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06.28.14 Exile In Guyville: Ranked06.27.14 Darkness On The Edge Of Town: Ranked
06.26.14 Dummy: Ranked06.25.14 The Devil And God Are Raging Inside Me:
06.24.14 Maxinquaye: Ranked06.23.14 10 Least Awesome Elliott Smith Songs
06.22.14 Transatlanticism: Ranked06.21.14 Mezzanine: Ranked
06.20.14 Yankee Hotel Foxtrot - Ranked06.19.14 Top 20 Elliott Smith Lyric Quotes
06.18.14 "you Forgot It In People" - Ranked06.17.14 "pure Heroine" - Ranked
06.16.14 Album Track Rankings: Loveless06.05.14 My Top 50 Songs (with Explanations)
07.21.13 Top 20 John Mayer Songs05.31.13 Top 5 Jeff Buckley Songs (not On Grace
05.31.13 Top 20 Radiohead Songs05.30.13 Top 5 Closing Tracks
More »

My Top 50 Songs (with Explanations)

My Top 50 Songs at the moment. I imposed a 3 song per artist limit. Hope you all enjoy!
1Jeff Buckley

How do I even begin this review? How can I to try and summarize my feelings for this seven minute pop song in a way that doesn't come out as some sort of incomprehensible novel? I guess I'll start with this: In the center of the world's greatest album, the world's greatest singer interprets a Leonard Cohen song and crafts the world's greatest recorded song.
I'm sure most of you have heard this song at some point in some variation, though not necessarily this particular cover, (many people think of the John Cale cover that appears in "Shrek", or of the Rufus Wainwright cover, which are two completely different animals.) You've no doubt heard it sung on American Idol or some other singing competition show by some aspiring pop star. There's even a solid chance you've heard it soundtracking a TV series, or even playing on the radio or in the mall on a rare occasion. The bare bones of the song are ubiquitous in one way or another. Yet this definitive cover remains untarnished by exposure and lesser variations, which is a testament to its greatness. Jeff Buckley's "Hallelujah" isn't so much a pop song as it is a spiritual odyssey that flows through the listener and keeps them suspended in its divine thrall. My best friend once remarked that she preferred the Rufus Wainwright version to this cover, and I can see her perspective. Comparing this to other cover versions is folly. Most of them concentrate on the melody and make the song as compact as possible, turning it into a very good pop song. Lately there has been a tendency to to turn the song into an orchestral, holy event with grand production. By contrast, this one is drawn out and bare bones, using only an acoustic guitar and Buckley's voice, both of which are divine. So it's certainly not as catchy or easy to sing along with as other versions. But as a piece of involving art that touches the soul of anyone who hears it, this cover blows everything else out of the water.
The lyrics that Leonard Cohen wrote have been endlessly analyzed and debated. Many people automatically assume that "Hallelujah" is some sort of holy prayer, and in fact feels like a hymn in its approach no matter who is singing it, but lyrically it's not exactly the kind of thing you say with hands clasped together at your bedside at night. References of sexuality abound, and the song is more elegiac than it is reverent. Buckley famously stated that his version was a "Hallelujah to the orgasm", after all. I would offer my interpretation of what the song "means", but honestly it would inevitably be different than your own, and even my own interpretation is liable to change based on the context of my hearing it. It's simply an amorphous, ever-shifting passage.
However, Buckley understood that definition isn't as important as experience. You may not know exactly what "Hallelujah" is trying to say, but you can feel its wispy cool embrace swirling around you. Buckley had a versatile voice and was completely capable of effortlessly power-housing any song that he felt like dominating, (check out his singing at the end of "Grace" and you'll experience something akin to an exorcism), but here he gives an understated, angelic reading that fills the song with subtle nuances and shifts. And it is through Buckley's soulful voice that we understand what "Hallelujah" does so successfully, and that is mapping out the highs and lows of the human experience. Buckley's voice can convey so much within the span of a few seconds. One moment evokes the surreal bliss of undressing with someone indescribably beautiful for the first time; and the release of inhibition provided by that first kiss as you embrace them next to the bedroom window clouded by the drizzling night rain. Yet simultaneously, you can feel the dejected sigh of innocence as it withers away when those lips connect, and then the sorrow brooding from the aftermath of what was once lust, now long since faded into numbness. While there is some lyrical support that helps craft this feeling, it is Buckley's voice that provides the depth and texture that gives each listen a slightly new experience.
Ultimately though, I'll never truly be able to tell you why this song is the greatest ever made. There is no way for me to describe it in a way that would sufficiently echo your own experiences. But allow yourself to sink into this song, and it is bound to move you something holy.

