Heartache With Hard Work

We’re entering the heights now. These are the songs that blow my world away every time I hear them, songs that make life worth living, songs that are as holy as the work of Michelangelo or Keats or Austen.

Spotify playlist with (almost) every song from this project.

1-10, 11-20, 21-30, 31-40, 41-50, 51-60, 61-70, 71-80, 81-90, 91-100

20. The Card Cheat – The Clash (1979)

London Calling is more devastating. Spanish Bombs is more tightly constructed. And either could have been my pick here. But at the end of the day, I have to go with my heart, and my heart tells me that punk rock has never risen higher, never said more, never spoken more truly than the final verse of The Card Cheat. Empires fall, the oceans recede, and all falls into dust. And yet, somehow, we find a way to rage against the dying of the light.

19. No Woman No Cry (Live) – Bob Marley & The Wailers (1975)

There are just a few songs in the world that can drive me to tears. The very best ones can also make me smile at the same time. This song pulls me in both directions, and fills me so completely with feelings that it’s a wonder I don’t burst apart every time I hear it. It’s relentlessly, impossibly hopeful. A salve for pain unending. It believes in a brighter tomorrow, against all odds. Because what else is there? After all, “my feet are my only carriage, so I’ve got to push on through.”

18. 32 Flavors (live) – Ani DiFranco (1997)

There aren’t many songs that leave me totally defenseless, no matter how many times I hear them. This is one of the few. A defiant stare. A blushing cheek. A prayer sent upward into the unyielding heavens. A poem written in the stars.

17. God Only Knows – The Beach Boys (1966)

Considered by many the greatest love song ever written, and it begins with the line “I may not always love you.” The second verse also starts with equal blandness: “If you should ever leave me, life would still go on.” But these cross-cutting statements provide the needed tonic against which the sweeping grandeur of the harmonies can be properly placed. The promise of a love universal—of feelings that can transcend this narrow plane of existence—is just too much for the mind to really comprehend. We strive for it, we need it, but we can only grasp it in the margins.  So in that final minute, when the harmonies layer infinitely deep on top of one another, it’s an invitation. It says: heaven lies somewhere over the horizon…let’s be worthy of entering once we finally get there.

16. The War Criminal Rises and Speaks – Okkervil River (2003)

The tension rises, the music begins to pound on the brain and Sheff’s voice crackles with intensity, bending and breaking, threatening to shatter at every moment. The singer makes no excuses, he cannot even cry, but it is clear that the mistake of thirty years ago has haunted him for every second of his life since. He does not ask to escape punishment, he only asks that those reading and watching to understand that he is not really any different from them. It’s a narrow sort of forgiveness, but it’s all that remains. And then, the camera reverses, to focus back on us, watching at home, comfortable and secure—certain that we would never fall so low. But do any of us truly know the madness in our souls? Is any of us truly prepared to face the evil that lurks behind our eyes?

15. Wish You Were Here – Pink Floyd (1975)

The opening is a bit of pure genius—the song itself coming on the radio and the singer strumming along in accompaniment. It’s such a simple thing, but it adds almost infinite layers of depth to the song. When the two merge back together, it achieves a level of tonal clarity that would have made Bach proud. And then the singer emerges: “So you think you can tell, heaven from hell…blue skies from pain…” and the song has already stepped outside the confines of rock and roll history. Eventually, the climax arrives, when everything collapses back upon itself, and all that remains is a plaintive wish for the impossible: “how I wish you were here.”

14. Fairytale Of New York – The Pogues (1987)

It opens with Shane MacGowan singing as no one else can: with a tenderness only matched by its raggedness. And then, even though you’ve heard it so many times before, you’re still completely unprepared for the way Kirsty MacColl’s voice emerges, triumphant, joyful, alive beyond words. As the verse unfolds and their voices intertwine you can almost see them, dancing together under the falling snow. It’s all there: the joy, the pain, the anger, the lost dreams, the hope, and the love. And on the final verse, when he sings “can’t make it all alone, I’ve built my dreams around you” there’s nothing left to do except weep for the sheer beauty of it all.

The tension in the song is, of course, whether to believe in the hope that they start out with, or whether to accept the pain of their conclusion. It would be a lie to pretend that you can simply wish away the bad stuff, but the sheer beauty of the song is the living proof that there must be something more.

What we hear in this song is the truest possible meaning of Christmas: a lament for the long winter, an expression of all the pain and suffering, the enduring human spirit. It speaks to our need to share the darkness with those that we love and the hope that this will somehow renew it, and allow another year to be born in the ashes of the past. One brighter, nobler, happier, and more secure. The need to believe, to hope against hope. That tomorrow we will run faster, stretch our arms farther…And one fine morning…

13. Years Ago – Super Deluxe (1996)

I lost my heart to this song years ago. More than half a lifetime ago, now, in fact. But it still feels every bit as close as it did back when it came through the radio that first time. It breaks my heart that this band never made it big, but I treasure those few years – back in the pacific northwest – when it felt like anything was possible.

