
25.Song:Masters Of War
Artist:Bob Dylan
Album:The Freewheelin’ Bob Dylan
“Like Judas of old/ You lie and deceive/ A world war can be won/ you want me to believe”. Bob Dylan is a man who was called the voice of his generation and despised that fact. It’s as if he, with all of his considerable lyrical talents, foresaw that his words would be a clarion call for every generation after, not an anointed brood by virtue of being lucky to be born at a particular time and amidst particular circumstances. If we live in a “World of Wars” as Foreign Policy magazine puts it, then Bob Dylan’s “Masters Of War” should be the background accompaniment to every decision, by every politician responsible for dragging us into the mire. It’s not enough that we, the people, must bleed for the greed and egos of others. They have to know that there’s only so much blood to give before the people return their affections in kind. “And I’ll stand over your grave/ ‘Til I’m sure that you’re dead”.

24.Song:Juicy
Artist:The Notorious B.I.G
Album:Ready To Die
“Super Nintendo, Sega Genesis/ When I was dead broke man, I couldn’t picture this” This is one of those rare great songs that immediately dated itself upon release, only to still sound effortlessly eternal. Puff Daddy had the right idea about wrapping Biggie Smalls rhapsodic verse with soulful vocal harmonies and bouncy bass lines, managing to add in his own voice as scattershot aural wallpaper. Tapping into such rich musical veins simply allows Biggie’s lines to reach aspirational heights that were rare in the gangsta rap days. He is truly a powerful voice, his rhymes flowing with precision that belies his booming presence. “I never thought it could happen, this Rappin’ stuff/ I was too used to packin’ gats and stuff” While bling rap would take the materialist urges of this song to their logical limits, Biggie Smalls dared to dream large, and for five glorious minutes, we could all dream along with him.

23.Song:Ain’t No Sunshine
Artist:Bill Withers
Album:Just As I Am
“Ain’t no sunshine when she’s gone” sings Bill Withers, the accompanying guitar strings creaking almost to the point of breaking, like a fragile promise. Stark, unforgiving, even the guitar player, one Stephen Stills, lending some light percussion to the proceedings has the effect of leaving Bill stranded, alone, dealing with the kind of heartbreak that only becomes harder to take as time passes. It’s incredible how much raw emotion Bill wrings out of every syllable, crystal clear in the mix even when the orchestra comes in. When the parade of “I know”’s come in, you get the feeling that, even when he is acknowledging the incredible emotional pain he is in, he can never fully take that leap needed to move forward. At 2:06 long, here is a song that packs its emotional punch into a compressed timeline, saying all that is possible to say when one finds themselves without anything left to hold onto. “Only darkness every day”.

22.Song:Smells Like Teen Spirit
Artist:Nirvana
Album:Nevermind
I want you, the reader, to recontextualize “Smells Like Teen Spirit”’s appeal in the vein of young people not having easy access to full lyrics sheets, or even the crystal-clear audio equipment and streaming available to us today. You are a teenager or young adult in the early 90’s, passing around cassettes or CD singles, hearing SLTS on the alternative radio circuits, perhaps watching the music video on MTV. Kurt Cobain, clad in that oversized sweater frying out his voice on mumbled lyrics that are impossible to decipher clearly on the car radio. You can hear the chorus’s words just fine, but the verses are cryptic deluges of vocal fry and syllabic ambiguity. Weird Al Yankovic parodied this brilliantly in his video for “Smells Like Nirvana”, bags of marbles gargling out of his mouth. Regardless of all that, you feel the energy, the meaning, the intensity of this moment, you bear that badge with you for a lifetime. “Smells Like Teen Spirit”, doesn’t it?

21.Song:I Wanna Dance With Somebody (Who Loves Me)
Artist:Whitney Houston
Album:Whitney
The extreme digital sheen of the intro, with the Roland TR-808’s drum kit clanking with precision alongside a Moog synth bass line, can be off putting to someone noticing this song’s position on this playlist. After all, it instantly dates it to the mid-80’s, an era of popular music not exactly associated with warmth and humanity. Then Whitney Houston starts singing. In an age before auto-tune, you had to have either a really good producer or actual vocal talent. Whitney not only brings the latter, she renders the former moot. This might be the most extraordinary vocal performance in pop history. Just listen to how she modulates her voice in the beginning chorus [1:02] versus the triumphant final one [3:36]. This steady progression tells a story, not only of Whitney’s own turbulent, tragic life, but of anyone who has ever desired a connection on the dancefloor. Her joys are contained here, her greatest achievement.