The greatest song U2 ever wrote is the one that supposedly saved them from splintering apart and allowed them to create the fantastic "Achtung Baby". Almost universally agreed upon as one of the finest rock songs ever made, "One" not only paints a picture of a failing relationship, but also symbolizes a message for the world as a whole. It's highly ironic that "One" is played at so many weddings, as anyone listening with intent ears will notice just how bitter it is. Lines like, "Did I disappoint you/or leave a bad taste in your mouth?/You act like you've never had love/and you want me to go without", and "Have you come here for forgiveness/Have you come to raise the dead/Have you come here to play Jesus/to the lepers in your head" don't exactly sound like something you'd hear walking down the aisle. But as bitter as the song is, it's possibly the most uplifting song ever made. "One" is a song that acknowledges the conflicts and differences between people, whether between lovers or the population at large, but it recognizes that it is only through coming to terms with one another that we will persevere. It is not an easy concept to swallow, but after three and a half minutes of pain and struggle we are given nothing less than the greatest minute in music: An inspirational guitar solo so powerful it's as if beams of pure light are erupting from the surface of the Earth. As great as the studio version is, there's a live version of the song that is played during their Vertigo tour that I feel is even more passionate and powerful, and extends the duration of that magnificent closer. Fittingly enough, "One" was my number one song for a long time until it was eventually usurped by this upcoming selection, and it continues to send shivers down the spine regardless of how many times I've listened to it.
3Massive Attack

I first came across this song in the same way I'm sure a lot of people did: The opening title sequence of "House M.D." That opening rhythm that was so reminiscent of a heartbeat mixed with that hypnotic harpsichord pedal was powerful and addictive in its own right. Just the instruments alone make you feel like you're deeply submerged in a pool during a rainstorm at dusk, and you open your eyes underwater and see the rain dance across the surface above your head. Little did I know that this was just a sample of a phenomenal song, and that I hadn't even heard the best part. The entirety of "Mezzanine" is the abyss; pitch black and alien; and "Teardrop" swims in that dark emptiness. And then, a ray of light shines through; calling out like an ethereal spirit to the listener stuck in the void. That ray of light is Elizabeth Fraser, with a voice so gorgeous and pure that it seems not of this world. Her performance here is one of the great vocal contributions in popular music, imbuing this track with a soul; albeit a cryptic and alien one. I vividly remember hearing this track for the first time; I don't believe I've ever been so overwhelmed and in awe of any piece of music upon the first listen in my life, (including "A Day in the Life".) I was immediately enraptured by it, and since then have searched high and low for something that could rival this song's impact. Years of fantastic musical discoveries have followed, but very little has quite matched up to the majesty of the song that set me on the path to begin with.
4Elliott Smith
Waltz #2 (XO)

If you only listen to one song from this whole list, make it this one. It's not that I don't know people who are impartial to this, because I do. But it's a song that can register with anyone, even people I would never expect it to register with. One of my close friends is a fan of metal and Japanese pop music, and feels like most music needs to have an extremely fast tempo to keep her attention, (to the point that "The Downward Spiral"-era Nine Inch Nails was considered "boring" to her.) I showed her this song, and she later declared it was one of her top three songs of all time. I showed this to another friend in her car, and while she is pretty open to most musical styles, she generally listens to the radio as much as anything. She later told me that she looped the song during her entire hour-long trip back home that same day. Even my dad, a country music fan who generally doesn't get into the vast majority of my music, can be heard humming along to this thing when I play it. This song has a universal appeal no matter which way you slice it; whether you're a casual music listener or a compulsive one. So what is it that makes this the crowning jewel of Elliott Smith's stacked catalog? Well for one thing it's got an incredible melody and and incredible lyrics, but you could say the same about almost every song he ever made. Perhaps it's because "Waltz #2 (XO)" is the perfect blend of the intimacy he showed on his earlier records with the production levels of his later material. Or maybe there's just something magical in this song's essence, and we should just shut up and replay it again for the millionth time, because a song this flawless will never get old.
Fake Plastic Trees

The biggest surprise on the list for me is the lack of Radiohead. They are a top five act for me, and if this were a Top 200 list instead of a Top 50, they'd be swarming all over it with diverse selections like "Paranoid Android", "Pyramid Song", "Reckoner", "Jigsaw Falling Into Place", "Idioteque", "Everything in its Right Place", "How to Disappear Completely", "Street Spirit (Fade Out)", and "Airbag". Yet at the same time, they fall into the same camp as Arcade Fire and Stevie Wonder: Lots of incredible material, but with few definitive songs. To me, their best song is still this gem from their sophomore album, an affecting ballad of disillusionment and depression. Yorke's voice is still beautiful here, before he grew to hate it and started glitching it up, and here it soars over the atmospheric instrumentation. There's not much to say here except that "Fake Plastic Trees" is a song that truly possesses you; flows through your entire body like a spirit that exhales out of your belated breath. It's the sound of feeling like a ghost in your day to day life and wanting nothing more to break out into the land of the living; to feel something, anything; to "blow through the ceiling..." Radiohead went on to create better, more varied, and more interesting albums than "The Bends", but they never again made a song that was quite as perfect as this.
6Jeff Buckley
Forget Her

