The Ten Saddest Songs Ever

As Elton John said, there are times when we all need to feel a little pain. Or to be more accurate, Bernie Taupin said it and Elton just repeated it while playing a piano. But without getting caught up in who brutally kept who in obscurity while growing rich off whose talent, it is absolutely true that songs of the melancholy variety do indeed reach into your room —


And when all hope is gone, sad songs do say so much. Even when all hope isn’t gone, they go all right. So in honour of the greatest tearjerkers of the musical world, here (in no particular order) are the Ten Saddest Songs Ever. Drop me a comment to let me know what your saddest songs are.

Hamilton — It’s Quiet Uptown

The songs of Lin-Manuel Miranda’s musical juggernaut Hamilton take one through the whole gamut of emotions over the show’s running time, and there’s more than one moment of tragedy. But the real killer, the monumental emotional gut-punch calculated to reduce strong men to a blubbering mess is “It’s Quiet Uptown”. This crushing lament may end on a note of tentative hope, but the atmosphere throughout is one of pain and loss and the exhaustion of irrevocable sadness. The arrogant, ambitious Alexander Hamilton here is no soldier, no statesman, no political power-player. He is simply a bereaved father and regretful husband, “walking by himself, talking to himself” as he tries to come to terms with the actions that have led not only to the collapse of his marriage, but the death of his son. As Hamilton, Miranda’s voice cracks like a breaking heart as he sings of his daily routine in the hollow shadow of grief. The song hits hardest as Hamilton’s sister-in-law implores those who see Alexander to “have pity — he is going through the unimaginable”. “Unimaginable” is the only way to describe the idea of losing a child — a feeling so nightmarish that if it hasn’t happened to you, your mind simply cannot envision it — and that dread permeates every line of the song, even as it comes to a close with the glimmer of light offered by forgiveness.

Paul Kelly — How To Make Gravy

Paul Kelly has built a career on his masterly ability to tell vivid, concise stories that depict the excitement and pain of being human with compelling precision. In “How To Make Gravy”, he spins a yarn of near-unbearable agony that can leave a listener feeling positively bruised. Assuming the persona of a convicted criminal writing to his brother at Christmas, Kelly sings about how much fun the family festivities will be back home, asking the brother to “kiss my kids on Christmas day/please don’t let ’em cry for me”. Reflections on the family, the weather and the food, a plea to make sure the gravy is made right, and then…the breakdown. The narrator pleads for forgiveness, asks that his brother tell everyone that he’s sorry “I screwed up this time”. Kelly’s voice rings with scorched regret as he begs his brother to not “stab him in the back” with his wife, immediately backpedalling and apologising, but “the mind it plays up” in his position. He promises, once he gets out, he’ll make the gravy again: he swears “I’m gonna pay them all back”. Kelly has sung often and brilliantly of ordinary, downtrodden people fighting to carve out a corner of happiness in an unfair world, but here he reaches deeper than ever into fathomless reservoirs of pain, a plaintive cry for forgiveness and redemption from a man who fears he’s thrown it all away and doesn’t know whether he can ever get it back.

Five For Fighting — Superman (It’s Not Easy)

It’s a song about Superman. Specifically, about how hard it is to be Superman. Which sounds silly as hell, but somehow John Ondrasik’s wistful soliloquy manages to capture the loneliness and yearning of being a superhuman alien in a way that sets off something sorrowful and human within the listener. Suffice to say, the succession of directors who have brought Superman to the big screen can only wish they infused the character with as much emotional depth as this song does. Ondrasik’s Superman is all alone in the world, dreaming of “a home I’ll never see”, longing to find a way to connect with the people who see him as only a “pretty face beside a train”. Obliged to be the world’s saviour, Supes cannot show his fragility to the world. He’ll keep doing his duty, he’ll keep trying to find “the better part of me” — but it’s not easy. In the end, he’s only a man.

Johnny Cash — Hurt

Nine Inch Nails’ original version is shattering enough, a rising crescendo of self-loathing that punches you in the face with its total denial of hope. But Cash’s cover is something else. The stark musical backing leaves Johnny’s subterranean rumble to preach into the void a sermon of weary pain. If Trent Reznor’s rendition of his own song was a savage depiction of youthful emptiness, Cash presents it as the ultimate expression of regret for a life that, almost at its end, has suddenly been recognised as wasted and futile. Like an ageing gunslinger slumped in the dust, whispering his last words as he bleeds out, Cash sings, “What have I become?” in a voice like a crumbling mountain, gazing bleakly into the nothingness of existence. Johnny wants you to know that we all die alone, thinking only of what we’ve done wrong.

