The 20 Best Songs of All Time
If you're anything like me at least, by which I mean if you're exactly like me... like, *exactly* like me
There was a viral prompt going around on Twitter at some point last year, to name the 20 songs that define you the most or whatever. I’m pretty sure no one enjoyed reading anyone else’s list, but everyone definitely enjoyed making them.
You’ve probably seen the meme about being surprised how much you’re into the playlist you just made of all your favorite songs. So this is going to be that, embarrassingly enough. But I’m also going to briefly make a case for all of these. Hopefully it will form some sort of reference point; I write about music that I like on here, but you all have no idea where I’m coming from. I think we all have music that we think of as our “true north” or whatever: music that you put above everything else even if it’s uncool or only seems particularly meaningful to you. Here’s mine.
In no particular order…
I’ve written about it before, but The Kick Inside was one of the most formative influences for me after college, which is to say, I was lost, and suddenly felt incredibly found in this album, which for me brings together elements of things that I had always felt could belong together, but never did in the music I grew up with: the modernity of the pop song, musical theater or theatricality in general, narrative, all this fantastical, wide-eyed dreaming positioned right next to cutting truths about the impossibilities of human desire. And musically, this album reminded me that piano can be cool, when you have this kind of chordal mojo. The first two chords of Wuthering Heights are part of this throughline of staggering modulatory weirdness in pop songs that you can follow from John’s crazy opening chords of I Am the Walrus to Elliott Smith to Radiohead to… well, most recently, Charli XCX.
I think people are catching on to this one now, as Britpop type stuff starts to come back into fashion. Of course, Prefab Sprout has never truly been part of any trend, and I don’t expect them really to ever be. But I don’t know. I still think this song could go the distance as a hauntological 2020s streaming services hit, in the way that Dreams or Running Up That Hill briefly captured everyone’s imagination. I ran into this song in college and it started to divert me on a path away from contemporary indie rock and towards some things that had been left behind in the 1980s. And rhythm sections. Check out that drumming—it’s so fucking explosive. I think this is the closest Paddy McAloon got to a pop song that wasn’t really doing anything weird, and as much as I love his weirdness, I wonder if he had been just a tiny bit more straightforward if he might have enjoyed more success back then. Probably not though, people just don’t know!
“Save Me” and the rest of the Magnolia soundtrack was of course my entry point to Aimee Mann’s music. But discovering Whatever changed my life. This album has such an incredible feeling of “who gives a fuck, let’s do it anyway”: the otherwise formulaic rock band arrangements are juiced up with the coolest and weirdest guitar parts you’ve ever heard, and then they fully take a break every now and then to do a few bars of “jazz combo” (the bridge in this song) or “tin pan alley” (Way Back When). And the Bob Clearmountain mix! So much energy! The nostalgia cycle has brought back the 90s in the form of shoegazy, drum machine-y, sludgy garbage water (oops, I meant to say: beautiful music1), but what about this weird nascent period as the big 80s snare gave way to a bassier, punchier full kit sound, and the previously supercooled, chorused-out guitars suddenly heated up for a minute.
This isn’t the best or even necessarily in the top 10 best Michael Penn songs, but it is the one that will instantly cheer me up when I put it on. The aforementioned Aimee Mann said that when she heard it on the radio, she thought, wow, someone actually got through with a real song. And that’s the feeling here: first, what the hell, and then, by the chorus: yeah! It’s the Beatles! Anyway, they’re married now—perhaps if you ever hear an artist you like on the radio, you should just slip into their DMs?2
For me I like to think of this song whenever what I’m writing is feeling too complicated. No Myth is about the level of complexity anyone should be aiming for, in pop, which is to say, not too much, but enough that you might attract serious romantic interest. Sorry, what was I saying?
Feels truer than most songs. Goes harder than most songs. Maybe the best “power pop” song, for my money. And I don’t have a lot of money!
I got interested in rhythm sections, and how a band goes together, and then at some point deep into that (I’ve never really emerged, for better or worse) I encountered Steely Dan, or I guess re-encountered, as I’d never really understood them before. And they have the best rhythm sections, of course. But I also started to hear the tragic quality of the various losers and assholes depicted in the lyrics. Sometimes, or maybe more often than not the asshole is the singer. And there’s an appeal to that, but My Old School does something different. The story about youth and college and authority is exploded into this massive feeling of exhilaration. Scott Miller wrote that it could get him out of “deathbed depression and back to loving life with mechanized efficiency.” I wonder if that’s why: it makes me feel as alive as I did when I was twenty one or two. I guess it’s a feat of nostalgia, maybe, but the talk of California tumbling into the sea makes me look to the future too, and from here, the world of the song, it doesn’t seem all bad.
I’m amending my Beatles pick from “And Your Bird Can Sing” to this for one reason: this is one of the few songs I can sing, out loud, unaccompanied, on command. What does that prove? I’m not sure. I think it locates it closer to the first songs, you know, when you’re a human and it’s like 300 BC and you’re just walking around and making up a song to yourself. Of course, then it has some of the most sophisticated guitar and drum counterpoint, like ever, but none of that feels complicated, it just feels awesome. “When I was a boy… everything was right.” Yeah… that’s the gist of it!