The hit single that never was? At least that's what the record executives were planning. The issue was, this song was far too personal for Buckley; too painful for him to sing. So it wasn't released until after his death, replaced by "So Real" on "Grace" at the last minute. He simply couldn't let this be the song that he became known for, as doing so would be too torturous for him to bear, (which is saying a lot from someone who had already recorded a slew of all-time great breakup songs on the same album.) But in fairness, had it been left on there, there's a good chance it could have been his breakout single. Other songs have taken Buckley's voice to the limit in various ways, but he never sounded this much in pain on anything else. The song has a pretty simple structure, and is about a former lover that hurt him deeply, and whom he now loves and hates in equal measure. Now all that he wants to do is get over her; get her out of his head, but he despairs that this is impossible. This isn't the bittersweet farewell of "Last Goodbye"; this is the sort of jarring separation that causes former lovers to reach for the bottle or some other way to numb the pain. When Buckley comes lashing back after the instrumental passage in the center with, "My tears are falling down as a I try to forget/her love was a joke since the day that we met/All of the words/all of the men/all of my pain when I think back to when", it becomes clear that this might be the most harrowing song about heartbreak ever recorded.
Where the Streets Have No Name

We follow up my #1 album closer with my #1 album opener; the first track of "The Joshua Tree". I've made prior reference to this being an incredibly cinematic album, and this song does a perfect job of establishing the scope of the ten tracks that follow. The first minute of the song is wordless; starting with a shrouding organ mist establishing a blank desert scene, and then we hear...running. Someone running through the desert; propelled by those chiming guitars. Running to who knows where, but we know they have some sort of mission. And then, the lyrics come in: "I want to run/I want to hide". The lyrics in this song are incredibly solid, but more importantly, they are sung with enough passion to fill an entire stadium. When Bono sings "We're still building and burning down love", we feel a wave of pure energy washing over from a single cymbal crash that echos the fiery soul of its album. I've heard criticism of U2 taking themselves too seriously, but if music this enormous and spine-tingling is the result, then I couldn't care less. And the closer, which refrains the opening guitar chiming while using shock-waves of rumbling bass blasting throughout, leaves the listener speechless; feeling like nothing the band will do can top such a spectacularly earth-shattering and soul-soaring intro. They would be both right and wrong: One of the greatest rock albums ever made would soon follow, but no song therein would quite match the peak of that stellar opening.
Glory Box

Earlier I praised "Roads" as Beth Gibbon's most pure and fragile vocal performance. That may be true, but this is unquestionably her sultriest. In fact, this song in general is one of the coolest, sexiest tunes to ever come about; yet that doesn't take away from how epic and addictive it is. Probably the greatest album closer I've heard, (including "A Day in the Life"), "Glory Box" is the culmination and release of everything on "Dummy": The cigarette smoke at a jazzy bar floating over spilled whiskey; a cool sense of classiness that even James Bond would aspire to. After ten tracks of Beth Gibbon's haunted past and festering pain; after ten songs of deep blue necessary catharsis, "Glory Box" is the awakening of a new Gibbons; no longer held back by the chains of the past that kept her emotionally locked down. The deep blue has been replaced by violet with shades of scarlet as Gibbons ferociously sings out, "Give me a reason to love you/give me a reason to be/a woman." Adrian Utley's guitar shredding definitely helps turn things up a notch in a way that simply didn't exist on the other (still stellar) tracks on the album, but make no mistake: Beth Gibbons is always the star of whatever song she's in. Portishead has made a lot of incredible songs, but while not the most indicative of their overall sound, "Glory Box" remains their most perfect creation.
9John Mayer
Covered in Rain

Having Mayer this high up on the list is bound to surprise some people. It really shouldn't. As a studio artist, Mayer is solid, (far more so than most any pop act on the radio today), and has flashes of great material under his belt. But when he's live, he goes into an entire different stratosphere, (anyone who has listened to his "Where the Light Is" double live album can testify to that.) He's also an exceptionally talented guitarist, and in that regard this early-career live recording is his finest hour. At one level it can be interpreted as just another breakup song, but like "Jesus Etc", there is a post-9/11 context that gives it an atmosphere of trepidation and uncertainty. It's even possible that this complicated environment is what numbs this couple to the point where they eventually fade away from one another. There's a prevalent sadness lurking within the characters in "Covered in Rain", yet the song is as comforting as it is gloomy. It's the sound of people trying to make sense of a scary and convoluted world, and in turn resorting to each other for moments of solace to keep them going; to give their lives a meaning through gentle hugs and holding hands. There is some good lyrical work on display here, but Mayer's guitar works most of the magic, and that's before the song hits the 2:45 mark, where Mayer breaks out into what can only be described as one of the greatest guitar solos I've ever heard. It's extensive without being indulgent; providing the transcendental majesty that the guitar solo is known for while also maintaining the complicated mood of the song it lives inside of. A little over a minute into the solo, there exists a moment that I can only describe as literally breathtaking; as in it forces the very air out of your lungs. I expect some criticism for choosing this song over classics like "A Day in the Life" and "Gimme Shelter", but I suggest listening to it before shooting it down as just another pop song. You might find that these songs are far closer in quality than you expected.
10My Bloody Valentine