Suzanne Vega — Luka

Suzanne Vega noticed a boy called Luka among the kids who played in front of her building, who seemed just a bit different, a little apart from the others. She knew nothing about his life, but she used her memories of Luka as inspiration for this heart-rending portrait of an abused child. Luka lives on the second floor, trying not to “talk too loud” or “act too proud” to avoid the violent punishment of (one presumes) his parents. The whole song is sung from Luka’s perspective, as he pleads with his neighbour not to ask him what’s been going on upstairs (“I walked into the door again”), considers how he’s brought his suffering upon himself, and explains, “They only hit until you cry”. It’s a story all too familiar to too many of us, and Vega’s gentle, sweet voice is the perfect vehicle for this disturbing account of a lonely, frightened child who may never be rescued.

George Jones — He Stopped Loving Her Today

A lush, shamelessly sentimental ballad typical of the slick syrup that Nashville liked to serve up through the 70s, this is a cut above the average C&W tearjerker, elevated by its heartstring-tugging composition and Jones’s miraculous voice, deep and smooth and sweet and resonating in every syllable with the memory of a thousand loves lost. The lyrics are a shining example of the bittersweet irony that country always does so well — Jones sings about a friend who despite his love for a woman being unrequited, promises to love her till he dies. And he stays true to that promise, but “he stopped loving her today”. Jones goes around to his friend’s house to see his body, observing wryly, “This time, he’s over her for good”. Even by the depressive standards of the country genre, this song is an overwhelming bummer, but fortunately it’s also irresistibly beautiful. Other singers might’ve made it sound trite and manipulative, but with Jones’s golden throat, it’s simply gorgeous sadness. To hear him sing “First time I’d seen him smile in years” is to suddenly feel all the weight of the world’s tragic absurdity crashing upon you like a wave.

Dolly Parton — Jolene

Eighty percent of country songs can make you want to walk into the sea, so it’s no surprise more than one would pop up on this list. This is a simple song on a simple theme— another woman is coming to take Dolly’s man. In a Loretta Lynn song, this would be a trigger for a threat to punch that other woman’s lights out. Dolly, however, taps into the primal fear we all have of losing that that is most important to us. Jolene doesn’t love him, of course: if she steals him away, it will be “just because she can”. But she can have any man she wants, while Dolly knows this is her one and only. She also knows she cannot compete with Jolene’s intoxicating charms — all she can do is beg Jolene: please, please don’t take him. Every desperate repetition of the title is a plaintive cry of terror — Dolly knows that this plea is her only chance: if it fails, Jolene will come, and nothing Dolly can do will stop her. It’s the tragedy of the singer’s situation, mingled with the looming menace hovering over every line, that makes the song so mesmeric.

David Bowie — Heroes

Bowie weaves the tale of two lovers, on from the East and one from the West, meeting by the Berlin Wall, amid a background of driving percussion and howling guitars, his voice cutting through the wall of sound like a hymn sung in a hurricane. The sadness is tempered with triumph: “we can be heroes” qualified with “just for one day”, and that’s the mood that persists throughout, a defiant declaration of love in the face of all the world can do to defeat it, and an acknowledgment that that defeat is coming. The desperate sob in Bowie’s voice is perfect.

Simon and Garfunkel — The Only Living Boy In New York

It’s really just a catchy musical sulk. I mean, Paul Simon’s friend (if they even were still friends by this stage) left him to go make a movie in Mexico. Garfunkel was spreading his wings and it left Simon in cold NYC working on songs for Bridge Over Troubled Water alone. Why should anyone else care that Paul is lonely and bitter? We shouldn’t, but when Paul Simon sulks, he sulks exquisitely. It’s the gift of the great artist to make self-obsession seem universal, and this beautifully wistful tune captures the heartbreak of once-close friends watching the ever-expanding divide between them, and the gloom that can seem all-embracing when you’re by yourself and working non-stop and you’re sure that nobody loves you.

Sarah McLachlan — When She Loved Me

The Toy Story series of movies is full of boisterous fun, hilarious comedy, and cutting-edge animation. But its main purpose, most people agree, is to force adult humans to cry in public against their will. Toy Story 3 is a force of emotional destruction that Nicholas Sparks can only wish he could match. But the first two instalments do all right on the crushing despair front, especially when Pixar’s favourite songwriter Randy Newman is on the case. His “I Will Go Sailing No More” in the original Toy Story is the perfect melancholy accompaniment to the devastating moment when Buzz tries to fly and crashes, along with all his dreams and sense of self, to the floor. In Toy Story 2, he ups the ante with “When She Loved Me”, and the heartache is turned up to 11 by the song being handed to Sarah McLachlan to sing. Her silken Canadian pipes turn a desperately sad song into a real wrist-slitter. In the film, the movie accompanies the reminiscences of Jessie the toy cowgirl, as she recalls her happy previous life as the companion of a little girl who loved her…and then abandoned her. Pixar managed to make three whole films that caused millions of people to identify with the emotional crises of toys: in this song, the killer combination of Newman and McLachlan make us feel the unbearable pain of being a discarded toy, and it’s horribly familiar. Jessie’s pain is the pain of rejection and abandonment that every one of us knows — I need a hug.

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