’ bowed bass grieving just beneath the surface. Davis claimed to have authored the whole of Kind of Blue, but it seems clear that Evans was, at the very least, the song’s co-creator, a fact the pianist always insisted to be the case. 

73.
EVERYBODY HURTS – R.E.M.
A maudlin hit spurred by an eerie video partly inspired by the opening of Frederico Fellini’s 8 ½—“Everybody Hurts” was uncharacteristically direct for the group (they specifically targeted the song’s lyrics to the dramatic and less-scholarly teenager brain), which certainly helped its popular appeal. It became a top ten hit across Europe while it petered out at 13 in the States. 

74.
ADAGIO IN G MINOR – ALBINONI
On April 5, 1992 the first shots of the siege of Sarajevo were fired. The following month a mortar shell tore through a bread line, killing 22 people, an act of destruction that motivated cellist Vedran Smajlović to don his tuxedo and perform a daring act of artistic protest, performing Albinoni’s “Adagio in G Minor” every day for 22 days in the rubble of his besieged city, becoming known to the world over as the Cellist of Sarajevo. Tomaso Albinoni’s “Adagio,” overflowing with tearful remorse and lugubrious melody, was a gorgeous choice, but its likely that the piece was not written by Albinoni at all, but primarily composed by Italian musicologist Remo Giazotto after he discovered a few threads of unattributed notation (a full bass line and a few bars of violin) in the ruins of the Dresden State Library following WWII. Whatever its origins, the “Adagio in G Minor” is an enduring part of the classical canon and rivals Barber’s “Adagio for Strings” in its heart-swelling despair.

75.
BORROWED TUNE – NEIL YOUNG
Appearing on Young’s caustic and strung-out 1978 album, Tonight’s the Night, which was largely an attempt by the singer to exorcize the demons that haunted him following the deaths of his friends guitarist Danny Whitten and roadie Bruce Berry—“Borrowed Tune” (which was actually written before Whitten and Berry overdosed) is a spare ballad built on a fraying rope bridge of piano and harmonica. In a conceptual trick Young openly nicks a melody from the Rolling Stones’ “Lady Jane” (the “Borrowed Tune” of the title) admitting in his tired, nasal rasp that he’s “too wasted” to write his own melody. 

76.
RIVER – JONI MITCHELL
Appearing on Joni Mitchell’s 1971 masterpiece, Blue, “River” was never released as a single, but has blossomed over the years into one of her signature songs. Opening with a brief melodic nod to “Jingle Bells,” the song explores the need for change following the end of an intense relationship (Mitchell and The Hollies’ Graham Nash split just prior to her recording of Blue), Mitchell punishing herself for ruining everything, telling herself that she’s “so hard to handle,” “selfish” and “sad” and that she’s “made [her] baby say goodbye.” She wants to hide from everything around her—the reindeer, the “songs of joy and peace”—and longs for a frozen river she “could skate away on,” implying that the frozen river could be a metaphor for suicide—which Mitchell reportedly attempted just a few short years later following her break up with singer Jackson Browne.

77.
TWILIGHT – ELLIOTT SMITH
Originally titled “Somebody’s Baby,” recorded during Smith’s final, unfinished recording session, and released posthumously on From a Basement on the Hill in 2004, “Twilight” is a song haunted: by intimacy, by fear, and by the mystery of its creator: From the bed of distant crickets that opens and closes the song and the chopping, scraping acoustic guitar, to, not least of all, Smith’s lyrics—super-heated with self-loathing and regret—and his weak, trembling voice, as if he’s whispering into every listener’s ears individually. Every good turn is an omen of impending despair. A five-note synth lead that circles the song for a full minute (beginning to sound like a tape loop dirge) before giving way to Smith’s withered voice, who confesses, “I’m tired of being down,” but the admonition fizzles into the dusky atmosphere as he returns to his truth, “If I went with you ‘ I’d disappoint you, too.”