One indicator that a song is great is if it summons up incredible emotions in the listener, yet they're very difficult for them to articulate or describe. Sometimes it's easier to describe in terms of images to come into the head rather than using terms like "happy" or "sad", (a method I've used to describe songs like "After the Flood".) Anyway, "Loveless" is an entire album that is like that: Shamelessly romantic and dreamy, yet not devoid of pain. "Sometimes" is the most personal track on the album to me, and it always leave an impact, even though it's never quite the same each time. When I hear this song, I sometimes think of its brilliant soundtracking use in Sofia Coppola's "Lost in Translation", (one of my all-time favorite films), when Charlotte and Bob are heading back to the hotel after hanging out together for the first time. Since then, it's been used to soundtrack the moment of anything poignant and bittersweet in my life: The sound of a beautiful, fleeting moment that happened in your life and lingers in your memory; one that you were sad to let go of, but you feel blessed to have experienced at all. "Sometimes" is the plane trip back from your week long vacation; it's the feeling five minutes after sharing the farewell kiss of someone you may never see again, but you know you'll never forget.
I Am Trying to Break Your Heart

I've already skimmed over how great "Yankee Hotel Foxtrot" is when I reviewed "Jesus, Etc" earlier, but as phenomenal a song as that is, this one is the crown jewel of the album. This opening track is nothing short of epic, as Jeff Tweedy lays down a bed of masterful lyrics detailing the tale of a man who has screwed up his relationship, (here via alcoholism), and is recalling everything that went wrong. It starts with him being clearly drunk and hurting his girlfriend in some way. He then tries to go back to her and apologize for his actions, but he is still under the influence of the bottle. Shortly after they've made up, the girl realizes that he is drunk once again and, unable to stand it any longer, sends him on his way. He recalls everything that has happened, realizing how foolish he has been right before the world begins to blur for him again. The song builds and builds over it's almost seven minute length, finally culminating in a noisy and powerful climax that paints a desolate picture of this character's consequences; left alone on an abandoned street with nothing but an empty beer bottle in his hand. The song shows subtle signs of psychedelia throughout; whether via those radio-style sounds in the beginning, that screech at the end, or the number of touches in between. It's both through this and it's weighty climax that it bears a certain resemblance to "A Day in the Life". The lyrics are outstanding; look no further than the opening: "I'm an American aquarium drinker/I assassin down the avenue/I'm hiding out in the big city blinkin'/what was I thinking when I let go of you." All things considered, it's a masterpiece of a song that opens up a masterpiece of an album.
12Jeff Buckley
Last Goodbye

Ladies and gentlemen, allow me to introduce Jeff Buckley; the greatest vocalist of the past century, and my personal favorite artist. The man recorded only one studio album before accidentally drowning at the age of 30, (though he also had recorded a live EP and left some posthumous material around to be unearthed.) Fortunately, that album was "Grace"; the greatest album I've ever heard. There should be no surprise that this won't be the only song by Buckley to appear on this list. Yet as staggering as it is that someone with so little existing material could have multiple songs of all-time greatness quality, it's even more shocking that there was so much more of his material that could be present here had I not established a three-song per artist limitation. Tracks like the hypnotic "Dream Brother", sensual "Everybody Here Wants You", tearful "Lover You Should've Come Over", and the bittersweet "All Flowers in Time Bend Towards the Sun" all could have very well made it into the top 50. And that's not even counting great songs like "Mojo Pin" or "So Real".
As it stands though, "Last Goodbye" wins out in this spot in a cat fight. It was his most successful song during his lifetime, and is one of his best. A fully realized breakup song, the bittersweet "Last Goodbye" maturely and perfectly relates to the pain of letting go of someone you love even though you know it's simply not meant to be. The play by the band is stellar and the production strings give the song an extra level of beauty. Yet as always, it's the voice of Buckley that makes this song what it is. The lyrics are very strong on their own, but no one could get more out of a lyric than Buckley could. "This is our last goodbye/I hate to see the love between us die/but it's over/so just take this and then I'll go/you gave me more to live for/more than you'll ever know" is a good opening stanza, but Buckley's voice opens us up to every fond sepia-toned memory and aching bruise of that relationship; adding endless layers to the song and conjuring more tears from the eyes than the lyrics themselves could ever do alone. This sort of thing was his gift, and thank God he was able to give some of it to the world before he died.
13Elliott Smith
Say Yes

The greatest song on Elliott's greatest album is the closing track, by the skin of its nose. The brevity of this song, (2:18 long), stands in strong contrast to the slew of nine-plus minute epics that have recently been written about here. Then again, no song I've ever heard has done so much so perfectly in so little time. Like most Elliott songs, it's infinitely re-playable, lyrically perfect, and touches you to the core. The melody is also one of his most infectious, and relatively optimistic by his standards. It's subject matter is nothing all that new; it's about wanting a true, loving relationship with someone who genuinely cares about you instead of a slew of one night stands that cause nothing but immediate regret. But it's that gorgeous melody and Elliott's hushed voice that make you cry tears of sadness while simultaneously appreciating the morning rays of sunlight pouring from your window. The emotion behind phrases like "Situations get fucked up/turned around sooner or later" is something just has to be heard, rather than written about. Go ahead and listen for yourself; it'll only take you a couple of minutes.
14Talk Talk
After the Flood

