I recently found myself in one of those “What’s the strangest thing you did for entertainment during early quarantine?” conversations that somehow, almost half a decade later, people still aren’t sick of having. The usual suspects popped up — sourdough starters and Tiger King and whatnot. When it was my turn to respond to the icebreaker, I shared that during one week towards the end of April 2020, I listened to every Car Seat Headrest album in chronological order — from the esoteric, near-indecipherable sandpapery pop-rock of the numbered albums, all the way up to the 2018 reimagining of Will Toledo’s tangled teen angst rock opera, Twin Fantasy. All of it was in preparation for the group’s most recent and in some ways most confusing LP to date, Making A Door Less Open, which dropped just days after I finished my mission of lockdown-induced Car Seat Headrest completism.

Most fans are already familiar with Car Seat Headrest’s origin story: After fronting a few short-lived bands in his hometown of Leesburg, Virginia, high schooler William Barnes (now better known as Will Toledo) began recording original songs in his family’s 2000 Toyota Sienna because it was the only place he could do so in private, hence the moniker Car Seat Headrest. He uploaded the first couple records — titled 1, 2, 3, and 4, known colloquially as “the numbered albums” — to Bandcamp the summer after his high school graduation.

The online streaming platform was just three years old when Toledo started releasing Car Seat Headrest records. Bandcamp launched the same year Tumblr did, and by the mid-2010s, the two platforms would become enmeshed in a symbiosis that allowed independent music hosted on Bandcamp to proliferate on Tumblr, offering accompaniment to the blogging platform’s burgeoning online subcultural communities. The year the numbered albums dropped was the same year that Bandcamp first enabled cross-platform link sharing, an update that would prove instrumental to Bandcamp’s impact on the incoming indie rock boom. The second half of the decade would see Bandcamp becoming synonymous with a wave of artists who’d cut their teeth on the platform getting signed to legacy indie labels and garnering generational influence and acclaim. Its list of major success stories includes names like Alex G, Japanese Breakfast, Mitski, Mac DeMarco, and Car Seat Headrest.

Will Toledo has voiced his appreciation for how Bandcamp, especially during its earlier days, felt uniquely connected to “the flow of the internet,” its artist-curated interface a far cry from the depersonalized streaming glut of today’s online music landscape. When I would discover new music through Bandcamp and Tumblr as a high schooler in the 2010s, it felt like I was actually finding something, whether I was stumbling on it or actively seeking it out. It was a form of digital cratedigging that, by the time the early 2020s rolled around, already felt reminiscent of a bygone internet. Of course, Bandcamp still remains one of the best avenues for listeners to discover new music that probably wouldn’t make its way to them if they hadn’t sought it out. But the wave of the Bandcamp-breakout-to-indie-darling pipeline has long since crested, and the platform’s acquisition by Epic Games and later Songtradr (the latter of which resulted in mass layoffs of Bandcamp’s staff and a refusal to recognize their union) are telltale signs of the platform’s gradual subsumption into the corporate streaming landscape.

In the infancy of both Bandcamp’s internet presence and Car Seat Headrest’s career arc, the platform lent itself to Toledo’s penchant for re-sequencing albums and rearranging songs. The cylinders in my brain would start firing each time I recognized lyrical recurrences — the line about “pulling the out the nail with the back of a hammer” from “Bodys” that returns in “Beast Monster Thing (Love Isn’t Love Enough),” arc words “Art gets what it wants and art gets what it deserves” — or entire songs like “Big Jacket” and “Oh! Starving” that have multiple rewritten versions that appear across Toledo’s discography. You risk becoming way too invested in this affinity for revision upon listening to Toledo’s entire discography and — if memory serves correctly — nothing else for a full week while finishing up your senior thesis, quarantined with your family.

I entered into lockdown 21 years old and just months away from graduating college — an educational and developmental phase not all that unlike the one Toledo was in while writing How To Leave Town, his last album before signing to indie power player Matador Records, which turns 10 on Thursday. My own senior year of college was abruptly cut short. One Sunday in early March my school’s administration sent out an email telling students to be extra vigilant about washing our hands; by Friday, they sent out another telling us we had four days to pack up all of our belongings and evacuate. My friends and I said hurried goodbyes and scattered across the country, not knowing when we’d be able to see each other again.

I was back under my parents’ roof — where I’d end up living for the next two and a half years through varying levels of underemployment, uneasy stages of returning to normalcy, and a seemingly neverending postgrad malaise. I knew that, relatively speaking, I had it easy, but that wasn’t enough to keep me from feeling sorry for myself. (Toledo snarking, “Real life’s a mess/ But at least you’re not paying rent!” hit especially hard during this time.)

