Twenty Great Sad Songs

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Oh no, sad music? Here we go. We’re not trying to ruin your day, we swear. No matter how much we deny it, we love dejected tunes to shed good tear out on. In fact, it’s salubrious to listen sad music, in our lows or highs. There’s a late night moment, typically before bed, where that one Radiohead song comes on. You may tie a negative memory to the track, yet you listen.

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After break-ups, loss or any genuine reason to lose your shit, these songs are the soundtrack to our griefing, self-nurturing or just a flat out excuse to cry. A late night drive home and the song you tie to a bad period of my life comes on your phone or iPod (yes, have sad music on your devices, keep your options open) yet you don’t cry, it’s oddly refreshing to hear the tune that could make one ball in darker times.

The singer/songwriter gets you, or just gets close enough to match your morosity. They may hurt, cut deep or rehash the wounds of old, but at the end of it there is a cathartic feeling after listening to a musician’s woes, and, holy fuck, do musicians have woes. They’ve been dumped, beaten down or lost things you can not even begin to imagine losing. Some of the greatest music made is based upon tragedy or depression. The conflicted and defeated have graced us incredible music born out of their hearts, or maybe the ashy pile that once was.

Are you reading this because you’re sad? We may not offer much in the way of making you feel better, but we can provide 20 great sad songs written from the 1960s to now to help you out, or make you worse. Either way just get lost in misery and, dare we say it, enjoy. – Music Editor Kieran MacIntyre

Ethan Goodman

Elliott Smith – Waltz #2

A list of sad songs is guaranteed to play host to at least one Elliott Smith tune, but rather than taking advantage of his earlier, miserable anti-folk, I’ve opted to showcase one of his most gorgeous studio efforts. “Waltz #2” (XO) boasts Smith’s careful arrangement of guitars, strings and pianos, and while his numerous verses may ramble, they’re filled with heart wrenching lines that, while not directly depressing, find sadness in their deadpan observations. “She appears composed/So she is I suppose/Who can really tell?” The song’s sorrows are held in Smith’s frail voice and the apparent emptiness of the characters featured. “She shows no emotion at all/Stares into space like a dead china doll” hints at the hurt hiding just beneath the skin, which affects the listener far more than your average sob story ever could.

Wilco – Radio Cure

With just a heartbeat of a floor tom and a half strummed acoustic guitar to hold the song together, Jeff Tweedy opens “Radio Cure” with the simple, pained words “Cheer up/Honey I hope you can.” Immediately, we know something’s wrong, but we have no idea what it is, making it all the more terrifying and relatable. His tortured, hopeless whimpers whine on as weird clicks and white noise spit at the listener through the right ear before the chorus chimes with its simple toy piano melody. This minimal masterpiece is a progressive, atmospheric build, with each layer of gently plucked guitars, keyboards and a drum loop adding a new sheet of melancholy until it hits its breaking point, falling apart with the opening lines “Cheer up/Honey I hope you can.”

Jimi Hendrix – Castles Made of Sand

After all the ambiguity of the previous songs, let’s have some concrete examples of life’s sadness, yeah? In “Castles Made of Sand”, Hendrix gives us three stories encapsulating life’s bitter ironies in under than three minutes. He wastes no time, giving us tales of heartbreak, war and disease. Each one is more depressing than the last, breaking it up with the beautifully simple metaphor that makes up the songs title. The lyrics are potent, simple and heart wrenching, weaving woeful verses while leaving enough room for Jimi’s signature fluid, reverse guitar flourishes and clean chords. It’s a defining moment in Hendrix’s short career, providing the perfect balance between his impeccable songwriting and his musical virtuosity.