12. God – John Lennon (1970)

It begins with one of the greatest lines ever sung (“God is just a concept by which we measure our pain”), and then he goes through the list of things he no longer believes in: magic, religion, politics, music…and then ends with:

I don’t believe in Beatles…
I just believe in me
Yoko and me
And that’s reality

And I just fall apart. Even after hearing it hundreds of times, it’s enough to split me into a thousand pieces. Because he’s right – that is reality. All the other stuff seems so important, but it’s when you find that one thing, that one person, it all clarifies. For John, all these things—God, magic, politics, music, even The Beatles—weren’t enough. They weren’t wrong, just incomplete. And this song is about the beauty that comes from being able to give them. The discovery that grand narratives only gain meaning once they’re refracted back through our own true realities. For him, that clarity came with Yoko. The way he felt about her, and the way that satisfied his need for explanation.

For someone else, it might be God, or The Beatles, or anything. The important thing is just that we find our own answer. That we not settle for life as it presents itself, that we dig down and settle into our true reality. And, hopefully someone to share it with.

11. Wildflowers – Tom Petty (1994)

I can still remember how I felt the very first time I heard it. I was in 8th grade and home sick with a cold. I borrowed the CD from my brother and hit play. And this song, this wonderful, impossible song poured out of the speakers. I sat back, full of wonder, and scared to move even one inch, for fear that it might break the spell and turn back into just another pretty song. So I loved it from the start, but over the years, those feelings have grown stronger, and more complex. Which is appropriate, because in lots of ways, Wildflowers is an old man’s song. A love that no longer speaks in terms of passion. A goodbye to someone you care about but know that you can’t hold onto. And with every year that passes, it grows just a little bit more poignant for me.

We’re getting close to the top of the list now, and it’s really difficult to draw a line between many of these songs. They’re all basically perfect–and the question is really just how many degrees of infinity I can try to differentiate.

Spotify playlist with (almost) every song from this project.

1-10, 11-20, 21-30, 31-40, 41-50, 51-60, 61-70, 71-80, 81-90, 91-100

30. Alabama Pines – Jason Isbell And The 400 Unit (2011)

A work of pure genius from one of the finest songwriters on the planet. It’s achingly sad: a perfect encapsulation of a disenchanted Southern spirit, of dead-end dreams and a weariness with the world. His voice on the chorus just brings me to my knees every time I hear it.

29. A Poem on the Underground Wall – Simon and Garfunkel (1966)

When there is nothing except the suffocating silence, a simple scrawl of four letters is all that’s left. It challenges us to mark the violence, to remain attuned to the impossibility of representation, to wrestle ourselves out of a stupor. The word scrawled across the advertisement is only poetry because it is there, in that place, at that time. What it means depends on who we are every bit as much as it depends on what it says.

In my heart of hearts, I can see the bold letters screaming ‘fuck.’ And yet, in that desperate plea, I can hear a whisper, a quiet voice reminding us that the word doesn’t matter. Salvation is not in the word; it’s in the act. Even more, it’s in the faith that lies behind the act. The faith that one word, scratched onto a subway wall, can still be heard. And that is, above all, faith in the power of ‘love.’

28. Coming In From The Cold – Delgados (2002)

If there’s an indie-rock Hall of Fame, this song should be the first inductee. It’s everything you could hope for. The bit where the final chorus seems to be fading and then Emma Pollock hits you with “we’re coming in from the cold…” is one of my all-time favorite musical moments.

27. Motorcycle Drive By – Third Eye Blind (1997)

It always drove me crazy that Third Eye Blind ended up with like seven singles from their debut record, but the best song never saw the light of day. The section at about 2:40 just leaves me feeling absolutely defenseless. It’s a glorious, careening, mad clatter of a song. A thunderclap rolling across you, shaking the entire world down to its foundations. And then you emerge in the aftermath, bathed by the cold light of morning—never so alone, and never so alive.

26. Antarctica – Antarctica Takes It! (2006)

The embodiment of everything lo-fi was ever meant to be, it exudes joyfulness without pretense and feature a sound so warm it could keep you comfortable on even the coldest of Antarctic nights. At times soft and tender, at others gloriously carefree, it careens through a number of different tones but never loses its pure beauty. An attack by a giant squid, sailors sinking to the depths of the frozen ocean, and yet somehow it retains a sense of wonderment as they exclaim “Antarctica, you stole our hearts!”

25. Tangled Up In Blue – Bob Dylan (1975)

The perfect Dylan song. The lyrics are brilliant: endlessly evocative without losing the sense of cryptic meaning. A set of interlocking stories, not connected in any obvious sense, but bound together by a shared sense of recurrence. This has all happened before and will all happen again. And yet, the eternal return is not simply a matter of repetition. The stories change, the characters shift, context blurs, and meanings shift. Time can’t be escaped, nor understood. It circles around us, forming memories and then taking them away.

The result is a song told in a series of moments, flashes of possibility. Is it the same man, encountering different women? Or vice versa? Or are these the same two souls meeting again and again, but unable to remember? Or are these simply random encounters with no connection at all, other than the simple reality that every encounter carries hints of all the others. And in the end, there’s nothing to be done except take another step down the road, see what waits beyond the next rainbow’s end.

