#17, “Williamsburg Will Oldham Horror,” Jeffrey Lewis (2005)

150 Favorite Songs: #17, “Williamsburg Will Oldham Horror,” Jeffrey Lewis (2005)

The worst day of my life wasn’t really all that bad.

I don’t remember much about it, except for a two-hour stretch in the middle of the afternoon, where I had what I think might have been an actual panic attack. I was twenty-eight years old and living in London. Kat and I had a studio flat out in Zone 3, which is to say it was far from everything you think of when you think of London. The exchange rate was terrible that year, so our rent was $5,000 a month, which we were paying out of student loans. We’d been living there for almost a year at that point. It was a hard year.

Kat was in grad school and she was at class that day. I was home, which is where I often was because London is very expensive and we didn’t have much money. I spent a lot of time sending out query letters for a novel I had written about New Orleans. Most of those query letters resulted in either a form rejection or no response whatsoever. It was extremely disheartening—not that the book was getting rejected, which I was prepared for, but that my attempt to get someone to even read the book was getting me nowhere.

I was about ten years in to chasing big dreams for my life. I’d dropped out of college almost as soon as I started, having decided that I didn’t actually care if I learned any of the things they were teaching. I had signed up for five classes and dropped three of them within two weeks, or maybe I just stopped showing up. I don’t remember now. I lasted a few weeks longer with the other two, but I knew I wasn’t interested in being there any more than that. I wanted to be a writer. I wanted to write what I wanted to write, and I wanted to do it on my own terms. I stripped my life to the basics, kept my overhead low, kept my time my own as much as I could, and lived like that for most of the next decade. I didn’t like losing time to a minimum-wage job, which was all I was qualified for, so I started volunteering for pharmaceutical research studies to make a living, where you check yourself into a facility for a few weeks at a time, ingesting experimental drugs, and come out with a big check, the rest of your time your own. I really only wanted to do things one way.

I think, on some level, I also didn’t believe that the ways a person becomes a writer, like as a profession, were available to me. I grew up in Northwest Indiana, and then moved after high school to the Rio Grande Valley of South Texas. Neither of those are places that offer you a real model of what successfully pursuing an ambitious dream might look like. The most famous graduate from my high school has a Wikipedia page because he was the person who replaced Osama Bin Laden on the FBI’s Most Wanted list. If you come from certain places, it’s impossible to believe that your dreams could come true.

I assumed, for a long time, that the front door of whatever success I wanted would be closed to me, and so I was determined to go through the side. I wanted to be a writer and a performer and so I wrote on the internet for myself, for free, and I booked DIY tours as a performer, doing a mix of slam poetry and stand-up comedy that was ultimately, I think, pretty inaccessible to people who liked one but not the other and didn’t understand why someone would smoosh them together. I’m not even sure I had a good answer, except that it made sense to me.

By the time I got to London, though, I was tired. You, uh, do not make much money as a touring performance poet-slash-comedian performing in basements and community centers and punk rock clubs. There are transcendent nights and moments that make it all feel worthwhile, but I came to accept, after a few years of going full-bore in pursuit of it, that I wasn’t building something that was growing into what I wanted. I wasn’t going to be Bill Hicks or Saul Williams or Henry Rollins. When we got to London, I focused on finishing that book about New Orleans and then trying to get it published the traditional way. And I learned, quickly, that all of the things I had done that I thought were interesting and maybe even a little impressive—the venues I’d performed in and the experiences I’d had and the nights that felt magical, where I felt like I was at the top of my game creatively—they did not matter to anyone in the world I was trying to enter. I had spent so much time focusing on these things and they were the wrong fucking things. I couldn’t even get a literary agent to ask to see the first three chapters of the book to find out if it was any good.

And so that day when I was twenty-eight, sitting alone in that flat in London, I hit play on the song “Williamsburg Will Oldham Horror” by Jeffrey Lewis, and I don’t know if it triggered a panic attack or just soundtracked one, but all of the despair I felt about how little I had to show for ten years of work rose to the surface.

“Williamsburg Will Oldham Horror” is a frenetic folk song, built around a fiddle and a rapidly-plucked guitar and a neurotic sung-spoken performance from Lewis where he describes his own experience of chasing his dreams, and how pointless it all felt. And Jeffrey Lewis is someone who had accomplished more than I had at that point, was several tiers above the one I’d found myself on as a performer, was at a level that, I always thought, I would have felt pretty good about if I’d ever hit it. And I realized listening to the song that this was a trap—that there was no feeling of having made it. There was only ever likely to be more disappointment.