Apples in Stereo – The Silvery Light of a Dream (Pt. II)

If you’ve ever experienced a major loss, this song is required listening.
Robert Schneider of Apples in Stereo (who you can read about here (http://www.monstersandcritics.com/nostalgia-bomb-the-elephant-6-recording-collective-ten-essential-tracks/) in my previous article) turns textbook pop structures and simple rhymes into a cathartic examination of the grieving process. The childlike simplicity of the song is where the real pain lies, with lines like “Why die/I don’t understand it” underlining the agony of uncertainty. As we can see from the previous songs, the strongest sorrows stem from reality, and the following lyric “I try/but I feel dissatisfied” is far more familiar, and consequently more depressing than the melodrama of The Cure and those gothic romantics from the 80s. As a whole, the song is uplifting, with a flawless pop production featuring a perfect arrangement of guitars, piano, saxophone and Beatlesque backup vocals, padding the lines “I know now I have to be strong/I know now I have to move on.” It’s perfect pop rock, beautiful and emotive with killer guitars to boot.

The Beach Boys – I Just Wasn’t Made for These Times

With Pet Sounds, the manic-depressive Brain Wilson shied away from songs about summer flings, sports cars and pretty girls, instead creating a lush and somber record with some serious emotional depth. The title amplifies the feeling of being out of place and rings especially true for Brian, who was musically years ahead of his time. As a recurring theme in this list, we find that a glimmer of hope, dissatisfaction and simplicity make for the saddest songs, and Brian Wilson hits all three in a few short lines. The chorus is as basic as can be, repeating the words “Sometimes I feel very sad/Can’t find nothing I can put my heart and soul into,” a statement more vicious and painful than anything a thesaurus could come up with. The tuned percussion and electro-theremin solo back-up the title, and the dense arrangement provides some solace to the mournful tune. It’s an elegantly tragic track that encapsulates feelings of isolation without depressing the listener; a standout song on an incredible record.

Kieran MacIntyre

James Vincent McMorrow – Cavalier

If anyone knows how to do sad right, it’s the Irish. Their history is a painful one, religious divide that caused violence spanning over centuries and independence won on the loss of many lives. James Vincent McMorrow captures a lot of that pain in his music, though mostly from personal experience but the influence is there. This single from his 2014 album “Post Tropical” is a soulful meditation on losing his love; he remembers his first love and goddamn you will too when his impossibly high falsetto comes when he delivers those words. The song is sweet as honey with keys, subtle harmonies and McMorrow’s mellifluous vocals but it’s the ending in it’s bombastic explosion of horns and drums that the tears really come. The outro, rife with “Oo’s” and broken instrumentation descending into the void sting the heart but after it all, you feel release. People often make allusions to Bon Iver when talking about McMorrow, which is somewhat of a disservice because he writes incredible music that reflects a meticulous examination of his emotions and has irreproachable talent to match.

The National – About Today

Cincinnati based outfit The National capture all the best elements of Post-Punk, 90’s Alt and Country in their songs. The awesome instrumentals of their songs are brilliantly anointed with Matt Berninger’s monotone vocals, which have shed a tear from this writer in the past. “About Today” is born out of most painful part of a relationship, the numbing distance zeroth to the break up. Those painful moments where you feel the one you love is slipping away, you feel completely helpless as they drift. An unexpected breakup pales against the one you see coming, the dread of loss is only outweighed by the disappointment of trying to make it better and failing. The muted percussion carries a beautiful motif of guitar and Berninger’s one line at a time delivery of soul crushing words, built upon trying to save what he had. This is probably the saddest track in their body of work, yet it is my favorite, because it seizes my heart any time I hear it, who can blame me, this song is beautiful and leaves a long lasting feeling you can’t just shrug off.

Against Me! – Eight Full Hours of Sleep

The closer off Against Me!’s incredible “Reinventing Axl Rose” album is one of the most punk rock lullabies of all time. What Against Me! did best with this album and their earlier material was capture the punk aggression, but gave it sharp austerity. This somber tune features a acoustic guitar and passionate vocals from a then Tom Gabel, before she came out as trans (now her name is Laura Jane Grace), she tells you about what sleeping can protect us from: hunger, alienation, or the fears we have of the world falling apart; It doesn’t matter when we’re asleep. Our dreams can be the only safe place from the things we are afraid of, so we crave to go to the place where nothing can bother us. The dull feedback behind Laura and her guitar never lets “Eight Full” feel too quiet, a xylophone pops in for the chorus to give her words of the sun rising an espy of positivity. The song feels peaceful like a lullaby, but the lyrics shine stark reality upon the anxieties we have, which, sometimes, sleep can’t make go away.