24. Nightswimming – R.E.M. (1992)

At its core, this is an incredibly simple song: just that same piano loop repeating over and over with a few strings behind it. And yet, the way that Stipe paints the story within those confines is nothing short of magical. It’s everything and nothing. The single perfect memory that slips away no matter how much we resist. We hang onto the details—the picture turned around to face the windshield, the feeling of terror at your nakedness, where the moon sits in the sky. But the feeling of it remains ineffable. The longing, the undying faith, the certainty that if you just want it badly enough, you can stave off the passage of time. Inevitably, it fades, and “these things they go away, replaced by everyday.” And yet, there’s still a flicker, a whisper caught within the memory. A reminder of what it felt like to ask “and what if there were two?”

23. The Bleeding Heart Show – The New Pornographers (2005)

It slowly builds until just after the 2-minute mark when the guitars kick into gear, the pulse quickens, they go up one more notch, and then Neko Case belts out “we have arrived too late to play the bleeding heart show” and your heart stops. Every time I come back to this song I’m astonished once again by just how good it is. Just listen to the drums in the bridge, or the guitar riff that transitions from the “oooohs” to the final “hey la” bit. It’s gravity-defying.

22. The Lethal Temptress – Mendoza Line (2005)

It’s about just barely staying afloat, holding onto the dreams you once had, but knowing deep down that you probably won’t see them happen. And still, knowing that you’re never going to get what you wanted,  you struggle anyways. To find a way to create some new dreams, without glamour, fame, or a silly idea of perfection, but which will be all the more beautiful because they have been tempered by pain. “Just one more glass of gin before I fall back in to the arms of the lethal temptress.” It’s a devastating song.

21. Graceland – Paul Simon (1986)

It opens: “The Mississippi Delta was shining like a national guitar / I am following the river down the highway through the cradle of the civil war.” That is pure poetry, evocative and beautiful. And it establishes the multi-layered themes. Traveling with the one who loves your most truly (your son) on a pilgrimage to the roots of rock and roll, seeing the country that tore itself apart and slowly (very slowly) began to heal itself over the centuries, and thinking about your own world being blown apart. The deep, intense sadness. The slight sense of bemusement and disbelief. The realization that you knew all along but just couldn’t quite admit it. And the falling down of walls that you have tried desperately to erect between your interior and the world outside. There aren’t answers here, but there really couldn’t be. The important thing is the searching, not what you will find.

Many of my favorite songs of love and loss here. From the passions of youth to the quiet resignation of age, and everything in between.

Spotify playlist with (almost) every song from this project.

1-10, 11-20, 21-30, 31-40, 41-50, 51-60, 61-70, 71-80, 81-90, 91-100

40. Anthems for a Seventeen Year-Old Girl – Broken Social Scene (2002)

A beautiful song, with the sort of aural landscaping that makes people want to reference Pet Sounds. But there’s something much else going on, too. That banjo, the strings, the deeply flanged vocals…and the way it creeps up on you until you realize you’re completely encased in sound and totally weightless. “Park that car, drop that phone, sleep on the floor, dream about me.” Yep.

39. September When It Comes (Feat. Johnny Cash) – Rosanne Cash (2003)

A beautiful, haunting song, sung as a duet with her dad; one of the very last recordings he ever made. A song about the anticipation of loss, sung with a man all too aware of his imminent mortality. When their voices join in the second half, the combination of the gravel and dust of his voice with the smooth sheen of hers is life-changing.

38. It’s the Same Old Song – Four Tops (1965)

It’s got that great driving Motown beat, some beautiful harmonies, and everything else you’d want from a 60s chart-topper, but there’s something else, too, almost ephemeral. It’s a sad song, but powerful, too. It is such a universal message, and performed so brilliantly that it’s almost a mantra. It’s my favorite song that ever came out of Motown. And the whole thing was written, performed, and pressed in just 24 hours!

37. Silent Treatment – The Joy Formidable (2013)

If you went into a laboratory to design a song for me, you could hardly do better than this. A gorgeous double-tracked voice, backed by a delicate acoustic pluck, rising up and then falling around a single note…that’s what it takes to make my heart sing.

36. Tear-Stained Eye – Son Volt (1995)

Jay Farrar has written more than his share of beautiful songs. This is his absolute finest. The banjo solo, the pedal steel, the lyrics, his voice. It’s a masterpiece.

35. No One Will Ever Love You – Magnetic Fields (1999)

Stephin Merritt has described this as an attempt to sum up in a single song the entire experience of listening to Fleetwood Mac’s Tusk album. And you’d have to label it a smashing success. It’s wistful, melancholic, dusky, smoky, and wholly captivating. Plus, “where is the madness that you promised me?” is an all-time great lyric.