78.
THE COLOUR OF SPRING – MARK HOLLIS
Inspired by the exploratory minimalism of Miles Davis, Karlheinz Stockhausen, and Morton Feldman, former Talk Talk ringleader Mark Hollis labored over every nudge of ivory, every brush of percussion and every buzz of breath rippling through every reed on his eponymous 1998 solo debut. The album is a bleak masterstroke that exists sui generis and its opening track, “The Colour of Spring,” is a leviathan of restraint. Featuring only a dappling of piano and Hollis’s retreating voice—he pounces at each abstract lyric with a young romantic’s urgency and dissipates just as quickly—it’s hard to conjure anything except rain clouds as he sings of forgotten fates and bridges burned. These moments will never come again.

79.
CANTUS IN MEMORY OF BENJAMIN BRITTEN – ARVO PART
When English composer Benjamin Britten passed away on December 4, 1976, Estonian quietist, medieval music aficionado, and radio technician Arvo Pärt—who had never met Britten and had only recently discovered “the unusual purity” of the elder composer’s works—welled up with “inexplicable feelings of guilt,” which he poured into the mournful “Cantus in Memory of Benjamin Britten.” Edgar Allen Poe, in a poem dedicated to the myriad ringing bells he heard while living in New York, called, aptly, “The Bells,” writes of the pealing of funereal bells, saying, “What a world of solemn thought their monody compels!” and that’s exactly what Pärt achieves as the split string ensemble descend a minor scale timed to the slow, deep chiming of a single bell, ending with the final tolling note drifting into silence. 

80.
BLUE AND GREY SHIRT – AMERICAN MUSIC CLUB
“Blue and Grey Shirt”—from AMC’s 1988 album, California, is a devastating song that pries Eitzel free from the barstool only to find him reflecting upon the death of a close friend from complications resulting from the AIDS virus. Eitzel’s exhaustion comes through in the lyrics—“I'm tired of being a spokesman for every tired thing”—and in his gruff, laconic voice as he slowly works towards his conclusion: “now I just sing my songs for people who are gone.”

81.
STAY WITH ME – LORRAINE ELLISON
Though the pleading soul ballad “Stay With Me” has been covered by dozens of artists over the years—notably Bette Midler, The Walker Brothers and Duffy—it was Lorraine Ellison’s agonizing soprano that got there first and her intense 1966 recording remains untouchable. The song peaked at #11 on the R&B charts and proved to be Ellison’s only major hit, but her three gospel-touched albums for Loma Records—Warner Brothers’ R&B division—contain a number of stone cold classics and remain a powerful record of her astonishing talents.

82.
100,000 FIREFLIES – MAGNETIC FIELDS
In the earliest days of Magnetic Fields songwriter Stephin Merritt—now comfortably the barrel-voiced center of the group—relied on delicate singer Susan Anway to bring his forlorn arch-pop lyrics to life. Released as the penultimate track on the group’s first album, 1991’s Distant Plastic Trees, “100,000 Fireflies” is a twee gem that shines like aggressively polished onyx. Over a cheap machine beat and sparkling ostinato bells Anway spins a haunting twee opera in miniature about the sorrows of stringed instruments, suicidal notions, catching fireflies, crippling isolation, and doomed romance. Anway sings lines like the infamous opener, “I have a mandolin / I play it all night long / It makes me want to kill myself” with a crisp sincerity and when she sings “this is the worst night I’ve ever had” you’re apt to believe her. In a 1995 interview Merritt intoned his philosophy that music has less to do with catharsis and more to do with “making pretty objects you can treasure forever.” In this case he’s managed both.

83.
DEATH LETTER – SON HOUSE
In “Death Letter,” a ragged and dark blues written and performed by Son House, love dies without drama, without passion or foul play, it’s just here one night and gone with the arrival of the “death letter” in the morning. By the afternoon he’s traveling to view the body “on the cooling board” before watching the body being lowered into the grave, and, with the sun setting, a major depression grips him (“Minutes seemed like hours, hours they seemed like days”) and soon he begins to believe she is haunting him, before concluding that “Love’s a hard ol’ fall.” 

84.
THE KIDS – LOU REED
Reed’s 1973 loose song cycle, Berlin, about the doomed love of aggressively troubled couple Jim and Caroline, has gained a reputation as “the most depressing album ever.” The distinction isn’t unearned and one of the reasons for its continued prevalence is “The Kids.” “They’re taking her children away” is the first line and the song continues to run through a list of Caroline’s transgressions while Jim calls her a “miserable rotten slut” and finds that he’s happier “since they took her daughter” as Caroline has traded cuckolding for sever depression. As if it weren’t dark enough the song also features a chorus of crying children screaming for their mother who, by the next song, has committed suicide. 

