I remember two stories people have told me about Tom Waits.

The first one is this: When my friend Joe was in high school he would give his younger brother, who was ten at the time, rides to school. For whatever mildly sadistic reason, Joe would proceed to lock the car windows and play select tracks from Bone Machine (the Waits album that sounds like a psychedelic nightmare-carnival) at maximum volume until his brother started crying.

Next is something from my friend Jon. I don't remember the song, but he would play the same one, all the time. I think it was from Rain Dogs, but it doesn't really matter. What matters is how afterward, he would tell me about how his dad disliked music, almost all music, but whenever he heard that one specific Tom Waits song, he would stop whatever he was doing and ask Jon to play it again.

Here's my point: people like Tom Waits for a lot of reasons. It might be safe to say they hate him for just as many. I think my response to his music is probably just as minuscule and idiosyncratic as everyone else's. From Mule Variations (the album The RS 500 has paid me handsomely to write about), I'm thinking mostly of the song “House Where Nobody Lives.” In other albums there are many of his songs like this: “Kentucky Avenue,” “Christmas Card from a Hooker in Minneapolis.” They’re songs that seem to be longing for a place that meant something to Waits, but a place that's now long gone.

And for a lot of my life I've been overwhelmed by places. Maybe more than most people, I don't actually know. What I do know is that trying to convey what's meaningful to me about them is overwhelmingly difficult. I've been writing for a lot of my life too, and I'm finally at peace with the fact that I won't ever be able to communicate, or communicate fully, what a place means to me. Before you stop reading because you've already read Derrida or Jacques Lacan, hear me out. What I want to tell you is why I think we can't write about places, and what any of this matters for. If at all.

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I think a lot about buildings, and how beautiful and weird and sad they can be.

I think a lot about Pizza Huts, and how they amaze me. I'm not talking about the food (except for the lunch buffet: always relevant), but about the actual structures they're in. As a kid growing up in the 90s, I loved the restaurant, and would get excited by that bizarre trapezoidal edifice whenever I saw it.

But something weird happens to me now. I'll often drive by someplace that was built to be a Pizza Hut, but then re-purposed for another storefront. Even then, even though a pizza may not have been cooked inside that structure for a full decade, I recognize it. I love this, how the shape of a building alone can recall something meaningful, how arbitrary designs are coded into our psyches, and become activated by the strangest things, in the strangest ways.

And what else I love is that it's these shitty, overlooked buildings that actually become the stuff of our lives. We often want to define places by landmarks: the Eiffel Tower, the Empire State Building, something Frank Lloyd Wright built, etc. Famous buildings or architectural anomalies are cool, sure, but they're novelties. I grew up just outside of Chicago, and what makes me think of the city isn't the Sears Tower, but the piss-smelling L train and an under-lit, smokey basement off 26th Street. We live and create through vernacular architecture:

Suburban ranch homes lined up quietly in the summer dark.

Driving through Indiana, you can see for miles. When it's warm out, everything on blacktop shimmers and it makes me sad for some reason I cannot explain.

Once I walked alone to a gas station at 4 o'clock in the morning to buy candy. I was 16. It was winter, and it was so bright from the snow reflecting moonlight I could see like it was day.

And if our lives are determined by the finite, imperfect spaces we live in, then, too, are our memories. Geography informs memory more than anything else, I believe. And for Waits and myself, place is enormously important in a specific type of remembering: nostalgia. So many of his songs, the ones I like most, are about this (especially “House Where Nobody Lives”): the desire to communicate a place long gone to him, and because of this, someplace longed for.

There's something about nostalgia that makes places and things more wonderful and more painful. It's a lens we see through, but any light from the past that's visible has already been refracted. Nostalgia is, if nothing else, a distortion. It makes us yearn to communicate things even more, yet it makes it harder to communicate anything accurately.

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I might be crazy, or stuck in my own head (or both!), but I think Tom Waits understands all of the consuming, unnameable drive to communicate something about the places and landscapes that define our lives.

What he also understands is something I do too, finally: the futility of all this. For me, all of his twisting and turning through personas, atmospheres, and different interpretations of familiar landscapes, is the attempt to convey at least something about the places that matter to him, while recognizing the impossibility of doing so completely. Maybe only from a hundred separate perspectives can we begin to convey a place essentially. But maybe, probably, we can't, yet will still try just as hard. Just as hopelessly. And there's something great about that too.

I'm not saying this is what Tom Waits is all about. I'm just saying I think it's present: present in Mule Variations, in Bone Machine, in Rain Dogs, in whatever. It matters to him. And it matters to me. And it might matter to you, too, if you care about places, if you care about, say, the Monongahela National Forest, or your Uncle's cabin in South Dakota, or the shitty ranch house you grew up in. Even if it looks exactly like all the other shitty ranch houses around it. Even if you don't live there anymore; even if it's a place where nobody lives.

—Jack McLaughlin