20.Song:The Calvary Cross
Artist:Richard & Linda Thompson
Album:I Want To See The Bright Lights Tonight
I regard the opening :50 of this song to be among the most interesting pieces of music in all of our rich history. But exactly why remained a mystery to me for quite awhile. Certainly the contrast between it and the rest of the 3:53 runtime is pretty stark, but in order to balance out my thoughts we should explore it. Richard Thompson’s vocals are isolated in the mix, cutting through the emotional grime with a light touch of spring reverb, reciting a litany of laments “I’ll hurt you till you need me”, slowly revealing his own faults in a toxic relationship as his partner, Linda Thompson “Ooh”’s alongside him “My claw’s in you and my light’s in you/ This is your first day of sorrow”. Back to that intro, knowing all of the context that the rest of the song is giving us, the guitar playing as if personally wounded, I find clarity in its purpose; What does one receive before a cross? Absolution. “Everything you do/ you do for me”…

19.Song:Seventeen
Artist:Sharon Van Etten
Album:Remind Me Tomorrow
Wisdom is always chasing youth, when it finally catches us, are we not allowed to grieve our former naivety? “I wish I could show you how much you’ve grown”. Sharon Van Etten’s “Seventeen” is a big, dirty, epic. The synths that soar throughout are often gritty, laying themselves out much like a gravel road. Thankfully, there’s some grace here, the electronic drums, with the signature retro-80’s sound of recent times, are a steady heartbeat keeping us centered. The Springsteen-ian pianos clumsily interpose themselves onto Sharon’s nostalgic verse. “I know what you’re gonna be/ I know that you’re gonna be…/Afraid that you’ll be just like me”. Her voice distorts heavily as she sings those lines, as if she is breaking through the temporal walls of time to warn her younger self of the trials to come, of the joyous potential of maturity. “You think you know something you don’t”. It’s moving. Slowly but surely, it takes us where it needs us to go.

18.Song:Prayer In Open D
Artist:Phoebe Bridgers/ Emmylou Harris
Album:To Emmylou: A Tribute To Emmylou Harris/ Cowgirl’s Prayer
“There’s a valley of sorrow in my soul”. While Emmylou Harris’s original has a distinctive country edge to it, it failed to tap into the ancient, haunting, energies that its lyrics implied. Phoebe Bridgers’ cover is, by direct contrast, an astonishing read. With a warmly recorded acoustic guitar providing the sole backing, Bridger’s reverb drenched vocals soar with the lyrics, rather than against them. Undulating with the tides of eternity. “There’s a river of darkness in my blood/ and through every vein I feel the flood”. Still, these are Emmylou’s lyrics and they do speak to some lost horizon of human empathy, towards oneself, towards some innate spiritual need encased in every soul. With the guitar’s arpeggiated notes ringing out like bells; Phoebe Bridgers unlocks the power in her words, giving us a song that truly captures our inherent contradictions, our inner battles, the “valley of sorrow in [our] soul[s]”. A truly wondrous achievement.

17.Song:Hallowed Be Thy Name
Artist:Iron Maiden
Album:The Number Of The Beast
Iron Maiden is the greatest metal band of all time, don’t let anyone tell you otherwise. All other contenders fall by the wayside simply by the sheer volume of great work Maiden has put out over their entire career. Here is the monument to their greatness that I suspect will still be listened to in a hundred years. “Hallowed Be Thy Name” succeeds because it tells a tale almost literally as old as time, of someone facing death and reckoning with life. It has the ageless feel of old folk tunes mixed with the inevitable gallop that Maiden can always trot out. Bruce Dickinson gives his best performance “The sands of time for me/ are running looooooooooooooooooooooow”. The twin guitar assault, the stereo field filled with bombastic drums and thumping bass, it’s as majestic as it is unrelenting. Then comes the thrashing guitar solo, soaring above the slaughter like a demon rider searching for souls to capture. As influential as it is timelessly gargantuan.