85.
PRELUDE NO. 4 IN E MINOR – FREDERIC CHOPIN
A whirl of contradiction, dandy salon artist Chopin responsibility for changing the conversation about piano music as painstakingly crafted a breathtaking world of miniatures including nocturnes, mazurkas, waltzes, ballades, impromptus, and, of course, the 26 preludes, of which none is more celebrated than the No. 4 in E Minor. Less than two minutes in length, the No. 4 is an austere gem that flows with a halting, fragile and natural sorrow. Chopin disliked the idea that his works should be infused with biography, but its hard not to read his melancholy that exudes from the fourth prelude and the dour environment in which it was written: ill and alone, Chopin composed the piece during a disastrous 1838-39 winter trip to visit his lover, author George Sand, and her children. In Sand’s words, Chopin’s preludes, from their moment of conception, were “masterpieces,” which “present to the mind visions of the dead and the sounds of the funeral chants which beset his imagination.” Fittingly, the No. 4 was eventually played at Chopin’s funeral in 1849.

86.
I WISH IT WOULD RAIN – JOHNNY ADAMS
The melody was written by Barrett Strong on a $40 piano with ten working keys while the words were penned by introverted lyricist Roger Penzabene as a last ditch catharsis to heal the betrayals of his cheating wife, but “I Wish It Would Rain” became a major hit for the Temptations upon its release in December 1967, reaching #4 on the pop charts and topping the R&B charts. Unfortunately, Penzabene, unable to deal with the pain of his relationship, committed suicide on New Year’s Eve, just days after the song’s release, giving new gravity to lines like “With her went my future / My life is filled with gloom.” Though a number of artists have recorded the song, the release that best captures its broken heart is Johnny Adams’ 1972 version. The Tan Canary does away with the Temptations’ jumpy mid-tempo beat for a slow burning Black Moses vibe that positively simmers with pain. 

87.
WITHERED AND DIED – RICHARD AND LINDA THOMPSON
I Want to Shoot Out the Bright Lights (1974) was the first album from recently wed husband and wife duo Richard and Linda Thompson and is a bleak collection of English folk rock, the darkest cut of which is the sorrowful ballad, “Withered and Died.” Richard’s restrained guitar on the processional track leaves room for Linda’s despondent vocal—she once described herself as having “the soul of Ingmar Bergman”—as she explores themes of loss and betrayal, ending each verse with the tearful avowal, “my dreams have withered and died.”

88.
SAM STONE – JOHN PRINE
Though songs like Lou Reed’s grimy “Heroin” (1967), The First Edition’s “Ruby, Don’t Take Your Love to Town” (1969) and Scott Walker’s “Hero of the War”  (1969) all pre-date John Prine’s “Sam Stone” (1971) for shocking drug imagery or close-to-home, post-war tragedy, Prine’s line “there’s a hole in daddy’s arm where all the money goes” alone places the song alongside The Doors’ “Unknown Soldier” and Creedence Clearwater Revival’s “Fortunate Son” as a defining statement of the era. In a thin, nasal wheeze over a plaintive organ and crisp acoustic picking John Prine spins the caustic story of Sam Stone, a Vietnam veteran who comes home from the war with frayed nerves, “shrapnel in his knee,” and a gateway addiction to morphine. To absolutely no one’s surprise things snowball quickly, the foggy sense of an “overdose hovering in the air” long before Prine says it. It’s not long before Stone pops “his last balloon” and OD’s, leaving his family to sell their home in order to buy him a casket. The original can be found on Prine’s 1971 self-titled debut, but the song echoes in Pink Floyd’s “Post War Dream” (on 1983’s The Final Cut) and is more directly quoted in Spiritualized’s “Cop Shoot Cop” (from 1997’s Ladies and Gentlemen We Are Floating in Space).

89.
BLEMISH – DAVID SYLVIAN
Struggling for definition in the midst of his crumbling marriage David Sylvian created 2003’s Blemish, a work he has referred to as his most “unguarded,” and you can’t make it past the opening title track without understanding where his head is at. In his velour tremble, mixed front and center, he spills lines like “I fall outside of her,” “There’s no talking to her,” and “He who was first’s coming in last” over a tenebrous rippling of guitar drone—the chill is palpable and one can nearly see the curlicues of fog forming on his breath as he sings, “Life’s for the taking they say / Take it away.”

