Nothing quite cuts through the sunny disposition of an eternal optimist like a depressing song. Forget all the joy, happiness, peace, harmony and the rest of that shit that music inspires in listeners; those emotions are easy. When a song can make listeners sob softly or catatonically stare at their shoes and ponder life’s utter bleakness, that’s when a song is truly special. Whether it’s Richard Thompson telling a small child that there’s nothing at the end of the rainbow or Tom Waits asking us to hang down our heads for sorrow, we all have songs that affect us in a certain way. So grab the tissues and open up those tear ducts as Spectrum Culture’s staff presents their choices for most depressing song ever. – Eric Dennis


Mary Chapin Carpenter- “Other Streets and Other Towns”
from Hometown Girl (1987)

You only get to be disappointed in a handful of ways that really surprise you. It’s likely that Mary Chapin Carpenter has written a song for each one. “Other Streets and Other Towns” is about the time when you attached all of your young dreams to the coolest and dreamiest person you ever knew, back when love could be wild and feel new at every turn. Non-coincidentally; this is the one person who could never love you forever.

The last line of the main chorus is when the full impact of her song sinks in and becomes our story too: “My dream are largely lost and found on other streets and other towns.” Carpenter sings it in such a light and sweeping fashion that it takes a little bit of time for that to really sink in.

We still have hopes which are waiting by the porch light in an undefined and deeply nostalgic somewhere that’s created just to agonize over on lonely nights. At the same time, it’s true that most of us will grow up one day to be stronger and better at choosing who we let into our lives. “Other Streets and Other Towns” reminds us of a time when the stakes didn’t seem quite so high and the line between wide-eyed longing and real devotion was nearly invisible. – Neal Fersko


Mark Kozelek- “Ruth Marie”
from Rock ‘n’ Roll Singer EP (2000)


Pop music is so exceptionally good at describing the most minute iterations of adolescent romance that it’s easy to forget how much of life there is left. It’s hard to tell whether that’s because the songs about married life, child-rearing and familial loss are not being written (this isn’t the place, but at some point I’d like to write a piece about the band Truckstop Honeymoon’s seemingly unique continuing exploration of those messy joys), or that the audience for songwriters in and past middle age is some combination of nonexistent, too distracted to listen or not profitable enough to notice.

And so one’s first challenge when asked to consider “depressing” songs is to eliminate the small-t tragedies of romantic complication: any girl-group box set will reveal that a small army of anonymous professionals and hacks were mobilized in the early ’60s, like military contingency planners, to address any possible narrative concerning romantic coupling between the ages of 14 and 25, plausibility be damned.

And you know what? Those kids got over it. The girls in a Shangri-Las or Jan & Dean song sobbing uncontrollably over a dead biker boyfriend grew up and married a dentist.

I say this with affection, because I do consider myself something of a connoisseur of sad songs, and I get a great deal of comfort from them. And it’s no secret that Mark Kozelek, late of Red House Painters, sometime of Sun Kil Moon, is one of the great purveyors of congealed, lava-flow bummers – this is a guy who could, and literally has, record(ed) the national anthem as a dirge. “Have You Forgotten” was a staple of my college-age mixtapes, but further consideration reveals it to be basically a love song with an incongruous chorus, thus disqualifying to the task at hand.

Or – and this is where dumping Kozelek in the file labelled “Singer-Songwriter, Self-Pitying” gets complicated – you can read it as a love song to a troubled sister. Or even to the long-lost childhood friend of his earlier, charmingly homoerotic “Michael.”

I guess what I’m getting at is that you can almost feel his songs expanding outward, from first-person singular (“I’ve not been so alone, I thought, since kicking in the womb“) to first-person plural (“Letting someone into my misery“) to second-person concern (“Have you forgotten how to love yourself?“) – to the stop-dead third-person empathy of “Ruth Marie.”

It’s off the EP Rock ‘n’ Roll Singer, a funny throat-clearing after four years of silence and musico-legal issues; three AC/DC covers (prefacing a slightly underrated full-length of same), a John Denver song (post-facing a tribute album he’d organized of same), two pleasant originals and this: a song based (I’ve gathered, though I couldn’t say from where) on a visit with a girlfriend to her grandmother in a Midwestern old-age home, in the voice of the grandmother, in all its incurably injured pride, clinging need, resignation, remembrance, fear and, finally, love.

I grew so old in that house I lived in
They brought me here ’cause I can’t take care
I lost my worth and my purpose here
I feel you cry, but I can’t speak my mind
Will you hold me and never let me go?
‘Cause I hate it when you walk outside that door
‘Cause I know I won’t ever see your eyes
The eyes I gave you

It’s a unique song for several reasons, not least as a hospital drama in song: the only other that comes to mind is “Girlfriend In A Coma;” but that is, finally, more absorbed with the narrator’s reaction to the unnamed tragedy than it is with the subject, or even the doctor – or family? – to whom the tick-tock solipsism is addressed: “No, I don’t want to see her/ Would you please let me see her?