This is the best song out there that could be described as "apocalyptic", and that's saying a lot on an album that already has one of the all-time great apocalyptic songs in "Ascension Day". The difference is in the approach; most songs that are described as apocalyptic seem to emphasize the explosiveness of the event itself; bombs dropping or armies marching into battle. The closest cousin of "After the Flood" is probably Radiohead's "Idioteque", in how it observes a casual witness's perspective of the world being torn asunder while it's happening, and taking in the wreckage of the aftermath. I said earlier that "New Grass" was the dove with an olive branch in the Noah's Ark story. By contrast, "After the Flood" is the moment where you're standing on the ark and watching the sea around you consuming everything you once knew, and knowing that there's nothing you can do to stop it. It's a beautiful yet harrowing song that creates an out of body experience, showing how insignificant and hopeless as ghosts we really are in certain aspects when it comes to the grand scheme of life.
15Bruce Springsteen

The closing track of "Born to Run" is the very definition of "sprawling"; a sweeping, romanticized portrait of an urban neighborhood that could have been taken right out of "West Side Story". Springsteen shows all of these people in day and night, in their romance, their bustle, and their tragedy. It's the essence of its album boiled down into a single, epic song. And boy is it epic; over nine minutes in length; it has no less than four sections and utilizes everything a Clarence Clemons saxophone solo to the piano progression of "Tiny Dancer" (but to even greater effect.) When music is described as "cinematic", this song is one that will always come to mind.
16Brand New

Most great music, even great songs, require a lot of listening to blossom into their full potential. Sometimes, though, a song comes out of nowhere and just floors you. Such is the case with "Jesus", probably the most honest and heartbreaking crisis of faith I've heard put into song. Despite its title, the song gives no definitive stance on religion. Instead, what we get is a man at his most lonely and vulnerable, struggling with his demons, and at odds with what to believe in. Despite admitting to being a sinful person and feeling unconvinced in a higher power, he is nonetheless afraid of what will happen after he has passed away. If God does exist, will whatever remnants of broken faith he has left be strong enough to save him, and if so, will he truly feel like he has deserved such a salvation? "Jesus" is a broken man's conversation with the titular character; not so much a prayer as it is a confession to this higher power who may or may not exist in the eyes of the singer, but who is the only one left who has a chance of understanding and listening to him. The desperate cry of, "So do you think that we could work out a sign/So I'll know it's you and that it's over so I wont even try?" after a long buildup of questions and internal struggle is absolutely gut wrenching and never fails to send a shiver down the spine; a plea from someone who is so lost and scared that they want nothing more than to just give up.
17Kendrick Lamar
Sing About Me, I'm Dying of Thirst

It's impossible to delve into why this song is so great without first delving into the concept of its album. "Good kid, m.A.A.d. city" is a coming of age story set in the streets of Compton, wherein a teenage Lamar is magnetically drawn into the gang lifestyle despite his best attempts at a straight and narrow life, and its only when he sees the death of his friend and witnesses the consequences of this lifestyle does he escape from the streets. "Sing About Me, I'm Dying of Thirst" is the moment where Lamar ruminates over his mortality, faith, and the people around him; finally making the conscious decision to escape the gang lifestyle.
The song consists of two sections. The first details three letters from different perspectives: The brother of Lamar's friend that was shot, the sister of a murdered prostitute that Lamar wrote about on an earlier album, and Lamar's response to both. The lyricism in this half of the song is some of the most powerful I've heard not only in hip hop, but in music in general. Each of the letters describes different reasons for why the ghetto is such a soul crushing and inescapable place, with each character knowing that any day could be their last in such an environment, (whether they want to admit it or not.) It's so dreadful that Lamar has been looking at his life from a new perspective, and questions his purpose on Earth and what will become of him if he becomes another casual victim of the ghetto. "Sometimes I look in the mirror and ask myself/am I really scared away of passing away/If it's today I hope I hear a/cry out from heaven so loud it could water down a demon/with the holy ghost 'til it drown in the blood of Jesus" is as powerful a prayer for transcendence as I've ever heard. Midway through the song, Lamar comes to the realization that his purpose in life is to tell the stories of those urban victims so that others might avoid the same fate, and only hopes that his life will matter and that he will leave an impact on others when his time comes.
And then, the second section comes in, which is about Lamar seeking out faith and salvation; hoping that he can be forgiven for all of the sins he has already committed. While the first half is driven primarily by the lyrics, the second half is driven by looping backdrop of a gorgeous, airy voice singing wordlessly as if solemnly offering their entire being over to some divine entity as their last chance for hope. The section concludes with another powerful lyric, ("You're dying of thirst/dying of thirst/so hop in that water/and pray that it works"), before the song finally concludes with a minute long dialogue of the speaker getting saved by Christ and starting his life anew. At times harrowing, heartbreaking, and transcendent, this massive song is the most deeply moving rap song I've ever heard, and that includes "Runaway".
18Kanye West