90.
THE SHORTEST STORY - HARRY CHAPIN
A passionate activist, singer/songwriter Harry Chapin dedicated a substantial portion of his earnings to fighting world hunger, and this brief coda to his bestselling 1976 album Greatest Stories Liveis a pungent attack on the evils of food insecurity. It is a heartbreakingly succinct inditement that it has been used in comments before Congress to illustrate the plight of the hungry. The song opens with a birth, but here the beginning of life is inextricably linked with the cruelties of the world as even the “promise” of the sun “burns.” Just a brief 20 days into life, the unfortunate child at the heart of the song is shunned by his mother as he watches a bird circle overhead and asks himself, “Why is there nothing more to do than die?”

91.
SUICIDE IS PAINLESS (THEME FROM M.A.S.H.) – JOHNNY MANDEL AND MIKE ALTMAN
“Suicide is Painless” originally appeared in Robert Altman’s 1970 film version of M.A.S.H. before it became more widely known as the theme to the long-running television series. Co-written by musician Johnny Mandel and Altman’s son, Mike Altman, the song became a UK number 1 in 1980 and has been covered by a host of artists, prominent among them is a version released as a single by the Manic Street Preachers in 1992, which peaked at No. 7 on the UK charts. During a Tonight Show appearance in the 1980s, Altman joked that his son made more than a million dollars in royalties from his part in writing the song, while he made only $70,000 directing the film that spawned it.

92.
FRUIT TREE – NICK DRAKE
For all the myth and mystery of Drake’s short life and premature death he does seem eerily prophetic on “Fruit Tree,” the penultimate track of his debut, 1969’s Five Leaves Left. His delicate, paper-thin vocal trembles over the lush strings as he ponders the fleeting warmth of fame (“Fame is but a fruit tree, so very unsound”), the quicksilver brevity of life, and the comfort of death (“Safe in the womb of an everlasting night”), but its his commentary on the power of posthumous fame that really sends shivers down the spine: “Safe in your place deep in the Earth / That’s when they’ll know what you were really worth.”

93.
KATY SONG – RED HOUSE PAINTERS
Found on Red House Painter’s first self-titled release of 1993 (Unofficially Red House Painters I or Rollercoaster), “Katy Song” slams together two rock buzzwords of the 1990s—slowcore (glacial pacing, reverb-soaked guitars) and shoegaze (nearly three minutes of dream-rock whirl)—into one gorgeous eight minute-plus miserable epic about the end of singer/songwriter Mark Kozelek’s relationship with his girlfriend and muse, Katy. Kozelek funnels his anguish into a sprawling ode to disintegration, singing with plaintive contemplation, “Can't go with my heart when I can't feel what's in it / I thought you'd come over but for some reason you didn't.

94.
WISH YOU WERE HERE – PINK FLOYD
Between the stunning talents of Roger Waters and David Gilmour Pink Floyd crafted a staggering number of melancholy prog classics through the ‘70s and ‘80s, including “Us and Them,” “Comfortably Numb,” “The Final Cut,” etc. and so forth, but “Wish You Were Here,” from 1975’s “very sad record” (Waters) of the same name, touches something more earthy, more human, and less political (not a-political), which allows it to hit that much closer to home. Waters described the song as “schizophrenic,” an accounting of “the battling elements within myself,” with some different lines being sung by different aspects of his personality. Book-ended by a haunting, existential, signal-from-nowhere intro and a post-apocalyptic windstorm effect that blows the song away, Waters’ raspy dualities interrogate each other before one finally recognizes they’re just “running over the same ground,” battling “the same old fears.” 

95.
SOUR TIMES (LIVE) – PORTISHEAD
It can be difficult to untangle Beth Gibbons’ bleak poetry—and her reluctance to discuss her work doesn’t help—but “Sour Times,” which first appeared on Portishead’s 2004 debut, Dummy, unravels with plenty of poisoned clues that point to the corroded love at the heart of the cut—the “hidden eyes,” “buried lives,” and “bitter taste”—but nothing in Gibbons collected works of cool despair hits like the crying refrain here; As she clings for dear life to her “memories of yesterday,” she summons the strength to tell herself over and over one truth every broken-hearted soul can understand, “Nobody loves me, it’s true.” Yet as wrenching as the studio version is the narcoleptic take that shows up on their 1998 live recording, Roseland NYC, really squeezes all the bitter juice out the song’s introspective turmoil.