16.Song:Fortunate Son
Artist:Creedence Clearwater Revival
Album:Willy And The Poor Boys
There’s a moment in the video game Bioshock Infinite, a game where violence is endemic to the structures of society, where you come across a former slave singing “Fortunate Son”. As the soundscape in the background roars with riotous crowds, constant gunfire and explosions, the defiant tone she strikes also rings tragic. So we find Creedence Clearwater Revival, amidst a decade of hopeless wars, correctly sizing up the general mood. Harnessing the trappings of southern rock, the clear guitars on one channel contrasting with the deep-fried distortion on the other, the drums rollicking along like a steam train, John Fogerty’s rough-hewn vocals resting on top of it all. It, quite simply, rocks. “And when you ask ‘em “How much should we give?”/ ooh, they only answer “More, more, more””. With such a powerful, roiling momentum to its message, I suspect that this song will forever find its muse in any age of conflict.

15.Song:Ghostin
Artist:Ariana Grande
Album:thank u, next
Opening with unnerving, pitch shifting, synth pads, here is a song that hits with the disorientating intensity of heartbreak. “I know that it breaks your heart when I cry again/ Over him” Modern day relationships are rife with mixed emotions and unspoken traumas. So, here we have Ariana Grande singing about loving someone else while in the embrace of another, who she still clearly cares for. Instead of “Ghostin’ him”, she struggles with letting go. A cynic could take this at face value, but we’ve all suffered enough to share in Grande’s faltering performance as a collective totem. The Ariana Grande Wiki claims that she couldn’t bear to record a third verse for the song, instead populating the stereo field with orchestral swells and overlapping harmonies. It’s an emotional denouement for her (and allegedly for her former partner Mac Miller), for us, for everyone with forlorn hopes and confused feelings. (1)(2)

14.Song:The Art Of Peer Pressure
Artist:Kendrick Lamar
Album:good kid, m.A.A.d city
In a lyrical universe where the social dynamics of Compton made violence and crime as inevitable as they were tragic, Kendrick’s mother wisely states “One day it’s gonna burn you out”. After a stormy intro of neo-soul and record noise, he couches the remaining seedy depictions in a warm bath of thumping kick booms and square wave synths. The dynamics shift around to match the storytelling, culminating in a frantic near-escape from the law after a robbery “We made a right, then made a left, then made a right/ Then made a left, we was just Circlin’ life”. There is a certain cinematic texture that this song successfully captures; that of the 1990’s “Urban” film, the Boys In Da Hood, Menace II Society types. One imagines that Queen Latifah and Tupac were constant sonic companions on the “Missions” that Kendrick Lamar deftly raps about here.”I’ve never been violent/ Until I’m with the homies”.

13.Song:Valerie
Artist:Mark Ronson Feat. Amy Winehouse
Album:Version
Amy Winehouse had a peculiar way of making the old masters sound completely obsolete. The way her gin-drenched vocals worked a lyric, you would swear she had had a few affairs with it. This makes the tragedy of her life all the more bittersweet when encountering “Valerie”. Here is a song that shows just how much music needed her. Taking a completely, and I do mean thoroughly, forgettable original rock song and, with the help of Producer Mark Ronson, morphing it into this glorious wall of sound, it’s a triumph of joyous humanity. [I highly suggest sticking with the version on Mark Ronson’s album and not the (‘68 version) seen on some posthumous collections. Slowing down the tempo robs her performance of its vivid effervescence.]. Amy sounds like she can live for nothing else but singing this song, in this moment, forever. Maybe that explains the opening “”Alright it’s rolling” Sorry, Charlie Murphy, I was having too much fun”.

12.Song:Like A Rolling Stone
Artist:Bob Dylan
Album:Highway 61 Revisited
“It’s Impossibly good. How can a human mind do this?”[1] Said Phil Ochs when listening to this most historic of albums for the first time. This is a line that’s been beaten to death, but if you are going to have a quote, have one as concise as this one handy. It also speaks to the very unique way that Bob Dylan’s mind worked at the time. For a song that has gained accolades everywhere, it seemed to have had very little preparation going towards its making. Dylan simply showed up with his band and ground out an epic, no rehearsals, improvising the lyrics and melodies as it took form. This ad-hoc bohemian parade allows the song to feel like a living, breathing, entity, open to flaws, dismissive of perfection “Like a rolling stone”. From the way that Dylan’s mic pans weirdly at 0:23, to that grand organ riff that propels the song forward, no other song quite captures the essence of a life lived free of pretension. Even if it is, functionally, a giant f-off.