34. I Am John – Loney, Dear (2007)

The whole song is a giant, escalating spiral as verses double back and trample on one another and the chorus jumps out whenever it has a chance until the end when the falsetto emerges and it is repeated as a final running-over-itself refrain. Remember that scene at the end of Back to the Future where Doc says “where we’re going, we don’t need roads”? He was talking about this song.

33. Are You Out There – Dar Williams (1997)

There have been many great songs written about the power of radio, but I think this is the best. The drums provide the momentum, but it’s her voice that carries the show. When she sings about staying up to see the dawn, you can almost feel the light creeping up over the horizon. And her, crouched by the radio, listening as the songs come through, in all of their crackly beauty.

32. Emmylou – First Aid Kit (2012)

It’s an ode to love, companionship, partnership, and a long history of music. Their voices dance around each other, the guitar sliding around them without the tiniest bit of friction. And it’s all tied together by one of the greatest choruses in musical history—made all the better by those couple dipping notes on the guitar that immediately precede it.

31. Salome – Old 97’s (1997)

Packed with emotion without being overwrought, it showcases Miller’s wonderful voice, with just enough twang to keep you honest. Lovesick, heartfelt, and beautiful. It’s perfect.

Today we have a whole bunch of songs from the 90s and early 2000s, along with the only pre-1964 track to make the list. Though as I write that, I realize that I really should have thought more seriously about including classical music. Bach for sure would have been on here. Maybe some others. Oh well…

Spotify playlist with (almost) every song from this project.

1-10, 11-20, 21-30, 31-40, 41-50, 51-60, 61-70, 71-80, 81-90, 91-100

50. Black Synagogue – Angel Haze (2014)

At her best, Angel Haze is probably my favorite rapper in the world. And this is very much her best. “Black Synagogue” is full of rage and empathy and she spits it all out at 150 MPH.

49. Last Stop: This Town – Eels (1998)

Electro-Shock Blues is one of the darkest, most painful albums of the past few decades. It’s also one of the most hopeful. This song is the linchpin, the heart of its duality. It’s a death rattle, a wish for one last night with his sister—who had recently committed suicide. A chance to share all the impossible beauty of the world one last time. It’s driven by that truly gorgeous melody, punctuated by glitches and scratches, which makes you believe that anything is possible. That even in the face of the most tangible tragedy, there is still something else out there. A reason to live.

48. Birdhouse In Your Soul – They Might Be Giants (1990)

Flood is easily my favorite TMBG album. I was first introduced to the band via Tiny Toons, as I’m sure was the case for many others of my generation. But it was a couple years more before I actually heard the whole album. And it was kind of a eureka moment, actually. Like any kid, I enjoyed a good goofy song now and then, but I still assumed that there was a clear dividing line between ‘real’ music and novelty songs. Flood blew that distinction to bits–showing me that silliness could live side by side with philosophy, and that simple could also be incredibly complex.  There’s no song that exemplifies that more than this one. Clever, wonderful, deeply emotional, light as air.

47. Emma Blowgun’s Last Stand – Beulah (1999)

I love the intro to this song. Two minutes of slow unfurling, and then those horns kick in, and it feels like the first day of spring after a long cold winter.

46. Anti-Manifesto – Propagandhi (1993)

Punk rock will never die, because one of its most fertile subjects is the death of punk rock. It’s an eternal positive feedback cycle of decline and rebirth. And it’s never been better executed than here. How to Clean Everything is not only the best punk record of the 90s; it’s one of the best records of the 90s, full stop.

45. Idyllwild – Trembling Blue Stars (2007)

“A girl whose favorite thing is snow – snow and being alone.” The whole song is gorgeous, but this is the line that absolutely devastates me. Somehow, those eleven words manage to build an entire universe. I see her sitting by the window, watching the snow fall. I sense the depth of her love, but also the weight of her loss.  The world is painted white and she curls up tight, trying not to think about what waits beyond that blanket of snow.

44. Blue Train – John Coltrane (1958)

The first time you hear this song, it already feels like an old favorite. Like Coltrane is simply jogging your memory, calling to mind a melody you’d long since forgotten. And with each subsequent listen, that feeling only grows. And yet, its closeness defies comprehension. It pierces us on a level that exceeds the conscious mind–a realm of pure mathematics and impossibly complex equations. It speaks a truth that we can feel without ever quite understanding.

43. Mayonaise – Smashing Pumpkins (1993)

When I discussed If You Leave earlier in the list, I said that it struck me as the definitive song of the 80s. In which case, I think Mayonaise one might count as the definitive song of the 90s. It clearly surfs the wave of Nirvana-driven alt rock, but draws heavily on many of the other traditions that dominated the era. Loud/soft dynamics, a shoegazy wall of guitar noise, a pitch perfect melodic structure. It’s all here.

42. Taxi Ride – Tori Amos (2002)

When I made my list of the top 50 songs of the 2000s, I inexplicably left this one down in the honorable mentions. What on earth was I thinking? This is an all-time great song, the work of an artist at the height of her powers, whose ability to balance piano and voice is on the same measure with Raphael’s ability to balance color and shape.