But it’s also an entirely believable voice two degrees removed from the songwriter: a degree of age and a degree of gender. I’m in no position to judge its authenticity – I’m neither aged nor a woman myself – but it feels right, down to the petulance, despite themselves, of the elderly at the blithe departures of the children for whom they’ve worked and sacrificed. And for a songwriter firmly from the lineage of self-involved male depression, in which women appear in lyrics form pretty much as cause or cure, this is a explicitly and exclusively women’s song – he’s decisively irrelevant, if he’s even in the room:

When my eyes shut, they’ll take me to the land
For fifty years I lived there with my man
And on my own, I lived for forty more
I watched you grow up from babies on the floor
To the beautiful women that you are
And I hate it that you’ve gone away so far

It’s a voice that rarely – unavoidably, and maybe by definition – speaks for itself in song. Aging and ordinary death are a natural concern of the novel (latter-day Roth, among many), film (On Golden Pond, obviously), even series-length television (Matt Saracen’s alternately loving and selfish grandmother on Friday Night Lights): it’s a long, deteriorating, universal and unavoidable story line, the tragedy of which is contained in its drawn-out inexorability and not easily expressed in a five-minute narrative. It’s still small-t, unromantic tragedy, maybe, because it’s so common, but I bet it feels just as raw, fresh, and helpless each time.

The evenings fall, they’ll drag me out the hall
Up to my bunk and drug me ’til I’m numb
But past the haze, I see your pretty face
Remember me when I’m gone
And know I love you, though I can hardly say
And I hate it when you see me in this way
But in darkness, I’ll always see those eyes
The eyes I gave you

– Franz Nicolay


David Sanborn- “For All We Know”
from Pearls (1995)

You know, the beauty of a depressing song is you never know the true meaning until you’re faced with a situation that reveals it to you. In the fall of 2005, I found myself falling into a deep and unforgiving depression. My days were spent in my room or out in my grandmother’s garden watching the world pass by. On the rare occasion, I would go out for a drive along the water on Highway 16, heading from Tacoma to Bremerton. For me, nothing beats a midnight drive. My life was beginning to manifest into an old blues song. The woman I loved and wanted to marry had left me. It was a time of vulnerability, a time of meditation and deep thought of what direction my life needed to go in.

I have always been a fan of David Sanborn’s work. Most of his successful albums were pop influenced jazz and what I call “funky 80’s jazz.” Though I’ve always had a special place in my heart for his Pearls album. I’ve always loved the ballad, “For All We Know,” though the meaning never appeared to me until that night. The song was written by J. Fred Coots and lyrics by Sam M. Lewis in 1934. Other famous version of the song have been done by Ray Charles, Dinah Washington, Nat King Cole, Rod Stewart and Roberta Flack.

The song opens with Sanborn playing a slow, powerful solo. Little Jimmy Scott begins to sing with his slow, sultry voice. His phrasing of the lyrics are perfect. His voice smooth, not overpowering the song in any fashion. “For all we know/ We may never meet again/ Before you go/Make this moment sweet again/ We won’t say goodnight/Until the last minute/ I’ll hold out my hand/And my heart will be in it.

The image that comes to mind when I hear the first couple of verses is the last night I spent with my girlfriend, Susan. Standing there on the porch in denial of what was to come. This was going to be the last time I saw her. I didn’t know it then, but I definitely know now. We stood there lifeless, not wanting to say goodbye. Knowing the longer we waited, the harder it would be.

I was driving like a mad man. I wish I could tell you how fast I was driving, but all I can remember is being entranced by Little Jimmy Scott’s voice. Johnny Mandel’s orchestral work frames the piece nicely around the vocal arrangement, with Sanborn chiming in with small, passionate interludes. The song ends with Scott belting out, “This may only be a dream/ We come and we go/Like the ripples of a stream/ So love me, love me tonight/ Tomorrow was made for some/ Tomorrow may never come/ For all we know!” It was in this verse that I realized that one can never truly wish love could last forever. I realized then, that I needed to make a new start. That life does go on. And I was right, a year later I met my fiancee, Emily.

“For All We Know” is an enchanting piece from start to finish that will have you re-evaluating old love, past mistakes and have you appreciate all you’ve gone through and obtained. – Andrew Cray


Okkervil River- “Savannah Smiles”
from The Stage Names (2007)

“Savannah Smiles” takes as its subject Shannon Wilsey, a porno actress who traded under the stage name Savannah. By 1994, after appearing in hundreds of skin flicks, she was dead at the age of 23, shooting herself in the head hours after an automobile accident left her with a broken nose and facial lacerations. Wilsey’s was a short and tragic life – her parents divorced when she was two years old, she had a miscarriage before turning 18, and large amounts of her porno dollars went to support her drug habit – and, all cynicism aside, consisted of the type of stuff ripe for lyrical interpretation.

