Car Seat Confessions: A How to Leave Town 12 Year Anniversary Retrospective

Every Sunday, milk crate revisits an iconic piece of music history—artist, album, or otherwise—as a part of our weekly crate digging series.

Design by Sophie Parrish

By Declan Ireland

How to Leave Town arrived at something of an awkward position in the history of Toledo’s discography. Released in October 2014, then followed swiftly by an unforgettable series of four years and three records: Teens of Style in 2015, Teens of Denial in 2016, and the Twin Fantasy (Face to Face) rework in early 2018. Yes, it seems to be a sad truth that How to Leave Town would be cursed from the start to a fate of quiet obscurity trapped in the shadow of its celebrated siblings. Especially when compared to the high quality production and somewhat conventional structure of a record like Teens of Denial, How to Leave Town seems like nothing but a misstep: a brief stumbling point in a long and successful career when, in reality, it is a transcendent experience in its own right, at least on par with if not possibly surpassing Toledo’s later work.

How To Leave Town is a lonely drive down a darkened highway deep into the pits of night. Its production is unnatural, robotic, like an early draft of an FL Studio project that never really finds a way to escape the uncanny valley. It is often disturbing and always at least disquieting, the whole album carried out in this uncomfortable, off-kilter kind of mode which never fully allows the reader to find their footing. Just on the edges of the fluorescent glow of the stilted drum beats and canned chord organ the black night stretches on and on and on.

While the record appears to be from a completely different planet when compared to some of Toledo’s more popular works, in truth it is but one in a long line of released and unreleased works from Toledo’s earlier years working in the same mode. The unreleased number albums (aptly titled 1, 2, 3, and 4 respectively), Nervous Young Man (2013), My Back is Killing Me Baby (2011), and Monomania (2012), when listened to in sequence, paint How to Leave Town in a far more flattering light. The record is not some antithetical piece of failed experimentation—awkward, adolescent, almost obscene—but rather, a culmination of a long project exploring a submission to the loneliness which Toledo battles so avidly in his later works. When taken as a group, cut off at the enormous success and overwhelming influence his later albums, it seems as if before the boom Toledo was a different artist altogether, one which labored not within the craft of angsty guitars and pubescent wailings, but rather, in a quiet, strangely mature misery both characterized by and burgeoned with by the alienated quality of his early music.

It is by now more than an open secret that Toledo despised his own music in the early years: he hated it while he was writing it, and it is not difficult to believe that he may still hate it now, especially considering the prog-rocky, almost operatic turn his outfit has taken in recent years. Thus his musical adolescence was a largely solitary experience. Most of his early works make heavy use of music production programs and drum machines as opposed to “the real thing,” in all likelihood because Toledo may not have had the guts to present it to potentially dissenting musical peers. The softer whispered quality of his vocals on these records is as much an artistic conceit as it is a response to constraint. They were recorded in his car as Toledo hid what he thought were fruitless and frankly embarrassing labors from his college roommates: shame is not just a motif in his music. For a long time it was an essential part of his artistic process, perhaps even his life.

This is the framework through which How to Leave Town may be viewed best. More than any other record in Toledo’s catalog it is a gift; a vulnerable secret shared between artist and listener alone.

The fruits of this artistry in confidence will reveal themselves almost instantly. How to Leave Town is simply a gorgeous, gorgeous album. The music production and lyricism stirs me in a way that I have found no equal to so far. There is no question about the fact that Will Toledo has always rivaled the likes of LCD Soundsystem in the mastery of the slow build to transcendent climax. Tracks like “The Ending of Dramamine,” “America (Never Been),” and, “I Want You to Know That I’m Awake/i Hope That You’re Asleep,” are the perfect holotypes of this talent. Each begins with some simple motif: wailing synths on Dramamine, echoey acoustic on America or scratchy electric on I Want You to Know That I’m Awake. The motif is then dug firmly into the listeners mind through endless repetition, almost ad nauseam. Yet, slowly but surely, the tracks change. As the minutes flow by almost painfully, new instruments slowly introduce themselves as Toledo’s lyrics grow more resonant and complex, eventually culminating in a torrential downpour of emotion and experience before the music slowly recedes to make space for the next track and prepare another barrage of feeling again.