41. Yulia – Wolf Parade (2010)

“They flip one switch at mission control, and I’m never coming home.” The madness of the endless cosmos, the realization that you have already died but are left to drift alone in the dark reaches of spaces – and that there is only one person far behind who will think of you. All tinged with a sense of awe to simply be out there. What a horrible, wonderful, deeply sad way to die…

Songs from a fairly narrow time band of the mid 90s to early 2000s, with three very different songs of the late 60s to balance things out.

Spotify playlist with (almost) every song from this project.

1-10, 11-20, 21-30, 31-40, 41-50, 51-60, 61-70, 71-80, 81-90, 91-100

60. The Day John Henry Died – Drive-By Truckers (2004)

Jangly, swaggering, big, boisterous. Triumphant even while it’s depressing. Everything that John Henry was meant to be.

59. Love Me, I’m A Liberal – Phil Ochs (1966)

He is sarcastic and caustic, frustrated to no end by the apathy, the self-satisfied attitude of an America which claims to uphold fundamental ideals but fails to ever do anything about it. How could a society supposedly devoted to equality and justice stand for the continued existence of crushing poverty, segregation, the Vietnam war, and so on? As he says: “In every American community, you have varying shades of political opinion, and one of the shadiest of these is the liberals. An outspoken group on many subjects. Ten degrees to the left of center in good times. Ten degrees to the right of center if it affects them personally.”

58. Head Rolls Off – Frightened Rabbit (2008)

This is the return home, where everything comes right. When we discover that all those things we used to look for in God are now reflected back in the world around us—in the eyes of a million hopeful souls, living, loving, singing, dancing, touching hands, writing stories. And this song is the mirror for it all.

57. Homesick – Aberdeen (2002)

Pastoral and effortless—a song that floats in the clouds. It starts quietly and her voice drifts along, full of gentle longing, barely skimming the surface. But my absolute favorite moment is toward the end, when all the sweet tension fractures and everything bursts into light.

56. Photobooth – Death Cab for Cutie (2000)

It’s the epitome of the stripped down indie rock revival that eventually far overstepped its bounds: the literate and boyish charm, the absolutely perfect pop sensibilities. I’ve grown a lot less enthused about this sort of thing over the years, but there is absolutely no denying the vitality of this song.

55. My Name Is Jonas – Weezer (1994)

Loosely based on Lois Lowry’s The Giver, this is one of the all-time great Side One, Track Ones from a debut record. The transition from that opening acoustic riff to the wall of guitar noise is the sound of an entire generation snapping into focus.

54. What a Wonderful World – Louis Armstrong (1967)

I think you could make a strong case for Louis Armstrong as the single most important artist in American history. And this song is a suitable capstone to the embarrassment of riches that is his musical career. In the hands of someone less capable–someone who had been through less, someone without the depth of his experience and care–it could have come across as overly simplistic, even naïve. But in the hands of Louis Armstrong, it’s nothing short of religious.

53. Ruby Tuesday – The Rolling Stones (1967)

It should be no surprise that my favorite Stones song is the one where they sound the closest to the Beatles. I know a lot of their fans didn’t necessarily love their trend toward the baroque during this period from 66-68. But for me, it’s my favorite version of the band. And Ruby Tuesday is definitely my favorite song of the bunch.

52. Toxic Toast – The Mighty Mighty Bosstones (1994)

It’s fitting that my relationship to this song is so fully defined by nostalgia. Much like Dicky Barrett, I can feel a sense of loss at the relentless pace of life—which separates us from old friends and the carelessness of youth—without necessarily wanting to go back. And one of the wonders of music is the way it can bridge the years, and for four minutes remind you how it felt to be a very different person, in a very different place and time.

51. Heart Shaped Box – Nirvana (1993)

I went back and forth between this one and Smells Like Teen Spirit maybe a dozen times (with a brief stop at Where Did You Sleep Last Night). But at the end of the day, it had to be this one. Teen Spirit defines Nirvana, and it is a firestorm of a song, but it also feels just the tiniest bit false. Like it’s been filtered through a bit of studio wizardry to make it sound just that big. But Heart Shaped Box is a window directly into the soul of the artist. Crystal clear, with all the pain and madness that it implies.

Spotify playlist with (almost) every song from this project.

1-10, 11-20, 21-30, 31-40, 41-50, 51-60, 61-70, 71-80, 81-90, 91-100

70. Like A Prayer – Madonna (1989)

A rumination on Catholic guilt, the boundlessness of human sexuality, and the power of pop music to literally move the world. It was attacked as anti-religious, and certainly it speaks from a critical vantage. But those criticisms are also clearly marked by a deep sense of belonging. Madonna is playing with the traditions, giving them new life and new voice, forcing them to speak in new languages. This is essentially a gospel song, and there’s no hint of appropriation in that act. It’s a provocation, but one that absolutely believes in the underlying power of faith.

69. Julian – Say Lou Lou (2013)

The harmonies are exquisite. It’s got the lush production that has characterized Swedish indie pop for the last decade, married to the atmospherics of classic Fleetwood Mac. It’s a heady combination – the sort of song you can listen to on repeat for hours.