In Okkervil River’s The Stage Names, an album whose inherent despair and sadness are largely offset by up-tempo and precise instrumentation, “Savannah Smiles” is its bleakest and most heartbreaking track, sung from the point of view of Wilsey’s father struggling to come to terms with the contrast of the daughter he thought he knew and the adult she’s becoming. In an album where somehow even a song about the suicide of poet John Berryman carries a tone of liberation, maybe even optimism, there’s none of that here. Singer Will Sheff assumes the father’s persona and sings in a world-weary and utterly defeated voice as he tries to reconcile the “baby doll” he knew with her far-different adult version. The father accidentally discovers his daughter’s diary – why he’s rooting around in her room at midnight and how he “didn’t know what it might be until it was open” are never explained – only to immediately regret his decision after reading only one page. We never find out what the father read, but it’s clearly nothing good: “Talk about your big mistakes/ Hey Shan, nice going” is all he can muster as he’s left staring at photos of his daughter when she was eight years old. There are, of course, “no tears in her eyes” in those pictures.

Sheff’s vocal approach and lyrics are enough to turn anyone into a sobbing wreck; even the fall sky is gray and the song on the radio offers no comfort, for chrissakes. What’s equally devastating is the song’s arrangement. Occasional guitar strums, strings, xylophone and what sounds like a ticking clock are subtly blended together to haunting effect. Unlike many of Okkervil River’s other songs, “Savannah Smiles” has no major musical highs or crushing lows; it just counts the days away slowly as the distance between the girl a father knew and the adult she is becomes greater and greater. Where portions of Black Sheep Boy could be faulted for being melodramatic, here the song’s restraint actually heightens its impact.

Certainly Okkervil River has recorded its fair share of ultra-depressing songs; “A Stone” and “Song Of Our So-Called Friend” immediately come to mind. Hell, Black Sheep Boy should have been packaged with a case of tissues so listeners could dry their tears as they listened to it. Still, with its pitiable narrator, tired vocals and mournful arrangement, it’s one of the darkest and most hopeless songs from this, or any, decade. – Eric Dennis


Henri Gorecki- Symphony No. 3, the Symphony of Sorrowful Songs

The first time I heard Henri Gorecki’s Symphony No. 3, the Symphony of Sorrowful Songs, I was driving from Washington, D.C. to my home in Annapolis, MD. It had been an extraordinarily long, difficult workday and I was tired of the hour-long trek between work and a real life. Hearing these Sorrowful Songs only exaggerated the how-sorry-I-feel-for-myself space I had been occupying. I almost pulled over to the side of Route 50 to blot my mascara-stained tears. This symphony was more powerful than any I had heard, but I attributed the depth of my feelings to, well, my feelings at the time.

The next day, I ordered the Symphony of Sorrowful Songs CD. I believe it was the Penguin Guide that advised that The London Symphony Orchestra conducted by David Zinman with Dawn Upshaw as the Soprano was the best at the time and I still believe it is. Just typing the title gives me chills and takes my breath away. By the time the CD arrived, I was not the maudlin person I had been on that tearful evening. With excitement, I cranked up the sound and sat in our living room to revisit an incredible memory of sound. Not two minutes into it, I was tearful again.

I marvel that any human can create such an incredible sound, this unearthly Symphony No. 3. A citizen of the Polish avant-garde during the 1950s and 1960s, Gorecki composed this masterpiece in three Lento movements toward the end of 1976 when he was in Katowice, Poland, and dedicated it to his wife. The four octaves and 27 minutes of the first movement highlights lyrics from a 19th century melody by Tatra Highlands folks musicians. In the middle, the soprano sings the Silesian folk song, “The Holy Cross Lament,” about a mother searching for her son who was lost in the Silesian Uprising.

The nine minute, second movement was composed around the words scrawled on the wall of a prison cell in Zakopane by an 18-year old girl, Helena Wanda Błażusiakówna: “Mother, please do not cry. Queen of Heaven, Virgin most pure, protect me always.” Gorecki noted that all the words etched into the prison wall were by prisoners who were justifiably angry and revengeful. Using the wall as an outlet for their frustration, they wrote words like “Murderers,” “Executioners.” Helena, on the other hand, was worried about her mother and longed to sooth her. Gorecki was fascinated by her selflessness and chose these words for this movement’s text.

Dawn Upshaw’s lament continues through the final 18-minute third movement depicting the voice of a mother crying for her dead son, the text of which may have dated from the First World War. The melody originated from Gorecki’s native Opole. The strength of tone, the power of wailing grief, the austere timbre of a skilled Upshaw, and the faithfulness to the original inspirations make these songs mournfully sorrowful. But perhaps, like Peer Gynt’s “The Death of Ase,” the slow and steady ascension of the notes provide not only the depth of feeling that accompanies sorrow but also a glimmer of hope.