11.Song:Both Sides Now
Artist:Joni Mitchell
Album:Clouds
This is as simple as folk gets. A girl and her guitar, wistfully singing and forlornly strumming. It would be blase if “Both Sides Now” wasn’t so life-affirming. Those strummed chords, loads of Gadd9’s, D’s and Asus4’ths really make it seem as if the subject of the song is floating through life, not without care but also without much consequence when measured against events. The lyrical pattern of a first verse setting up vivid imagery (those famous “Ice Cream castles in the air” or “Dreams and schemes and circus crowds”) collides into the brick wall of realism in the second (“But now they only block the sun” or “But now old friends are acting strange”). Joni does this three times, each flowing into the other effortlessly, each time she relents “I really don’t know __ at all”. Where other singers would lean into technique, Joni allows her voice to carry her and us along the shifting tides of fate, of love, of ice cream castles in the skies.

10.Song:Tomorrow Never Knows
Artist:The Beatles
Album:Revolver
Having arrived at the top ten, I feel we must take stock of the sheer breadth of musical textures, topics and structures we have encountered so far. From ferocious death metal to flowery acoustic folk, from soaring synth pop to intimate indie screams. It would seem that every discernable edge has been skirted, oodles of sonic textures and charismatic singers have been courted, is there a song out there that could possibly encapsulate all of the madness that came before? Nowhere have we come across a song quite like “Tomorrow Never Knows”, a colossal achievement in recording technology and composition. Critic Jim DeRogatis, in the fascinating essay book Kill Your Idols, described “Tomorrow Never Knows” as a “violent spiritual rebirth”. That’s about as apt a description as you are ever going to get about this song, but it is worth it to dive into what exactly he meant with those words.
In this hyper, manic, mixture of tape loops and droning bass guitar is a churning emotional storm. Paul McCartney’s laughs are turned into seagulls being swept through the tempest. The soaring brass sections can be a helpful marker but they too are swept up in the sonic mass. So what’s so “violent” about all of this? I think it’s the drums. This may be Ringo Starr’s most vital moment as a member of The Beatles. He plays like a man held at gunpoint. Nested on the tapes at Abbey Road are the strains of a man possessed, precision chaos centering the storm. Hi-hats and Snares pounding their way through the mess with all the clarity of thunderclaps. “Turn off your mind/ Relax and float downstream” comes off as a sick joke on the listener, how can one relax and float down this stream? One so rocked with tempests that the song threatens to topple over under the strains of its construction.
As to the “spiritual”? John Lennon did state to producer George Martin that he wanted to sound like the “Dalai Lama chanting from a hilltop”. To fulfill this not at all insane request, George turned to the studio engineer Geoff Emerick for a miracle. He hit upon passing John’s voice through a Leslie speaker. The result was the imaginative being turned into crystal clear reality. John had his “Spiritual” chants uplifting the listener. “Rebirth”. That word is the key to understanding this song. In the context of world culture and its place in history. Before “Tomorrow Never Knows”, John was writing lyrics about love. After, he was forever drawn down the path towards lines like “I Don’t believe in Beatles/ I Just believe in me” and “The dream is over”. The dream of forever love was indeed dead, John was reborn and music was never the same. The future was uncertain, for the band, for the world, it was as Ringo said “Tomorrow Never Knows”.

9.Song:Running Up That Hill (A Deal With God)
Artist:Kate Bush
Album:Hounds Of Love
“It doesn’t hurt me” What doesn’t hurt you? Is it the sacrifices you would potentially have to make for your deal with God? Or is it the pain of knowing that your partner will never be able to fully understand your position? There’s a lot of buried emotion constantly threatening to be unleashed in “Running Up That Hill”, probably the pop song that most captures the halting breaths of a well-worn romance novel. That opening synth, as constant as a chilling wind, that haunts the entire song with its presence, those Fairlight synth hits, forever flitting in and out on gusts of atonal gales, the drums, programmed by Del Palmer, propelling us along towards something approaching an emotional denouement, all of it, just providing the lush sonic bedding for Kate Bush herself to draw us in to her personal apocalypse. Her voice rises above, every chaotic whisper and rising ooh bobbing us along on her passionate tides.
“And if I only could/ I’d make a deal with God” She cries out, the synths sounding like glass shattering around her, the pieces slowly falling to the ground. “And I’d get him to swap our places” Her voice really does sound on the verge of an emotional breakdown, her captivating soprano soaring through the chaos. “Be running up that road/ Be running up that hill/ Be running up that buildin’”. You get the sense that she would, in fact, do anything to alleviate the constant mindgames of a troubled romance, you also get the feeling that maybe it’s too late for band-aid fixes or Hail Mary’s. With the music swirling in the C minor key, a foreboding sense of sadness can’t help but permeate the speakers, but in such a way that haunts popular music to this day. Any pop song that attempts to have a driving melancholic beat with moody accompanying synths owes more than a little debt to Kate Bush here (ie: Taylor Swift’s “Style”).
But as I wrote before, there is a sense that even a deal with God would do little to mend things. “Is there so much hate for the ones we love?” her voices crumple in on her, cramming her lead vocal into the center while two vocals take over each speaker, before “Oh, Tell me we both matter, don’t we?” has her singing alone, in a pleading tone. It’s too late, maybe the partner said on the way out “Frankly, my dear, I don’t give a damn!”. Maybe this is why we have Kate Bush’s vocals freaking out near the end, a seemingly endless cacophonic wail of voices, none making sense, all clearly in distress. The swapping of places begged for in the chorus takes on a chilling air after hearing all of that. Why would you wish such emotional hell on anyone and expect good things to come of it? Alas, you have Kate singing in lower registers at the very end, as if she is going to stoop to making a deal with a different sort of God. One that can make that deal.