Bill Withers – Hope She’ll Be Happier

This track from Bill Withers’ seminal “Just As I Am” record from 1971 can make even the meanest bastard shed a tear. Withers’ golden vocals are a pillar of R&B, here at their best, he reflects on a love he lost and wishes her the best with bittersweet sincerity. Every wonderful inflection in his melody are as clear as water, yet the thought behind his song is opaque with sadness. He wishes well, but him, he’s very far from okay. Anytime this song comes on, the mood can immediately change, but not always for worst, there is beauty to be found in his pathos. This song is ball-your-fucking-eyes-out material, let’s be honest here, but Withers’ euphonious voice transcends “Hope She’ll Be Happier” above any “poor me, got dumped” song. Whoever had the gall to hurt him, gave him an impeccable song that he sang with fervor unmatched even to this day.

Roxy Music – Avalon

The titular song of Roxy Music’s eighth and final album “Avalon” is like a slow dance in a burning building. Miles away from the Brian Eno era in it’s sound, this is where the party ends, but Bryan Ferry sings on. The over the top vocal harmonies, withdrawn back beat and Ferry’s smooth as butter vocals make this song feel like a rich Belgian chocolate, yet it doesn’t feel all too happy. “Much communication in a motion, without conversation or a notion.” Ferry delivers with lounge ease, this song doesn’t dig too deep but where it does dig it strikes upon gold that can leave you with the feeling of disconsolation. A listless dance number that feels more apocalyptic than it does romantic. Though there are stronger albums in the Roxy Music catalog, like their 1973 masterpiece “For Your Pleasure”, this song was a real treasure of their later albums, which also reminds me why Bryan Ferry is still among the greatest singers of the last century and still can break hearts today.

Anthony Augello

Nick Cave and the Bad Seeds – When I First Came To Town

This song is the sixth song off of the album “Henry’s Dream”. Nick Cave was apparently unsatisfied with the mix of the album, however overall I find it to be far better than merely listenable. “When I First Came to Town” has a somber Western tone to it, conjuring up images of a man dogged by his past shortly after arriving in a place that doesn’t know him and being rejected for it. The lyrics and Nick Cave’s deep, bitter, brooding, and dark vocals draw us into the dreary pain the man is living with as the instrumentation builds and builds into a crescendo with the narrator damning himself and vowing to return to the town one day and “see how quickly the tables turn” before the final chorus which lets the listener off softly at the end.

Echo and the Bunnymen – Killing Moon

Cult movie fanatics will recognize this from one of Jake Gyllenhaal’s early films, Donnie Darko, although the song predates the film by at least a decade. Off of their fourth album, “Ocean Rain”, it flips Elvis’s “Blue Moon” on its head, although perhaps not intentionally, by filling in the end of the story of that relationship that had begun in the song by turning it into a tale of loss where fate comes between the two lovers. Very fitting for the movie, whoever chose the songs for Donnie Darko really knew what they were doing. Ian McCulloch’s sorrowful and soulful vocals bring out every nuance in his lyrics. The string tracks and expert layering of the mix really bring the whole dark, woeful and beautiful atmosphere of the song together.

David Bowie – Heroes

What is more somber, romantic, and existentially-heroic than kissing in front of the Berlin Wall in 1977 in a doomed relationship? With the entire world crumbling around oneself as the world’s superpowers posture and threaten to destroy the entire world with that very wall as the obvious front line of the battlefield in the impending 3rd World War that is always minutes away on the Doomsday Clock, there can’t be anything much better than that. David Bowie and his masterful lyrics and the mind-blowing wall-of-sound he and Brian Eno teamed up to create for his album of the same title that was recorded at Hansa Tonstudio in what was then West Berlin perfectly captures that time and place and the feelings many must have felt there. If only we could all kiss as though nothing could fall.