If you crave “whole” experiences, abandon the notion of diet drinks, abridged novels and don’t listen to a truncated version of The Symphony of Sorrowful Songs. Schedule an uninterrupted 54 minutes that will transport you into another world where the separation of children from their mothers inspired music wrenched from the soul. – Jane Hruska


Björk- “The Anchor Song”
from Debut (1993)


One of many songs Björk wrote on a bicycle tour of Iceland in 1990, “The Anchor Song” was first introduced on Debut. Björk rode around Iceland visiting homemade church after church, playing the harmoniums most farmers had in her quaint but sincere Björkish way. This song’s eight lines make a concise statement: a description of someone diving into the ocean at night, “down to the bottom” and staying there as a “home.” This simple image haunts almost as much as the beautiful but quietly desperate counterpoint of the harmonium (or saxophones, depending on the version).

It’s certainly possible that the piece was meant as a simple personification of a literal anchor, dropping every night as a boat is buoyed until morning. But the lines “I dive into it… and drop my anchor” suggest a dropping of a dropping. I can’t help but picture Björk plunging underneath the waves, touching the bottom and dropping her anchor, entering a submerged hibernation and recharging each night in the quiet of the deep. The spatial play between harmony and melody is different than most of Bjork’s other rhythm driven work, and the result is a fragility that ironically weighs the song down, if you’ll forgive the pun. – Benjamin Bernstein


Nick Cave & the Bad Seeds- “Sad Waters”
from Your Funeral…My Trial (1986)


Apocryphal stories have Nick Cave, in 1986, riding the Berlin metro, writing lyrics in his own opiate-tainted blood, between nodding off. Be this fact or fiction, ’86 was certainly a bummer year for the Australian songwriter; one that found him continuing to use heroin; one he must have spent somewhat alone, doing the solitary work of writing his first novel And the Ass Saw the Angel, as well as one that found him easy prey for the unforgiving UK music press. Cave must have been feeling despondent, alienated, and entrapped by his own life, as the double EP that he titled Your Funeral…My Trial was full of songs full of characters full of extreme emotions brought on by prisons they’d been thrown into, be they figurative or literal.

This record, released after the all-covers Kicking Against the Pricks, found Cave recording what sounded like actual songs, in comparison to the bizarre mythological blues rants of his first two records where, save for a few exceptions, the Bad Seeds provided a jarring atmosphere than any musical accompaniment. We hear Cave solemnly stifle just how angry he is, falling for crooked women over and over in the title track, society’s misfits trample on through the mud, carrying the burdens of their status in “The Carny,” and in “Jack’s Shadow,” Cave visits the damaging psychosis inflicted upon a man in solitary confinement. The violence reaches an arresting boiling point on “Hard On For Love,” where Cave (like only he could) distorts Biblical symbols into double entendres, bound so tightly in chains of lust that any place other than inside a woman is the valley of the shadow of death.

The real magic comes after this disquieting half hour of music, after “Hard On for Love”‘s frightening singularity of intent. On “Sad Waters,” Cave seems to have a moment of clarity when he looks back wistfully at a past love. Singing “Down the road, I look/ And there runs Mary/ Hair of gold and lips like cherries,” he references “The Green Green Grass of Home,” covered by Cave hero Johnny Cash on his Live at Folsom Prison. Cave recalls a playful moment he and a love walked by a river, with the recording presenting a more sober-voiced Cave up front almost mournfully recounting the memory, whilst a second track of his voice sings more forcefully behind him as though it were the memories themselves, ebbing and flowing in the ether. From time to time, the two voices meet on the same word, as though some things are more vivid about this day than others.

While this tender moment is given splendorous treatment by Cave’s organ and Blixa Bargeld’s chiming guitar, Cave still makes mention of liberty deprived; even the root the lovers sit on is “bound” to the ground by ivy. Cave himself feels trapped by this memory of love likely lost, singing that he’s “forever a hostage/ Of [Mary’s] child’s world” and that he runs his “tin cup heart along/ The prison of her ribs.” Mary, carefree and perhaps ignorant to the powerful attraction Cave feels, goes wading into the water, turning it “into wine” by her very presence. Cave assigns her a kind of messianic status; she is the Lamb of God compared to all of “whoredom” seen throughout the rest of the record. Such tenderness must have been wildly out of character for Cave at this time, some 10 years before The Boatman’s Call. The song and therefore, the memory, begin to fade with Cave singing over aching organ chords: “Mary in the shallows laughing/ Over where the carp dart/ Spooked by the new shadows that she cast/ Across these sad waters/ And across my heart,” he, knowing full well that the shadow cast by this idyllic love now lost will haunt him forever. – Chris Middleman


The Mountain Goats- “No Children”
from Tallahassee (2002)

In 2002, John Darnielle created a concept album that would be a final testament to his ongoing “Alpha” series. Since 1991 the “Alpha couple” had shown up in tracks like “Alpha Desperation March” and “Alpha Double Negative.” But the entire Tallahassee album would be their final adventure together. In it, the couple moves into a house in Tallahassee, Florida and proceed to disintegrate and die in a fire.

But at what point is relationship is over? When the couple continues to exist out of habit? Where the line between love and hate is so blurred that they become one in the same? “No Children” could be the theme song. For one of the most depressing songs I know of, it is remarkably upbeat. With a spry piano part and walking bass line, although short, the pace is fairly quick. Darnielle’s strength has always been his words. Explaining in few words very complex ideas without too much exposition.