This wasn’t a deep insight from me; it’s right there in the text. The song is built around the conceit that he is on the train to Brooklyn and he sees someone who looks like Will Oldham, a folk-rock star who is several tiers above him on the ladder of success, in the same car, and from there, he starts unleashing his own neuroses. And he lays out these lines in a frantic, rapid-fire delivery, that felt like he was reading my mail. (It also ends in a weird, sorta rape joke, for some reason I don’t really understand, but which is nonetheless unfortunate.)

is it worth being an indie rock star or are you better off without it? he asks, explaining, cuz i mean maybe the world would be better if we were all just un-creative drones, no dead childhood dreams to haunt us, a decent job, a decent home. and if we have some extra time we could do real things to promote piece. become scientists or history teachers, or uncorrupt police at least. As the song continues to descend into that neurosis, he starts begging him for answers. you’re like the king of a certain genre but even you must want to quit, like if you hear a record by bob dylan or neil young or whatever, you must start thinking, ‘yeah, people like me, but i won’t be that good ever.’ and i’m sure the thing is probably dylan himself too stayed up some nights wishing he was as good as ginsberg or camus. and he was like, ‘dude, i’m such a faker, i’m just a clown who entertains, and these fools who pay for my crap, they just have pathetic, puny brains.’ and camus probably wished he was milton too, or whatever, you know what i’m saying?

And, well, shit. I spent two hours listening to this anxiety-inducing song on repeat that day, feeling an incredible amount of frustration about the direction I saw my life going, feeling like whether I knew it or not, I had peaked at twenty-four, and that peak wasn’t really all that high, and my future was to be the oldest person in every room, chasing a dream I didn’t know how to quit, till it was past the point where that feels noble and punk-rock and to the point where it’s deeply sad, but that the alternative was to go college, which I still didn’t want to do, or to just get a straight job and try to contort myself into someone who’d fit into it.

how long should an artist struggle before it isn’t worth the hassle? and admit that we aren’t fit to be the one inside the castle? is this quest for greatness or at least hipness just a scam and too much trouble? but then what makes one human being worthy of an easy ride, born to be a natural artist you love or hate but can’t deny, while us minions in our millions tumble into history’s chasm.

The way Jeffrey Lewis delivers these lines, in this song-song voice, fitting way too many syllables in each one and making up for it by speeding through them all double-time, it was how my brain felt—that day and maybe that whole year in London. I tried to shake myself out of whatever I was feeling by taking a shower and instead found myself coming up with verses that fit the melody about my own life, and stood there for I don’t know how long, really feeling the weight of a life that felt like it could never turn out the way I had hoped it would.

Eventually, I got out, and I did something normal, and another normal thing after that, and probably more after that, and eventually whatever despair I felt gave way to some other feeling at some point, and then I guess I went to bed and that day was over and on the next one I didn’t feel as bad as I had on that one.

There have been days where worse things have happened to me, of course. I’ve been hit by a car. I’ve had to cancel plans to fly to Indiana to watch my dad die of a sudden-onset illness. I’ve had days where I felt loss that made it seem like I couldn’t breathe. But that day was worse, because it felt like the future I wanted was foreclosed, like the entire tunnel of the future was narrowing and would never be anything other than narrow and dim, and I was suddenly being awakened to that fact.

But also: It is rare, as you get older, to find a song that so fully encompasses what you’re feeling, and if you relate to your own feelings in part through listening to songs, then having access to one that speaks to an uncommon experience that comes later in life is very meaningful. I wrote earlier here that I didn’t know if the song triggered or just accompanied the panic attack, but I also know that the feelings I felt that day had been there before I heard the song. The song just gave me access to them.

The next night, I wrote Jeffrey Lewis a kind of weird fan letter, telling him about this and about how the song made me feel terrible but then also better because it helped me clarify something that had been haunting me for a year in London. The letter is too long and too personal and it’s embarrassing to look at now, except that he wrote back a few hours later and said some things that made me feel a little bit better. I quoted this line before in this series, when writing about Sharon Van Etten and how she became the one of my group of house-show performers who became famous, but it meant a lot to me at the time when thinking about the point of doing things for myself, too. It’s a little bit silly, which helped me feel less embarrassed for pouring some things out to a stranger, too. “If it takes a million monkeys at a million typewriters to accidentally turn out something awesome and vital, then even the monkeys who never get recognized DID contribute to the process. All of us creative types are part of the big monkey machine. If there wasn't a million of us, nothing great would ever be created.  Which monkey's typewriter it comes out of, who knows, luck, whatever—we are all part of the process.”

I like that thought, because it gives an answer to the question of “why do this if it’s not working” that doesn’t feel like bullshit. You do it because the things we create add to a world full of creative things, and that is enough for it to really matter. Everything else is luck or timing or resources or being a nepo baby or whatever, and you can’t control any of it. You can just make things, and the world is better when people do that, and everything else is out of the rest of our hands.

And, look. Life is very strange, and it moves in ways we can’t conceive. We came back to the U.S. a few months after that day I spent listening to “Williamsburg Will Oldham Horror” on repeat and I came to accept that, if the things I had done in the years prior weren’t legitimate enough to get someone interested in reading my book, I would figure out what things would make me seem worth reading and do those. I decided I should try to get a few publication credits somewhere, so I could put those in a query letter that might get an agent to ask for pages. It turned out I was good at doing that, and within a year or two of trying, I was a full-time freelance writer. I taught myself enough reporting skills to call myself a journalist, and then I had a career as a writer, the one thing that seemed absolutely impossible that day in London. I still have it. I’ve had a book published. The one about New Orleans—it wasn’t ready then, either, just like I wasn’t, and I didn’t know that yet about myself or the book. Maybe some day it will be. If so, I reckon I ought to include Jeffrey Lewis in the dedication.