Top 100 songs of all-time: 21-30

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.