The husband acts as the narrator throughout the song and is constantly proclaiming everything bad he wants to happen to not only his wife, but also their relationship in general. Ruining the friendships they may have made with people that care about them. And attempting to destroy any support structure that may prevent or hinder their own destruction.

I hope that our few remaining friends
Give up on trying to save us
I hope we come up with a failsafe plot
To piss off the dumb few that forgave us

What gets me the most about “No Children” is the fact that the husband is so overwhelmed with emotion, he is not only calling for an end to their relationship, but truly wanting both of their deaths.

I hope you die
I hope we both die

I once heard Darnielle say before performing the song, “Sing this like you mean it, you might not mean it tonight… there will come a day when you’re gonna mean it.” With that, the entire crowd cheered, and enthusiastically launched into the song.

I am drowning
There is no sign of land
You are coming down with me
Hand in unlovable hand

Relationships are difficult. This isn’t a remarkable revelation, but the relationship between these two characters was so intense that with its destruction, neither have anything to live for. And isn’t that exactly what it feels like during a horrible breakup? – Nicholas Ryan


Damien Rice- 9 Crimes
from 9 (2006)

Damien Rice’s song, “9 Crimes” features Lisa Hannigan, thrusting her voice through ribcage and tear ducts as piano keys travel alongside her moaning of hesitant longing toward a new lover. She burns through words such as, “It’s the wrong time for somebody new/I t’s a small crime and I got no excuse.” As Damien Rice enters into the song, he breathes his deep sounds of denial regarding a situation of extreme lust and attraction between two people who feel the need to sing about what they shouldn’t be engaging in.

“9 Crimes” can be found on Rice’s second studio album, 9 and creates a haunting depiction of extreme attraction between two people who insist they are not the kind to cheat or stray.

Oddly, this song is featured in the computer-animated film, “Shrek the Third,” which I have not seen, and feel grateful to not have my illustrative depictions for this song ruined by a possible montage featuring an ogre and unconventional princess frolicking together.

I play this song on repeat when I want to fill a room with my sadness through intense instrumentation and the beautiful vocalization of Hannigan and Rice. I play this song when my own tear ducts are constipated, therefore must be forced out. I play this song when I am longing or looking to hear the sounds of it. – Aimee Herman


Bonnie “Prince” Billy and Matthew Sweeney- “Blood Embrace”
from Superwolf (2005)


First I ever heard Bonnie “Prince” Billy or any of his alternately melancholic or sinister songs about sex and obsession was in a parked car with the Oregon rain pouring down in an endless sheet across the windshield. The sky was completely ash gray. A friend and I were waiting for others to arrive, our plans completely ruined, and quietly he queued a song to play me as we sat in the confines of his old automobile. He told me he wanted me to hear something: “Blood Embrace” by Matt Sweeney and Bonnie “Prince” Billy’s collaborative album Superwolf.

Oh God, would I give her up to him/ If she told me he was better/ And that I didn’t have the chance?” From the opening lines, so full of the worst kind of jealousy and confusion, to the bitter marital dialogue from the 1977 film Rolling Thunder, the song chilled me. It seemed awful, and yet too terrible true to deny; anyone who’s ever suspected infidelity or felt the rage and pain of being second to some mysterious someone else could live by it. Since then, I’ve listened to Will Oldham range from the majestic to the quirky, but for me his dread has never reached the heights of “Blood Embrace.” I return to its spiraling guitar, its quavering vocals, its sheer gloom in my worst moments. Our friends eventually arrived through the rain, but I never forget how I felt the first time I heard it- like I was just gonna sit there, and listen forever. – Nathan Kamal


Cat Stevens – “Father and Son”
from Tea For the Tillerman (1970)


In nearly ever job I’ve ever worked, I worked with old men. Whether it was valet parking, janitorial duties, or hotel guests services, I’ve spent hundreds of hours hanging around small offices with guys in their sixties or older. Of course, there were guys my own age there too, but they were always the type who talked solely about relationship problems or party stories; neither of which I ever am a particularly good listener with and have little to contribute of my own. So I hung around the old guys. Jazz was my in. All these guys ever had to hear was I knew at least some music by Glenn Miller or Benny Goodman and they treated me like a boy genius. And in their defense, I look young. I fully expect to be carded in bars for the rest of my life. So for these guys to think I would only know Saturday morning cartoons really isn’t all that unfair.

Over time they began to open up to me about their families. Some guys were obviously more guarded than others, but the ones who had sons always seemed to feel comfortable telling me about problems they used to have with their boys; about their fights over religion, school, the military, drugs, politics and simple inherent misunderstandings from one generation to the next. And these old guys hardly had a thing to say about their wives, and could sum up forty years of working in the same place with no sentimentality at all. But they remembered specific conversations from decades ago with their sons with incredible fluidity.