If there's anything people know about Kanye, it's that he is an egoistical douchebag. Fortunately, he's self aware enough to know this himself, even if he doesn't do his utmost to mend his image. The brilliant "My Beautiful Dark Twisted Fantasy" is a fascinating portrait of Kanye in all of his faces, exposing how he and the public view him as artist, celebrity, hero, pariah, god, and mortal. It's a very dichotomous album, but even at its most fantastical, its always perceptive and brutally honest. Nowhere is this more apparent than in "Runaway", the heart and soul of the album, where Kanye admits to just how much of an asshole he is to the one he loves. Yet where many artists would take this as an opportunity to say "I know I'm a jerk, but please give me another chance", Kanye is too perceptive to believe that he'll change. He knows that soon this moment of searing clarity will subside and he will once again give into his vices, and whoever he cares about will suffer as a result. The best advice he can give is to run away from him as fast as they can before they get hurt. Structured upon the lonely pounding of singular sustained notes on a piano, the song's lyrics are at once sad, self-mocking, dark, abusive, pleading, and nothing less than honest. Yet the best part of the song might be the final three minutes, where Kanye's self skewering words are replaced by his voice droning through a vocoder until his speech is indecipherable. It's as if his bleeding soul is calling out from the dark isolation that he has inflicted upon himself, but its attempt at communication is muffled out from drowning in its own tears; this assuming that there was anyone left to listen at all. Kanye's most vulnerable moment, but undeniably his best.
19Elliott Smith

Elliott Smith, before his tragic alleged suicide at the age of 34, was one of the most gifted songwriters and artists of the past century. He is also my second favorite artist next to one other person who will appear on this list in due time. Elliott had a knack for combining beautiful, interesting melodies with dark lyrical content, and his consistency was matched by no one, including Radiohead. Virtually every song he made, including his incomplete posthumous releases, was very good to great in quality. Many of his songs could have made this list, and this won't be the last appearance he will make, but "Angeles" is about as good a song as any. It starts with a single sustained organ note before letting in a beautiful, intricate, haunting acoustic guitar melody. Soon Elliott's fragile voice comes in, detailing LA as a land of of broken dreams and parasites. It's a subject that's been covered many times, but the lyrics here are so strong, ("Someone's always coming 'round here trailing some new kill/Says I've seen your picture on a hundred dollar bill"), and Elliott's hushed, breathy singing so moving that this song becomes both infinitely replayable, as well as utterly soul-touching. Just like nearly every song he ever made.
20The Beatles
A Day in the Life

The first time that I ever heard "A Day in the Life" was undoubtedly one of the most memorable listening experiences I've ever had. As melodic as any Beatles song, yet with a disturbing edge that eventually turns it into something terrifying, it's as epic and powerful as five minute songs get. I can only imagine what people must have thought when listening to it back in 1967. This gets ranked as one of the greatest songs of all time routinely for a reason.
Jesus, Etc

Listening now, it's hard to believe that "Yankee Hotel Foxtrot" was recorded pre-9/11, in part because of its haunting cover eerily reminiscent of the towers, but also because of how well it tapped into the psyche of people living in a post-9/11 climate. Song titles like "Ashes of American Flags" and lyrics like "tall buildings shake/voices escape singing sad sad song" make this even more eery. "Jesus, Etc" is a virtually perfect song that on one level is simply a comforting, yet sighing declaration of love and support to someone close to the singer, ("I'll be around/you were right about the stars/each one is a setting sun" is a particularly touching lyric.) Yet with the aforementioned imagery of shaking buildings and voices crying out, it also served as a comfort to a nation trying to make sense of a disaster that would change their sense of security forever. One of the highlights on one of the greatest albums ever made.
22Brand New

Based on the real life story of a seven year old flower girl who was decapitated at the hands of a drunk driver that crashed into her vehicle, this dark song taps into multiple perspectives of those affected by the accident. It starts with the mother's elegiac, comforting, and brave-faced farewell to her soon to be deceased daughter; then it moves to the drunk driver's perspective as he tries to deal with the overwhelming guilt of the manslaughter he has committed. "And in the choir/I saw our sad messiah/He was bored and tired of my laments/said I died for you one time/but never again" are bleak lyrics indicative of a consuming guilt so strong that he feels like even Christ himself has turned his back on him for what he's done. From there, the song slowly goes from somber quietness to an escalating frenzy of madness, guilt, anger, shame, and sadness; becoming an overwhelming cacophony of voices and sounds swirling around maddeningly in the head before exploding into a screaming guitar solo that unleashes all of the bottled up grief of the preceding six minutes into tearful, cathartic rage; lashing out until there's nothing left. An unshakeable song of harrowing power.
23Frank Ocean

Two years ago, this staggeringly ambitious epic came out and showed the capability and scope of modern R&B. One half shimmering, regal dance hall throw-down and one half slow burning, sensually charged portrait of modern emotional disconnect, this ten minute track would make Ocean's artistic idols Prince and Stevie Wonder proud. It continues to get funkier, sexier, sadder, and more somber with each listen.
24Talk Talk
New Grass