68. We Found Love – Rihanna (2011)

Pop music is designed to be ephemeral. Even the best of it often fades away quickly. It’s the rare gem that not only lasts but gets better and better with time. We Found Love is such a gem. Its hopefulness and beauty have transcended the momentary and become universal. People will still be dancing to this song a hundred years from now.

67. Samson (original version from Songs) – Regina Spektor (2002)

A brief glimpse into that other world: where Regina and Samson live a quiet life together, where Samson never tears down the walls, and instead just shares a quiet night together with the girl he loves. It really speaks to me because, well, given the choice: epic fame or a few happy years of love, I would happily fall into the mist with a pretty girl and her piano. I wonder how many of the larger-than-life heroes of our past would wish the same.

66. Heroes – David Bowie (1977)

Music, at its best, is an exercise in the limitless compassion of the human spirit. It’s an invitation to become another, to see the world in a new light, and to discover the magic of our ceaseless differences. And there aren’t many examples of a song more successfully engaging this project than Heroes. It unspools slowly, delicately laying each piece, all so that when the madness eventually takes over, the whole thing will be strong enough to weather the storm. Maybe.

65. No Rest for the Weary – Blue Scholars (2005)

“Hold your head high soldier, it ain’t over yet. That’s why we call it a struggle, you’re supposed to sweat.” This song is all about reveling in the rhythm of life, over a smooth beat and insidiously beautiful backing track that worms its way deeply inside you. It’s insistent, nagging, powerful. Angry but honest in its hopefulness, too.

64. A Summer Song – Chad and Jeremy (1964)

This was my favorite song in the entire world when I was 12 or 13. I would sit in my room on rainy Washington days watching the streaks run down the window and dreaming of a time when I could experience something this bittersweet. Sure, that’s a little weird, but the song is so gorgeous and heartbreaking, surely you can understand why.

63. Are You There Margaret? It’s Me God – The Lawrence Arms (2006)

It’s chaotic but measured, hardcore and honest, a three minute firestorm filled to the brim with slashing chords and screams and passion. The chorus is out of this world, but the absolute best part is the bit at the end, after the final chorus, when you think that the song is starting to fade out but they come back one last time to punch you in the gut.

62. Unsatisfied – The Replacements (1984)

If you wanted to condense the entire Replacements catalogue into a single line, it would have to be “Look me in the eye and tell me that I’m satisfied.” This is a shambling song, meandering, drunken, sloppy. It’s also beautiful.

61. The Henney Buggy Band – Sufjan Stevens (2006)

An outtake from the Illinois record…and the best song he’s ever recorded. Just think if he had never got around to releasing all those extras. It would be like if The Beatles had left “Ticket to Ride” buried somewhere in the Abbey Road archives.

With this installment, we’re living almost entirely in the bubble of late 90s/early 2000s white people rock. And the one major exception is a Velvet Underground track that in many ways could count as the first mover of the wave that would finally crest a few decades later. Basically, like I said at the start: I make no claim to objective valuation here. This is just the stuff I love.

Spotify playlist with (almost) every song from this project.

1-10, 11-20, 21-30, 31-40, 41-50, 51-60, 61-70, 71-80, 81-90, 91-100

80. Spectacular Views – Rilo Kiley (2002)

It’s a huge, overwhelming song – an anthem built out of fireworks and smiles. It’s the wide-eyed innocence of youth, the certainty that everything is still possible, and all you can say is “It’s so fucking beautiful!” And in that moment, everything in the universe makes sense. That’s just all there is to it.

79. Stephanie Says – The Velvet Underground (1968)

The simplest, most beautiful song from a band that radically redefined the genre of simple, beautiful songs.

78. Parking Lot – The Coathangers (2007)

Sleater-Kinney meets The Replacements. With one of the all-time great rock and roll screams.

77. Stay – Lisa Loeb (1994)

The first song to ever hit #1 before the artist had signed a record contract. It’s a quintessential bite of the mid-90s, with a perfectly blended mix of earnest and world-weary that made it fit so perfectly into Reality Bites. Loeb sings with a breathlessness that makes each sentence bleed into the next, and conveys precisely how it feels when the world seems to be spinning out of control. It’s also got a wonderful bit of self-referentiality in “I turned the radio on, I turned the radio up, and this woman was singing my song” – which is precisely what happened for all those who fell in love with this song once it hit the radio.

76. Three Rounds and a Sound – Blind Pilot (2008)

It takes a lot of guts to write a song whose mission statement is to become an ‘our song.’ But it works because they understand something that’s so often missed in the endless parade of love songs that march across our speakers each year. And that is: the single most romantic thing anyone can ever say is “you know me.” There’s beauty in the world, laughter, support, care. But it all comes down to this. I know you, and you know me, and that’s what it really means to be in love.

75. Graceless – The National (2013)

Berninger’s distinctively smoky voice, the tightly wound guitar lines, and above all that insistent drumming. And when it all comes together, it is sheer perfection. The final minute or so is absolutely, relentlessly good.