Not surprisingly, it was my own dad who introduced me to Cat Stevens and specifically to the song “Father and Son.” I liked it when I first heard it, but it didn’t mean much to me. My dad and I have always gotten along. We go see shows, we go out to dinner, we try to take a trip together every summer; and so Cat Stevens’ lyrics about a strained paternal relationship didn’t hit home until I worked with the old guys. Stevens’ voice shifts between the characters much like the old guys told their stories. The father and the son became people I knew; I could give them faces; they had voices separate from Stevens’. Never had a song come alive for me like that. And I guess that’s why I think it is so depressing. Love songs are one thing, and they are great for pity parties. But those feelings can pass and people recover. With families, that’s the foundation of who you are. And at any given time there’s some kid who feels like he’s alone in knowing best, and there’s his father who can only look on while the kid falls with hostility into an avoidable mistake. Goddamn I think that’s sad. – Brian Loeper


John Prine- “Hello in There”
from John Prine (1971)

You don’t hear many songs about the elderly. You hear even less about the loneliness experienced in someone’s twilight years; in fact, taking a look over the pop music canon, you could be forgiven for thinking loneliness is something experienced solely by the young and misunderstood. But like Tom Waits, John Prine wrote and sounded like an old man even when he was young. It makes sense, then, that one of Prine’s greatest songs focuses on an old couple who have been left all alone; in some sense, it’s just Prine looking after his own.
Taken from Prine’s masterful self-titled debut, “Hello in There” is the songwriter at his best. Little more than gently plucked guitar and a metronomic muffled beat, with a Rhodes offering counter-melodies here and there, “Hello in There” is simplicity incarnate, its real powers stemming from Prine’s lyrics. Prine as a lyricist has always excelled at wonderful character studies, providing details piece by piece and trusting the listener enough to not completely spell anything out. Despite the Dylan comparisons Prine received at the beginning of his career, the two couldn’t be further apart; where Dylan trades in surrealist myth-building, Prine is a man of the people, offering messages that can be savagely witty or downright depressing, often both within the same song.

But “Hello in There” is almost exclusively the latter, the intent spelled out from the beginning by Prine’s narrator who states, “it’d been years since the kids had grown/ A life of their own/ Left us alone” before listing his children’s destinations, seemingly more out of an attempt to bring the memories of those children out from the dust-covered boxes they’d been left in than an explanation. Despite the fact that “old trees grow stronger/ And rivers grow wilder every day,” the narrator can’t help but notice that “old people just grow lonesome/ Waiting for someone to say/ Hello in there/ Hello.

It’s a tragic truth, spurred by everyone’s fear of becoming old themselves and thus closer to death and on its own it would be hard but tolerable to bear. But the type of pain Prine writes about is never so obvious and what makes “Hello in There” quite possibly the saddest song of all time is what follows. While it’d be hard enough to endure the loneliness of old age with your better half, our narrator confesses that he “and Loretta don’t talk much more/ She sits and stares through the backdoor screen,” indicating that Loretta has felt the impact of age more than he. The narrator thinks about calling up an old friend, but decides they wouldn’t have anything to talk about, since now life “just repeats itself/ Like some forgotten dream/ That we’ve both seen.”

And therein lies the message, the fact that we’re all repeating the same things and by the time we realize it, it’s too late. We all wind up alone and dying, but how many of us do anything to comfort those who already are? The tragedy of “Hello in There” is that its characters have seemingly been quarantined as a result of their age, their family and friends having basically abandoned them. And if the fact that old people are just waiting for you to drop by and say hello in there isn’t the saddest thing you’ve ever heard, I’m not sure I want to know what is. – Morgan Davis


Dar Williams- “When I Was a Boy”
from The Honesty Room (1993)


I’m no sap, but every time I hear the opening notes of Dar Williams’ “When I Was Boy,” a lump forms in my throat and by the last verse at least one tear is threatening to fall. On the surface, the song, is devoted to the weighty topic of gender roles as Williams reminisces about her tomboy youth and laments the current societal pressures of womanhood (like attracting and keeping a big, strong man). But at its core, the song is about childhood and the completely uninhibited and genderless way we lived as kids, something we sadly lose as we grow up, conform and abandon the freedom we enjoyed when we were girls and boys.

It hit home for me as the ultimate big-girl event – my wedding – approached. Staring at my white-gowned image in the mirror, a line from the song played on repeat in my head: “See that picture? That was me/ Grass-stained shirt and dusty knees/ And I know things have gotta change/…But I am not forgetting/ That I was a boy too.“The realization that I was actually a grown woman, when I still thought of myself as “a kid that you would like/ Just a small boy on her bike” was extremely tough to swallow. It reminds me that not too long ago, I didn’t care about what I wore or how I looked or really, what the future held. All I cared about was what could, as Williams sings, “help me climb a tree in ten seconds flat.”

It’s not limited to tomboys-turned-brides. Williams gets into the head of a guy as the song closes, and he confesses that when he was younger, “My mom and I, we always talked/…And I could always cry, now even when I’m alone I seldom do.” As I’m expected to doll myself up and “find a nice man to walk me home,” guys are expected to be manly men, not letting their guards down.