"Laughing Stock" was the final album of this new wave band turned avante-garde, jazzy post rock artists. The album can be interpreted in numerous ways, but its biblical imagery, (in mythos, not in message), can be seen conceptually as the remnants of humanity witnessing the apocalypse. "New Grass", the penultimate track on "Talk Talk", is the sound of hope and rebirth after a cataclysmic disaster, and is the album's most purely beautiful track. This song is the dove carrying an olive branch in the story of Noah's Ark; a sign of hope, peace, and light in an obliterated world. There is a lingering sadness that comes with the extermination of life as we know it, yet it's illuminated by the cautious optimism and excitement that comes from starting anew.
25Yeah Yeah Yeahs

"Maps", or "My Angus Please Stay", stands in strong contrast to the moaning and wailing that Karen O spits out during the preceding tracks of "Fever to Tell". Here she drops the attitude and gives a vocal performance full of longing, backed by a tune both catchy and heartfelt enough to make this the defining indie love song of its generation.
26Bruce Springsteen
Thunder Road

The opener to Springsteen's romantic breakthrough album is a lyrical goldmine and the anthem to anyone who has wanted to break out of their current position and experience something adventurous and new. The storytelling here is so perfect that it's impossible to pick out a choice lyric; once I start quoting this thing, I won't be able to stop.
27Arcade Fire
Sprawl II (Mountains Beyond Mountains)

Arcade Fire is sort of like Stevie Wonder, in the regard that they have a wealth of great songs to choose from, but it's hard to pick out a definitive single to represent them. While "Neighborhood #1 (Tunnels)" and "Rebellion (Lies)" are far more representative of their style, their best song is the penultimate track of the cinematic "The Suburbs"; those luminous synths and R?gine Chassagne's soaring voice creating the perfect climax to the hour long journey leading up to it.
Purple Rain

If only all power ballads were this good. One of recent history's most wildly creative artists lays down this opus at the end of the album of the same name; a dominant display of guitar prowess, emotional directness, and hazy atmospherics.
Smells Like Teen Spirit

Yes, it's almost certainly the most influential song of the past twenty five years. Yes, it wiped hair metal off the map and opened up a portal for all sorts of alternative artists to flourish and yadda yadda yadda. The reason it makes the list is because, even after two decades of overexposure and discussion, it's still melodic, cool, and unmistakably rocks. The go-to anthem of Generation X still holds its power well into the 21st century.
30Bon Iver
Skinny Love

After the dissolution of both his band and his relationship, Justin Vernon caught a case of mono and hibernated in the Wisconsin woods for three months to record a folk album. "For Emma, Forever Ago" is loaded with ace material, but this is the crown jewel of the lot; an otherwise straightforward song overflowing with long festering sadness, anger; and most of all; pain.
31Stevie Wonder
Living for the City

Stevie was an ridiculously talented man that created an endless amount of classic music, but this ambitious and vibrant song about race relations stands as his magnum opus. It's also perhaps one of his strongest lyrically, with lines like "To walk to school/she's got to get up early/Her clothes are old/but never are they dirty" painting an in depth portrait of holding one's dignity in the midst of a suffocating urban struggle.
32The Cure
Pictures of You

A seven minute Gothic masterpiece that doesn't waste a second of its run time. Sparkling and recklessly sincere; brimming with shameless displays of emotional pain evaporating into catharsis incarnate. Will have you wanting to stand out in the pouring rain with arms raised high, "Shawshank Redemption" style, screaming the lyrics while the gorgeous music swells from all around you.
33Van Morrison
Into the Mystic

This song is simply magical. If you're looking for a piece of bottled nostalgia to take you back to the last loving breaths of the 60s, look no further. That's not to imply that this song is dated, but simply that a song this gloriously spiritual, carefree, and well, MYSTICAL, couldn't possibly exist in any time period other than one that we so heavily romanticize; this assuming that it exists within our time at all.
34Nick Cave and the Bad Seeds
O Children

Being a huge fan of the Harry Potter books, I found it incredibly ironic that the best scene in the otherwise underwhelming "Deathly Hallows: Part 1" film wasn't even in the book. J.K. Rowling never penned a word about Harry and Hermione dancing along to the radio in a tent, but audiences everywhere responded to this display of two young adults having to grow up way too fast; trying desperately to hold on to the fading slivers of light remaining in a hopelessly bleak world. For those who were touched by that scene of cinematic brilliance, you have this song to thank.
35Massive Attack
Unfinished Sympathy

The progenitors of trip hop came right out of the gate with one of the genre's towering epics. Shara Nelson's voice, swelling strings, an incessant clicking rhythm, and more combine into something soulful, eery, beautiful, and grand.
36Modest Mouse

To me, Modest Mouse are a textbook definition of a band that is good but overrated. However, I've heard one glorious moment from their catalog that predates the likes of "Float On", "Third Planet", and "Teeth Like God's Shoeshine", and its this epic drug ballad of heartbreaking beauty. A lo-fi classic that is unapologetic-ally pretty and desolate in equal measure, this song alone nearly justifies the hype of its band.
I Still Haven't Found What I'm Looking For