74. Zolpidem – The Sinister Turns (2006)

Beautiful, funny, intelligent, and full of enough pop charm to make the even the hardest heart blush. It’s irresistible in the way only the very best songs can manage – where you can hear two seconds and instantly need to listen to the whole thing.

73. Untrustable Part 2 (About Someone Else) – Built to Spill (1997)

One of several songs on this list with a wonderfully precise observation about the nature of God (in this case it’s “God is whoever you’re performing for,” which is both brilliant and succinct). Built to Spill were at their best in the late 90s and this song is the peak—stately, sprawling, and stunning.

72. Fake Plastic Trees – Radiohead (1995)

Radiohead went on to make a number of incredibly important records, which played a significant role in shifting the trajectories of what rock music could mean going into the 21st century. And I’m glad for it all. But still…a part of me laments that they never dug down into this well again. It’s not groundbreaking, by any stretch of the imagination. It’s just a gorgeous melody, ringing with the perfect clarity of a brand new dawn.

71. Grace Cathedral Hill – Decemberists (2002)

It glows like the porchlight of a house in the woods in the deep mist of a cold evening. The Decemberists were always at their best making dreamy-chamber-pop, and never more than on this track. I still am blown away by the simple beauty of: “are you feeling better now?”

A bunch of love songs today, which run the gamut from completely specific to wholly transcendent.

Spotify playlist with (almost) every song from this project.

1-10, 11-20, 21-30, 31-40, 41-50, 51-60, 61-70, 71-80, 81-90, 91-100

90. Crimson And Clover – Tommy James & The Shondells (1968)

That descending guitar riff that closes out each line of the song is like manna falling from the heavens.

89. Take On Me – A-Ha (1985)

The 80s were a grim decade in many ways, musically not being the least among them. But one thing it provided was a backbone of delightful dance music, which could be universally enjoyed without thereby being forced into a lowest common denominator drabness. Take On Me is one of the finest examples of this effect. It’s pop music precisely the way it should be done—a simple chord structure that speaks directly to the heart, with a surprisingly complex underlying melodic system that stands up to decades of close listening. The result is a song that sounds as fresh now as it did in 1985.

88. World Tour (Weezy, Wale, Dre) – Brenton Duvall (2011)

Picks out the chorus of Wale’s “World Tour,” and supplements it with raps from Lil’ Wayne and Dre’s “Forgot About Dre,” placing each of them against a shimmering, beautiful, insistent background of electronica. The resulting creation sounds totally distinct and organic – it’s almost impossible to picture these pieces in their original form. The Dre part, in particular, is utterly different. What came off as aggressive and petulant when backed by Eminem now sounds strangely humble, even hopeful.

87. Aaron & Maria – American Analog Set (2001)

A modern love story, quiet and precise. The march is measured, the guitars gentle but cool to the touch, and the drumming the soul of restraint. And it’s summed up perfectly in the refrain: “loving you is just enough, cause no one gives a fuck about us.”

86. Who’ll Stop the Rain – Creedence Clearwater Revival (1970)

Released in January of 1970, in many ways this song marks the turning point from the optimism and endless possibility implied in the music of the 60s to the retrenchment and dissolution of the 70s. The lyrics are reflective, drawn vaguely enough to speak universally, but clearly meant to speak to the rising horror of the Vietnam War – and to the strange brew of music and counterculture and self-immolation of Woodstock.

85. Hallelujah – Jeff Buckley (1994)

You don’t need me to tell you anything about this song. Yes, it’s overused in film and TV. Yes, it walks a very fine line between precocious and precious. But c’mon. Pretend you’ve never heard it before and listen with fresh ears. It’s an astonishing performance, one that more than pays off any debts incurred by overzealous filmmakers in need of a soundtrack for heartbreak.

84. Give Me Love (Give Me Peace On Earth) – George Harrison (1973)

Of all them, I think George ended up with the most successful post-Beatles career. This song narrowly beat out three or four others that could easily have also made the list. It’s a very simple song, with a pretty basic chord progression and a repeated lyrical refrain. But that underlying structure is just a delight. It’s soulful, warm, light, and sparkling.

83. Immunity – Jon Hopkins (2013)

Love is the longing for the half of ourselves we have lost.

82. Layla – Eric Clapton (1970 and 1992)

This song wouldn’t quite make the cut in either its original form (searing guitar and extended piano coda) or its bluesy, unplugged update. But the combination of the two iterations—the way they play off one another, adding depth to each iteration, exposing the limits of any singular perspective—elevates the track to a new level, and makes it a worthy addition to the list.

81. If You Leave – OMD (1986)

To my ears, this is the defining song of the 1980s. The decade featured plenty of songs that sold more records (If You Leave was a hit, but not a record-breaker by any stretch), and a few songs that were better. But if you took all the distinctive features of the 80s, stuck them in a centrifuge to strip out all the mediocre variations, you’d get this track: the pure distillation of what was good about the decade. Given that, it should be no surprise that the song was written specifically for the closing scene of a John Hughes movie.