The Skulls – Monet

The Skulls were originally a band that played at the Masque, the first Punk Rock club in Los Angeles in 1977 that the Germs, the Go-Gos, FEAR and countless other bands played many of their first shows at. They reformed in the early 2000’s with Billy Bones, the original singer and for the most part a new line up since most of the other original members were either dead or not playing music anymore and started putting out new music. This song came in at number 6 off their second album in this incarnation, the Golden Age of Piracy, and is a somber and soulful yet tough punk song with one of the catchiest choruses in all Punk Rock.

Suzanne Vega – Luka

Suzanne Vega’s “Luka” is one of the greatest pop songs ever written. She wrote sweet folk songs and her highest charting song in the United States was this song which is written entirely about and from the point of view of an abused child. No one in pop was doing that at the time at all. It’s a pretty heartbreaking song. Whenever Luka is talking to someone, he is always “running into doors” and he definitely doesn’t want the listener to pry into any of his home-life, just don’t ask him about. It’s hard to come across pop songs that have that kind of depth and we can only be told how great we are the way we are so many times by so many different artists. Overall it’s a beautiful dark song and Suzanne Vega’s lyrics and melody are sweet and simple and catchy, exactly as a good pop song should be.

Bella Elbaum

The Smiths – Asleep

First things first. I am not a Morrissey fan. I think The Smiths are a fantastic band, and Johnny Marr is an excellent guitarist, but Morrissey’s voice makes me want to gouge my eyes out. Yet, I find myself having a soft spot for “Asleep.” Morrissey’s voice is not quite as whiny, and works well with the melancholy piano. Many of Morrissey’s lyrics are typically depressing and he sings a lot about the world he lives in, and how much loathing he has towards it. This song touches on suicide and leaving this world behind, and going off to a “better world.”

The Velvet Underground – Pale Blue Eyes

The Velvet Underground were one of the first songs that I felt I had an emotional connection with, and lyrics that I could relate to, and this song was one of the first ones that just clicked for me. Lou Reed has many different songs, ranging from talk of prostitutes to drug abuse. “Pale Blue Eyes” is one of the more simple and more easily relatable songs. It’s a love song, and he expresses in simple words that still use imagery the love and emotions that love brings about. The soft tambourine in the back against his sing-talk voice, makes it even more soothing than any other Velvet Underground song. His twist of the expression “love hurts” when he says, “sometimes I feel so happy, sometimes I feel so sad” makes some people feel a little better. There’s going to be hard times, there’s going to good times. With that lyric he overlooks the fact that people think that with love comes pain. He regards that although there is pain, the good things will outweigh it.

LCD Soundsystem – New York, I Love You But You’re Bringing Me Down

Ah, a beautiful ballad of both love and hate for the beloved city that James Murphy of LCD Soundsystem lives in. The song starts off slow and dreamy, and building up to a cacophony of instruments and James Murphy passionately belting his confusion on whether or not he will be a loner living in this vast city of his. Murphy’s love/hate relationship with New York is a direct result of the changes that New York has gone through, and the corporate/business world it is becoming, which is exactly what Murphy has always tried to avoid.

The Brian Jonestown Massacre – (David Bowie I Love You) Since I Was Six

Brian Jonestown Massacre’s lead singer, Anton Newcombe is similar to Lou Reed in the sense that he did a lot of heroin, and was an incredibly talented musician who struggled through all kinds of problems throughout their lives. The songs are dark and twisted and touch on matters that sometimes many people cannot relate to. This tune opens up with “Does she love you, you suppose.” Newcombe is assuming that whoever or whatever it is that he feels so impassioned by hopefully feels the same way back.

The Flaming Lips – Waitin’ For A Superman

Wayne Coyne brings up back down to reality with this song, and let’s us know that sometimes life gets too hectic and crazy even for the strongest of people. Coyne’s voice consoles the listeners and makes you still feel like, even if thing do get “too heavy” we can work on through those problems. Coyne drops in a few weird kitty cat alien behind the piano that help you see the fun and silliness.

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