This all not in the least to say the record is in agreement with itself. At times the listener wonders if it can even be considered cogent. “Kimochi Warui,” a tragic meditation on when self-help gives way to self-hatred (and my #1 track of 2024, regrettably) is followed by “I-94 W (832 Mi)” a voiceless, atmospheric track just barely scant of a minute and thirty seconds long, an odd include within the context of a record with a superficially small track number (only nine, though as anybody who has listened to the record will tell you, these nine go loooooong) which is then itself followed by “You’re in Love with Me,” the most bizarre track when compared with the whole: an almost disconcertingly chipper exultation of “good love” with lyrics more reminiscent of a slightly more verbose 1 Trait Danger track than anything else (1 Trait Danger being Will Toledo and Car Seat Headrest drummer Andrew Katz’s oft overlooked absurd comedy/faux-hip hop side project. More than a worthwhile project to explore at the very least to see what the artists’ inflections look like when they are not wallowing in abject misery.) All tracks which when looked at individually seem to clash aggressively with each other, or at the very least make no sense. My gut is telling me to insert some vague aphorism here about the complexity of the human condition and its relation to suffering but my gut is usually wrong and in all honestly it is never really that serious so I will abstain (perhaps just as Toledo might).

The record concludes with an odd sort of time capsule of a track. “Hey Space Cadet (Beast Monster Thing in Space)” appears superfluously as a letter from 2014 Toledo to some tragic, wavering portrait of an even younger self. As many 20-21 year olds often might claim, Toledo seems to insist upon knowing all the answers and possessing an intimate knowledge of what he needed at an earlier step and what he needs now;“Hey, space cadet /You’re gonna need a lot of love, but not the kind you’re thinking of.” And yet, the track may never sit comfortably in this certainty. Everywhere and always in this track and this album and all of Toledo’s discography beyond each admonishment or adoration which may at first glance seem absolutely certain carries a silent question mark on its back, a lingering uncertainty prompted not only by the lyrics themselves but as well by the general condition of Toledo’s work as a whole. The question is simple: Why? Or perhaps even simpler, how? How has Toledo somehow achieved this epiphany, this enormous truth at this precise moment following the inevitable floundering and self-conscious wallowing that comes with a Car Seat Headrest album? It reads to me as an individual found at the deepest point of a spiral who, in their enormous (or seemingly enormous) misery stumbled upon a similarly enormous fact about life, and yet, the spiral continues, or is escaped only to prompt a new one beginning again.

In its final moments, just as in the final moments of every Car Seat Headrest album, the record undermines itself. In my mind an amusing and largely spot-on portrayal of not just the artistic process but of the human condition as a whole (that whole promise about the no obnoxious aphorisms I really tried to keep, but sorry, I just can’t resist.) Toledo’s discography as well as the discography of any authentic artist (authentic meant here not in the vague “good music/bad music” sense, but rather, the ability of an artist to present themselves on the page or the track or the screen genuinely, even when it is unflattering) may very easily be read as the blueprint of a life. You struggle, you work, you slave. You hurt the people you love the most and prostrate yourself before them and sometimes you are forgiven and sometimes you are not. Something ends, something begins, and everything is different but over time you find the same problems emerging. It has often been said the life of an artist revolves around a sometimes singular, sometimes modal obsession. This is a conception I have tried my hardest to reject and bite back against but the more I work the more I find it to be painfully true. The life of an artist is this way because the life of a person is this way. Bad habits (in Toledo’s case, the idolization of a lover to an obsessive, almost spiritual degree) are hard to break , and never (and I mean never) are the seeds of those patterns really gone. It requires constant vigilance. And when the shield slips, the chink in the armor is located, that is when you must start all over again: rethink everything, rebuild your life from the ground up. It’s the reason why artists like Will Toledo, Taylor Swift, MJ Lenderman, and the like always seem to have something to complain about, and most frequently something eerily similar to exactly what they tackled and apparently moved past in the previously produced project. That is not to say the forms the obsessions take do not change, in fact, they often do drastically. The core experience which is sedated and lonely on How to Leave Town is made raucous on Teens of Style (2015) and then transformed into something angry and energetic to the point of paroxysm on an album like Teens of Denial. And on, and on, and on. and THAT is how the sausage gets made. How art gets made. 

All my Substack ramblings aside, you should really listen to How to Leave Town. It is a gorgeous, gorgeous album and simply does not receive as much love as it deserves, especially when compared to its younger and older siblings. Furthermore it is a perfect gateway into Toledo’s earlier works. I truly implore you to give it a shot. Take a long walk on a late cold night (as the nights get longer, and the cold gets colder I’m sure this won’t be hard to come by) or, if the opportunity arises, a long ride on a car or bus or even a train and turn this album on and feel what I have felt, what so many (and yet still not enough) have experienced and hopefully you will see what I see in this black sheep of the Car Seat Headrest Family. I promise you won’t regret it.