One of the hit singles on one of the greatest rock albums of all time perfectly establishes the cinematic scope and tone of what was to follow. The idea of soul searching inside the American continent, through it's barren deserts and wide open spaces, is at the heart of "The Joshua Tree". Sink into this gospel-tinged song, and you'll swear you can feel the gentle wave of the desert night air blowing against your skin in the midst of Bono's spiritual and philosophical uncertainty.
38Jimi Hendrix
All Along the Watchtower

The original version of this song actually happens to be one of my favorite Bob Dylan tunes, (though my knowledge of his catalog at this time is still limited.) With that being said, Hendrix's cover destroys the original in a master class of guitar playing frenzy; a swirling firestorm of notes that builds and builds until its glorious final eruption.
39The Rolling Stones
Gimme Shelter

The sound of free love and hippie idealism getting burried under the napalm shower of national dread. My opinion on the Stones is split, but this is definitely a crowning achievement or rock and roll emulating the apocalypse. Yet it's the single sliver of hope in "I tell you love sister/its just a kiss away" that reigns down as much impact as the punishing percussion and frantic harmonica.
40Utada Hikaru

Those who have never played "Kingdom Hearts II" will probably look at this selection with a vacant look on their faces. On the other hand, those of you who were fortunate enough to do so will recall the opening scene of that game and remember how this heavenly, infectious song perfectly encapsulated all of the swirling emotions you felt in preparation for your oncoming journey. Revisiting this years later, it's evident that "Sanctuary" didn't need a great game to hold itself up: This song is glorious in its own right.

Eminem takes a break from insulting celebrities and stabbing everyone in sight long enough to craft a brilliant tale about the unsettling consequences of obsessive celebrity worship. The sampling of Dido's "Thank You" as the chorus was a stroke of brilliance, and it's got one of the very few music videos that I actually think enhances the song rather than detracting from it.

Speaking of great female singers in electronic music, "Silence" features Sarah McLachlan in a mesmerizing vocal performance; less human than an intimidating yet shimmering angel who's radiant glow fills this song with divine power. The song has been remixed countless times into every electronic genre from trance to straight chillout, but the original with its Latin guitars, chanting monks, and MacLachlan's un-tampered divinity still leaves the biggest impact.

Beth Gibbons, who possesses as versatile and beautiful a voice as any woman I've ever heard, is the goddess of trip hop. At once perhaps her most fragile and most pure vocal performance, "Roads" submerges you into a pool of the deepest blue water and cleanses you through it's beautiful sadness.
44Simon and Garfunkel
The Boxer

"So what if our chorus is just a bunch of nonsensical lyrics? Simon and Garfunkle did it!" - What I imagine goes through the head of so many crappy pop acts today, (though perhaps assuming they listen to the folk duo at all is a bit of an overestimation.) The problem is, you're NOT Simon and Garfunkel. This powerful survivor's anthem famously took over a hundred hours to produce, and it shows with every plodding footfall.
45Kanye West
All of the Lights

The most prominent display of Kanye's opulent maximal-ism. The ultimate posse cut doesn't even use most of it's singers for more than a few lines; instead they're used to texture the light show with a blinding array of colors. Granted, Fergie drags this down a little, but the other thousand or so guest appearances more than compensate for her questionable entry. The beautiful piano intro is just icing on the cake.
46Neutral Milk Hotel
Holland 1945

The strangely affecting single on one of the THE great indie rock records of all time, "Holland 1945" has Jeff Mangum mourning Anne Frank and so many other souls lost in the Holocaust, but you couldn't tell that by listening to the upbeat melody and absolute bonkers combination of instruments.
47Michael Jackson
Bille Jean

If any song deserves to be called "pop perfection", it's this one. This thing has more hooks than a fishing boat, and let's be honest: There's no better song to listen to while running over hookers for money in "Gran Theft Auto: Vice City" than this one here, (and that's probably the case in real life, too.)
48Death Cab for Cutie
Tiny Vessels

A lot of people will openly show their adoration for Death Cab's "I Will Follow You Into the Dark". Ironically, it's that song's antithesis that conjures a far more powerful experience; a breakup song that shows the numbing consequences of masquerading uncaring relationships for sex. "You are beautiful, but you don't mean a thing to me." Refrains don't get much more brutally honest than that one.

Often overshadowed by the (nearly as brilliant) singles "Genesis" and "Oblivion", this twinkling song of spiritual synths showcases a stellar vocal display that's dextrous, fragile, and haunting. "I hate that you're leaving/so why don't you talk to me/You act like nothing ever happened but it meant the world to me." If those lyrics alone don't stir your heart, wait until you listen to hear sing them softly through the aether.
50Fleetwood Mac

While most of their greatest songs came off of the legendary "Rumours" album, it was their self titled that created their most beautiful moment. Every listen to this song makes you feel, as Charlie from "The Perks of Being a Wallflower" so perfectly put it, infinite.
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