The song makes me remember that I’m a grown-up. When we were kids, we were all alike. We were all driven by our desires and our imaginations, not worrying about what people thought or where our lives were supposed to go. We did what brought us joy. Today, as bills pile up, deadlines loom and I’m bombarded by ads for pills and creams that will improve my appearance, this song is a sad reminder of the days when we were all on equal footing and all that mattered was that we were doing what made us happy. I was a boy. I was a girl. It didn’t matter back then. – Tara Pierson Hoey


The Velvet Underground – “Sunday Morning” and “Heroin”
from The Velvet Underground & Nico (1967)


“Sunday Morning,” the first song on the Velvet Underground’s1967 debut is deceptively simple and pretty. Like many great depressing songs, it disguises its dark, haunting lyrics with a hummable melody. It’s the rare opening song that feels like a closing song, chronicling the narrator’s slightly dazed walk home after a night of who knows what kind of debauchery. The chiming celesta and gentle bass line give the song an almost lullaby quality and Lou Reed sings in a slightly higher, ghostly voice: “Sunday morning/ Brings the dawn in.” Later he whispers in a slightly creepy/creeped out voice “Watch out/ The world’s behind you.” It’s a deeply paranoid song, one in which the narrator, on the stereotypically holiest and most relaxed of days, is in danger of completely losing himself and being crushed by the weight of the world, the wasted years, and his own inner turmoil. When Reed revisits the title, it’s “Sunday morning/ And I’m falling,” it’s the kind of song you listen to curled up in a ball on the floor. The band wouldn’t really explore their more vulnerable side again until their self-titled 1969 album.

“Heroin” opens the second side (on the record) and is brutal and explosive where “Sunday Morning” was intimate and composed. On the surface, it feels haphazardly assembled: drums that sound like overturned cardboard boxes, a few rudimentary chords, a seesawing viola (and no bass). Most listeners don’t have firsthand experience with the drug, but they don’t have to; heroin is used as what the late J.G. Ballard called an “extreme metaphor.” It’s a metaphor for utter desolation and psychological devastation, summed up in the first line, in which Reed, only 24 at the time, sounds unbelievably weary, dragging out the words: “I don’t know/ Just where I’m going.”

Yet there’s a yearning and desire for escape that gives it more depth than the average drug song (and this is the drug song to end all drug songs), as Reed feels like Jesus’ son and wishes he were a sailor 1,000 years ago: “Away from the big city/ Where a man cannot be free/ Of all the evils of this town/ And of himself and those around.” But he is constantly dragged back to the intense, somewhat surreal, Burroughs-esque world that he’s trying to shake-one of gabby politicians, mean people, mounds of dead bodies, and, of course, heavy drugs. As Reed starts to unravel, so the song speeds up and descends into a rather terrifying cacophony, as if it were trying to tear itself apart. That this came out during the height of hippie-dom makes it all the more striking.

Over 40 years later, little has matched the intensity of “Heroin,” even though Reed, who can have a sadistic relationship with his audience, continued into the heart of darkness, both lyrically Berlin and sonically Metal Machine Music. “Heroin” is an unrelenting epic of disgust with the world and psychic disintegration that leaves nothing standing-especially the narrator-when it’s over. And all Reed can conclude from this harrowing drug trip is “And I guess I just don’t know.” – Lukas Sherman


Leonard Cohen – “Famous Blue Raincoat”
from Songs of Love and Hate (1971)


In my experience, great things don’t happen at 4 am in the deathly cold of December. Judging by “Famous Blue Raincoat”, it appears Leonard Cohen agrees.

The elegant, spare production Bob Johnston uses to surround Cohen is pristine – desolate and cold, like the snow of the winter the writer has surrounded himself in. It leaves Cohen’s voice (drenched in reverb) and guitar to tell the tale of his doomed love triangle. As the singer writes a letter to an old friend, he reflects what that man’s affair has cost them all – Jane is “no longer anyone’s wife,” and the other man is “living for nothing now.”

Despondency lies in the helplessness and self-reflection the letter brings its writer – he can’t help but see the other man as both “my brother, my killer,” unable to forget the images of the evidence of his affair. He sees plainly that Jane is more at ease, if not better off – the pained look in her eyes is gone, the very pain the author had given up on relieving long ago. He’s haunted that it only took “a flake” of the other man’s life to do what he couldn’t, and considers it a personal failure.

Cohen’s delivery is frankly stunning, both naked and nuanced in all the right ways. He embodies the conflicted feelings he expresses verbally (to no surprise, since it’s an autobiographical song). He oozes venom when taking shots at the past, but seems sincere when he thanks his unnamed rival for standing in his way. Above all else, he’s exhausted.