As a lover of music and as an obsessive maker of lists, it’s kind of surprising I’ve never put in the effort to construct this ultimate list before. But one of my friends recently sent his own list and it got me to thinking about what I’d put on mine. And, as the owner of a blog where I get to ramble on endlessly about the music I like, it seemed like a good excuse to engage the project.

The only rule is ‘one song per artist.’ And it’s important to make clear that this is simply a list of my personal favorite songs. Plenty of all-time classics are missing here, while some relatively inconsequential ones make the list. I make no claim that, for example, “A Summer Song” is objectively superior to “What’s Going On.” I just (perhaps inexplicably) enjoy the former more.

As a result, this is a list that tilts fairly heavily toward my own personal history. I was a kid who grew up listening to oldies radio stations, joined up with modern music in the mid 90s once boys with guitars were back in style, and then slipped seamlessly into the indie rock bubble of the early 2000s. Over the years, I’ve worked to expand my musical horizons a bit, bringing in more hip-hop and jazz, more music from women, more work in experimental genres. But at the end of the day, the ‘sad boys with guitars’ groove is carved pretty deep, and that’s going to be reflected in the list.

Maybe someday I’ll work on a different list of the 100 most important songs in modern musical history. But for now, this is just my personal favorites. For better and for worse.

Spotify playlist with (almost) every song from this project.

1-10, 11-20, 21-30, 31-40, 41-50, 51-60, 61-70, 71-80, 81-90, 91-100

100. Waitin’ for a Superman (Remix) – The Flaming Lips (1999)

The base of this song is a lovely rumination on the limits of human achievement and the ways we struggle to hold everything together in spite of those limits. The remix adds a beautiful sheen, which lets the underlying hopefulness shine through more clearly.

99. Daydream Believer – The Monkees (1967)

My favorite detail of this song is that the original lyric was “now you know how funky I can be” but the record execs insisted that it be changed to ‘happy’ because funky might make people think about a bad smell. The line, as changed, doesn’t really make sense, but somehow it works better this way.

98. Let’s Get Out Of This Country – Camera Obscura (2006)

I absolutely adore this song. It’s a revelation, almost a religious experience. The joyfulness, the way that opening guitar riff signals the rush of good feelings and hope at a new day. It deserves to be played on a sunny day when you can throw all your cares to the wind and just enjoy yourself.

97. It Ain’t Me Babe – The Turtles (1965)

Folk-rock covers of Dylan songs were a real cottage industry for a couple years there in the mid-60s. This song is the best of the bunch to my ears—even bettering the wonderful Mr. Tambourine Man from the Byrds. Part of the joy comes from the radical restyling of the song. There’s a raucous quality to this version, which plays nicely with the underlying bitterness of Dylan’s lyrics.

96. Source Tags And Codes – And You Will Know Us By the Trail of Dead (2002)

An all-time great album-closer. It rises above the noise and chaos, like some sort of glorious rock and roll city on the hill.

95. Light My Fire – The Doors (1967)

Growing up, The Doors were the one band that everyone in my family loved. And this song more than any of the others. To me, this is the soundtrack of long family road trips. It’s the song that we played at my grandfather’s funeral—because we all loved it and who cares what it’s ‘really’ about. I completely understand why a lot of people dislike this band. But for me, they’ll always sound like home.

94. Modern Girl – Sleater-Kinney (2005)

This almost certainly isn’t the best Sleater-Kinney song. But it’s my favorite. It starts out pretty, and then builds and builds into that final minute, where they make a joyful noise unto the world.

93. The Con – Tegan and Sara (2007)

Tegan and Sara’s definitive statement of intention. A rambunctious pop masterpiece, packed with hooks and synths and unadulterated joy. It’s charming beyond belief, sensitive, swaggering, anxious, and compassionate. Everything you could ask for.

92. With Or Without You – U2 (1987)

Reasonable people can disagree over precisely when U2 tipped over the edge from great rock band into self-parodying musical commodity. But those first few albums really were glorious explosions of rock fire. And I’d say the absolute peak was right here, in this quiet, confident, achingly pure song about the nature of sacrifice. It somewhat notoriously deploys the I–V–vi–IV chord progression, but does so in the service of a genuinely sophisticated melodic development. Rather than deploying a simple verse-chorus-verse, it works a lot more like a classical composition, with a number of themes that interlink and repopulate in some surprising ways.

91. Howl – The Gaslight Anthem (2012)

Designed as a sort of postscript to Thunder Road (spoiler alert: Thunder Road will be higher on this list). Once again, there’s a girl whose dress waves, a guy with a car offering to take her away. But it’s pitched toward the future, to a Mary who said ‘no’ to the first offer. She stuck around, went to school, and made a life for herself. And now our hero sends out a final missive: you know where you can find me, and all those plans I made might still have some life in them. It works because it’s audacious, it works because it feels real, and it works because Fallon absolutely sticks his lines. For a band that’s devoted to the idea that the radio really might just save us, this is the shining moment where it feels absolutely and completely possible. So when he sings “I waited on your call and made my plans to share my name” there’s nothing you can do but hope along with him.