Kings Of Convenience - I’d Rather Dance With You
Alright, now we’re really getting into the music of my youth. I showed this song to some friends when I was nineteen or so and both of them were offended by the song’s premise: “I’d rather dance with you than talk with you”. Surely you want to get to know me too? I disagreed then, and I still do. I mean, sure, you can read it in a sleazy way, but I think it’s more about wanting to avoid the artificiality of making small talk. We invented dancing and parties to get around that sort of thing. If you’ve already been dancing with someone all night, then you can get straight into the heavy stuff. I mean: heavy conversation. If all you want to do is trade book recommendations (that none of us, in the 2020s, have actually finished reading) then what are we doing here?
A great r&b pop song about life. Some great lines: “This what I want / look at what it did to me” and “This is what you want / this is what you get instead”. All of that existential moaning, and it still manages to cheer me up.
I think Rocketship were about ten years ahead of their time. They would have fit right in in 2009 or so. How do I know this? Because hearing them for the first time felt like coming home, and the music that feels like home to me is mostly from about 2009, of course, when I was a pre-teen, of course. This music endures better than anything from the actual 00s, though, probably owing to its not-so-fussy production and loose feel. And those melodies, god, those melodies.
Listen, with Bacharach it’s the idealism I’m attracted to, not just in the lyrics—which imagine, and therefore create a comforting place where you can hang your hat and forget your cares—but in the music, which imagines towering spires of major-seventh chords, orchestra and small combo band all hitting together on those downbeats. Probably Steve Gadd on the drums. Anyway, this may be the closest we’ve ever come to utopia—not in reality, of course, just in our imagination.
This song has THE BEST chorus of all time. THE BEST. There’s really no discussion. “See how we grasp at the stars!”—yeah, man. It’s fucking unbelievable.
Scott Miller’s masterpiece. It feels hugely influential, and it was to Aimee Mann at least, but I wonder if this record and song didn’t influence lots of other artists of the time. It sounds to me like a lot of things that would come later, albeit not so much in the production. Arcade Fire could have written this song, and had a hit with it, for instance. The melody and sentiment of “I’ll bet you’ve never actually seen a person die of loneliness” was staggering to me when I first heard it. I was on a road trip and just wanted to hear it over and over. And the remoteness of “Inverness”—in Scotland or California—which is a perfect proper noun to put in this introspective song: it sounds like “inwardness,” and the inverse of something. Scott goes investigating the contradictions in his soul, and finds nothing there that isn’t cliched. But maybe the cliches can be piled up into something new?
I’m realizing there’s a common thread in a lot of my favorite songs, which is imagining some kind of utopian future, or at least the feeling of possibility. I think that’s the “feeling” that’s “hard to describe” in this song. If we don’t have that, it’s hard to keep going. So maybe that’s what I’m always looking for in music. This is a magical song, which has nothing to do with the usual subjects of songwriting (like, I don’t know, breakups) but feels just as intimate and personal as anything.
Hans Pucket lays it all out about modern life in a remarkably economical lyrics sheet, in a song that has all the epic scope of something like 10cc’s “I’m Not in Love,” and some of the hocketing harmonies even. It’s a song about love after a whole record about anxiety, which makes its sentiment feel earned (and maybe makes it less powerful as part of a playlist—go listen to the record!). It’s also one of the rare songs where I know viscerally what it means, but I couldn’t tell you in words! I’ll try anyway. I think it gets at the tension between wanting to not be complacent but also wanting to have a good life. In a way that is much more sophisticated and eloquent than that frankly embarrassing sentence.
A perfect pop song. Perfect!
This one crept on to my list this year. I just think it’s a beautiful song that does everything I’ve wanted to do lately as a songwriter. Dang! Well, I’m glad it exists.
There has to be something by Elliott here. I think this is probably the one I’d pick, if you held a gun to my head. What an insane scenario that would be. People do have strong feelings about Elliott, I guess, and I’m not above it, clearly! There are other songs I like better conceptually, but this might be the best one to actually put on and listen to.3
Jon Brion’s grunge-tinged, somehow also jazz-tinged epic about… not wanting to leave his room? Yeah. I can relate.
This gets a spot on my list purely for its outsized influence on my songwriting. I don’t know of an album that I listened to more, at a more critical age, than Sean Lennon’s Friendly Fire. Which basically explains everything about me, I think: I put this kind of Beatles-y melody writing above everything else, and I’m embarrassed to like the things I like. But now you know all about me. Oh well. Consider: the audacity of calling this song “Dead Meat” and then making a period music video about it where he dies in a swordfight. It’s just awesome, and it bypasses all my usual censors for being over the top/too on the nose. Matt Chamberlain on those drums… he’s good, isn’t he? He knows his rudiments, at any rate.
There you have it. Those are all the best songs. The only glaring omission I can think of is Richard Swift, but I just can’t settle on a single best song of his.
Next week, we’ll either do some new music or… compressors? I don’t know. What do you want to hear about?
I would never hold a negative musical opinion
I’ve stolen this joke from Guy Montgomery
Which is what counts! Never let them tell you that’s not what counts!