Cohen has voiced some frustration with the song, claiming it was unfinished lyrically – too open-ended, and too abstract. It’s precisely this quality that makes it so affecting. The pains of love and trust are rarely one-sided, and never fully understood – they swirl inside your head, occasionally spilling out in the form of ink on paper. Or, in the hands of Cohen, a perfectly sad song. – Jason Stoff


Kenny Rogers and the First Edition- “Ruby Don’t Take Your Love to Town”
from Ruby Don’t Take Your Love to Town (1969)


Over a dozen artists have covered this Mel Tillis-penned song, including Leonard Nimoy and Right Said Fred, but it was Kenny Rogers and the First Edition who put “Ruby Don’t Take Your Love to Town” on the map in 1969, bringing to it the despondency of his vocal rendering and the band’s tender country angle. The lyrics of “Ruby” tell the true tale of a war vet with no choice but to sit back and watch his wife preparing herself for dalliances with other, more able-bodied men. He watches her gussy herself up for an outing as the evening sets in, and implores her to stay. That “crazy Asian war” (in Korea) has robbed him of the abilities necessary to met her earthly needs, but “it won’t be long,” he’s heard them say, “til he won’t be around” anymore. “If I could move, I’d get a gun and put her in the ground,” muses the coalescent, which makes for an extremely creepy, besides heart-rendin ditty. Not because we haven’t all fantasied about unfaithful lovers getting dead, but because Tillis wrote this song about a murder-suicide case in which a WWII survivor’s nurse-turned wife tested his mettle one too many times with other fellas.

The imagery of her painted lips, curled tinted hair and the dismissal with which the anguishing narrator is treated, along with its soft, instrumental cadence are what give this masterpiece its poignancy. “I still need some company,” he pleads, acknowledging that with his ‘bent and crippled legs,’ he can’t be of much use to her. But selfishness, that common symptom of those young and blessed with beauty, has her gallivanting off to town and leaving her infirm husband in the lurch of solitude. Between Rogers’ convincingly defeated voice and the collective awareness of being deserted, this tear-jerker is engineered like some old photograph of a well-loved traitor. Maybe you should retire it to the sob-stained annals of a past life… but once it does its circulatory rounds, and disperses all that hope and hurt and you’re back to wallowing in just how good bad can feel. – Joan Wolkoff


Pink Floyd- “Vera”
from The Wall (1979)

Though it may seem passé now, one of the most devastating listens is the first four songs of the third side (or second CD) of Pink Floyd’s The Wall. True, the rest of The Wall is an album about passive child abuse, the loss of a parent, emotional disconnection from the rest of the world, walled off dreams and the implosion of the ego by the dynamite of self-loathing, the run of songs kicked off by “Hey You,” mark not only the emotional epicenter of the double album, but the scared child lurking behind the terror of the wall.

Roger Waters created a story about a rock star who is utterly crippled by his neuroses; yes, “Pink” spends most of the album blaming women, his mother and past lovers, for his problems, but as the “wall” crumbles down at the end, Pink’s world is filled with sounds of his childhood and he spends his insulated days couched in the inculcation of television and other tools of flaccid self-destruction. It is obvious that this Pink, and possibly Waters by extension, feels unlovable and rather than let this supposed cold world destroy him, he freezes it out first with epic fits and then by lashing out at those who love him. “Can you feel me?” and “Would you touch me?” he flails out during “Hey You.” But it’s too late by this point since the wall is too high and there is respite for the emotionally weary.

Though “Is There Anybody Out There?” with its intense arpeggiated strings and the litany of self-hatred “Nobody Home” follow “Hey You”, it’s the emotional wallop of “Vera” that clinches this depressing run for me. On a topical level, the song is about British singer Vera Lynn, who hosted a program on the BBC named Emotionally Yours during World War II. Since the death of Waters’ father during the war is also a major theme of the album, it seems appropriate that he brings up icons from that era.

Once again, the sounds of television and an explosion begins “Vera.” “Does anybody here remember Vera Lynn?“asks Waters in a plaintive quaver. Sympathetic violins follow as he continues, “Remember how she said that we would meet again some sunny day?” The film version of The Wall begins with Lynn singing “The Little Boy That Santa Forgot,” which includes the lyric, “We’ll meet again, Don’t know where, don’t know when, but I know we’ll meet again some sunny day.” At the heart of this song is a scared little boy, waiting for that sunny day when his daddy comes home.

But the second half of the song, after the gentle musical break is when the really sad part comes in. Waters delivers, “Vera/ Vera/ What has become of you? Does anybody else in here/ Feel the way I do?” in such a heartbreaking warble, voice curling the “As” in Vera’s name, as the syrupy strings drive the point home. He is unable to recognize that he is not alone in his pain, that he is not completely untouchable. That self generated isolation is the biggest tragedy of all.

Sure, “Vera” is a song about a father who does not return from war, but it could also stand as a paean to unrequited love. There are certain connotations, certain connections we all make that allows a song to penetrate our psyche. For me, this song is the soundtrack to a broken-hearted young man on a July day, crying on a train in rural Spain. The air-conditioning is not working and his car is rippling with heat waves. Does anybody but him remember his tears on that sunny day? Probably not. – David Harris

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