8.Song:Hurt
Artist:Johnny Cash/ Nine Inch Nails
Album:American IV:The Man Comes Around/ The Downward Spiral
It’s crazy how much a tiny change to a lyrics sheet can affect so much of a song’s meaning. By re-writing “This crown of shit” to “This crown of thorns” a monumental shift has occurred. From Trent Reznor’s blistering, fecal, original, Johnny Cash turned a drug-addicts worst nightmare into an old man’s final regrets. As the full scope of his life is laid out before him. Little wonder that Trent famously exclaimed that “that song isn’t mine anymore” [1]. How could anyone walk away from hearing this song, watching that music video, and not feel as if they had wrangled with a lifetime of guilt? It just goes to show how important interpretation is when poring over a song’s potential. One tiny alteration changing the world of the song entire. Instead of allowing us to wallow in our own filth, this version fills the listener with a spiritual uplift, beckoning them to reflect on their lives while the time is there.
Back to that music video, the gall of seeing Johnny Cash, his face worn ragged by age, as he pours wine over his feast, playing his guitar as if he can barely hold down the strings as his mouth barely opens. June Cash hovering behind him, in full knowledge of their own mortality, trying desperately to wring some meaning out of a life long lived. The artefacts of Johnny’s musical career giving him little meaning at the end. The terrifying reality of mortality interfacing with the ravages of the mind as a result of aging, “You are someone else/ I am still right here”. There are moments in the chorus, where images of a younger Johnny flash across the screen, where we can’t help but be carried along on the empathetic torrent “What have I become, my sweetest friend?”. Capping things off with one of the other horrifying aspects of time passing on “Everyone I know/ Goes away in the end”.
But Johnny Cash is allowed to keep his dignity, to spark one final glance at the roads he travelled, thanks to the production. Listen to how Rick Rubin surrounds Johnny with an acoustic guitar that sounds as worn as his faltering vocals, with pianos that ring out with precision and clarity. Listen again to how Cash’s voice peaks the microphone in the chorus, more so in the final one. As if the cascade of supercut memories is overwhelming the senses “And you could have it all/ My empire of dirt”. But Cash will have the final word on his own life, no matter what has happened, all the trials and tribulations, no matter what regrets he has nursed all of these years, “I would keep myself/ I would find a way”. If great art is the bringing together of all that we care to remember and turning it into something we hope no one will forget, then “Hurt” is a monument to our drive for shared understanding and determination.
Stay tuned for Part 22: 7-1 And Afterword
If you would like to listen along, here is a link to the Apple Music playlist and the Spotify Playlist.
Index Part 1: Foreword, Part 2: 500-476, Part 3: 475-451, Part 4: 450-426, Part 5: 425-401, Part 6: 400-376, Part 7: 375-351, Part 8: 350-326, Part 9: 325-301, Part 10: 300-276, Part 11: 275-251, Part 12: 250-226, Part 13: 225-201, Part 14: 200-176, Part 15: 175-151, Part 16: 150-126, Part 17: 125-101, Part 18: 100-76, Part 19: 75-51, Part 20: 50-26, Part 21: 25-8, Part 22: 7-1 And Afterword

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