96.
WHEN I WAS A YOUNG GIRL – BARBARA DANE
In the late 1950s guitarist and singer Barbara Dane lived at the intersection of the folk, blues, and jazz worlds. In 1959 alone she appeared on TV performing with Louis Armstrong and Gene Krupa, she released her debut album, Trouble in Mind, and recorded a series of traditional folk songs at the Ash Grove in Los Angeles with banjo accompaniment by Tom Paley. The Ash Grove recordings were released in 1961 as When I Was a Young Girl and her performances betray her wide-ranging musical interests as her husky, expressive voice is as powerful as it is fragile. The song, “When I Was a Young Girl” is a deathbed reflection of a woman who drank herself  “out of the barroom and down to [the] grave.” She calls for her parents to come sit with her and asks for wild roses to be tossed on her body then as she drifts away from her body she sees one final vision of “a young lady all clad in white linen” and as “cold as clay.” Odetta and Nina Simone recorded the song in the 1960s—two performers similarly unbound to clear genre distinctions as Dane—and, more recently, appeared on Feist’s 2005 release, Let It Die.

97.
HAVE YOURSELF A MERRY LITTLE CHRISTMAS – JUDY GARLAND
There are more than a handful of dour Christmas chestnuts, but “Have Yourself a Merry Little Christmas,” sung by Judy Garland, and taken from the 1944 musical, Meet Me in St. Louis, is the most miserable. The song’s original lyrics—which were written while WWII blazed across Europe and America’s involvement was still a question mark, opened with the line “Have yourself a merry little Christmas, it may be your last”—were scrapped after Garland and director Vincente Minnelli found it too depressing.

98.
MR. BLUE – THE FLEETWOODS
Mr. Blue was a number one hit in 1959 for soft-spoken doo-wop trio, The Fleetwoods. Written by Dewayne Blackwell, the song deals with decidedly risqué material for the squeaky clean group as singer Gary Troxel assumes the anxious identity of “Mr. Blue” while he watches his one true love “head for the lights of town” “on the sly” to prove her love “isn’t true.” It’s a genteel heartbreak, certainly, but no less painful for its simplicity.

99.
SYMPHONY NO. 3 (SYMPHONY OF SORROWFUL SONGS) – HENRYK MIKOLAJ GÓRECKI
Completed in 1976, premiered in 1977, and first recorded in 1978, it wasn’t until the 1992 release of Górecki’s Symphony #3 (Symphony of Sorrowful Songs) featuring soprano Dawn Upshaw that the confrontational composer became a member of the most exclusive musical club: a classical composer with a genuine hit record. Comprised of three separate laments, the Third Symphony broke into the U.K. top ten and capped classical charts on both sides of the Atlantic for months, a fact he tried to keep in perspective saying at the time, “the Górecki who is going through the 'shock' [of chart success] is of no interest to me.”

100.
THE SUN'S GONE DIM AND THE SKY'S TURNED BLACK – JÓHANN JÓHANNSSON
The final track on Jóhannsson’s 2006 conceptual IBM 1401, A User’s Manual—an album originally conceived as a modern dance soundtrack and subsequently re-invented—“The Sun’s Gone Dim and the Sky’s Turned Black” is a keening lover’s lament that pairs the final, fluttering goodbyes of early computer workhorse the IBM 1401 recorded in 1971—the music a sort of funereal performance by the very first computer imported into Iceland (in 1964) where, perhaps unsurprisingly, Jóhannsson’s father was its chief maintenance engineer—with mournful strings and the rippling sadness of a computerized voice that repeats in downward steps, “The sun’s gone dim and the sky’s turned black / Cause I loved her and she didn’t love back.” It’s a glitchy, sweeping ballad for the 21st century that touches on “ghost in the machine” themes as well as the same heartbreak-as-apocalypse found in Skeeter Davis’s “End of the World” and Edith Piaf’s “L’hymne a L’amour.”