I went to class on Zoom and retained almost nothing. I struggled to get myself to find any purpose in my liberal arts degree as the hospitals were overflowing and bodies were piling up in the streets. When my mother asked if I was looking forward to graduation I couldn’t even bring myself to lie. What was there to look forward to other than a YouTube video ceremony (the slideshow of my graduating class made it look like we’d all died), followed by my entrance into a nonexistent job market, under a government that was willing to let its citizens flail through a time of global crisis with little to no institutional support. I was already racked with anxiety about my post-college life before I’d ever heard the word “coronavirus”; now, the “real world” I’d been both cowering from and preparing for was disappearing before my eyes (and everyone else’s), replaced by something unknown and sinister.

I’m not sure what specifically made me decide to do a Car Seat Headrest discog deep-dive in quarantine, other than my desire to brush up before the band released their first album of entirely new material since their 2016 breakout, Teens Of Denial. The one-two punch of Teens Of Denial and its rhyming predecessor, 2015 Matador Records debut Teens Of Style, elevated Car Seat Headrest from internet esoterica to indie rock household name. Made up almost entirely of re-recordings from Toledo’s pre-2013 material, featuring some updated lyrics and a full band, Teens Of Style served as a sampler of Car Seat Headrest’s already-prolific output packaged into a gateway compilation for new fans.

As a songwriter, Toledo has always trended toward self-referentiality, often sampling, interpolating, or in other ways alluding to parts of older songs in new ones. Recurring phrases, images, characters, and leitmotifs pop up throughout his discography, and he’s not afraid to get metatextual. On the original recording of “Times To Die” from 2012’s Monomania, Toledo sings about “Worming my way into your heart/ Worming my way onto the charts” and making a deal with “the divine council” in a refrain that juxtaposes Biblical allegory with his own struggles to make it as a musician.

In addition to featuring more hi-fi production and additional instrumentation and backup vocals, the song’s Teens Of Style update has Toledo shouting out Matador Records founder Chris Lombardi in one of the verses — “Got to have faith in the one above me/ Got to believe that Lombardi loves me” — and replacing the line “no unsolicited demos” with “Hey man we listened to your demos.” The original lyric is a sample from a 2009 song by Will’s high school band Nervous Young Men, unsubtly titled “Fuck Merge Records.” While the lyric change on their Matador debut was an intentional and obvious reflection of Car Seat Headrest’s matriculation from unsigned one-man band to indie rock major-league player, many of the lyrics on their final non-label record were ones that questioned whether Car Seat Headrest was ready for its impending level-up.

How To Leave Town shows Toledo’s referential tendencies at their knottiest and most self-interrogating. “I cowrite my songs with myself/ He feels the feelings, I write the words,” Toledo sings on “Beast Monster Thing.” Later on the record, he amps up the stratification between himself and his artistic persona on “I Want You To Know That I’m Awake/I Hope That You’re Asleep,” a bitter breakup song about the dissolution of a relationship and a creative breakdown. He overdubs his vocal harmonies, sonically and metaphorically keeping himself at a distance as he offers, “Here’s the demo of my latest sentence/ I’ll fill in the good parts later.”

During the song’s bridge, he rattles off a list of the endings of various romantic and creative partnerships — Mike Love and Brian Wilson, Frank Sinatra and Ava Gardner, the Beatles, a couple of Toledo’s friends, “my parents and your parents” — capping off each entry in the list with the reassurance “But we’re not like them/ No, we’re nothing like them.” It all goes to highlight the muddied lines between personal life and creative life, what happens when the story you tell yourself refuses to be confined to the page or the record. Additionally, it can be a fun/stupid activity to use Toledo’s formula of “[x couple] broke up today/ But we’re not like them/ No, we’re nothing like them,” swapping out the lyrics for names of people you know who’ve gone through breakups recently (behind their backs, obviously).

Much of How To Leave Town is Toledo questioning how much of themselves an artist is supposed to give away: Where does the artist end and the human being begin? Does writing one’s own life stories into a record consecrate or desecrate them? What are your emotions and experiences worth? What about the emotions and experiences of the people you’re writing about? What stays sacred?

Toledo had amassed his modest cult following with songs that were deeply personal, all of it coming to a head with the crushingly raw account of his first love and first breakup on 2011’s Twin Fantasy, considered then and now to be his magnum opus by many diehard fans. In 2014, Toledo was on the cusp of opening himself and his music up to a much bigger audience (though how much bigger he couldn’t quite anticipate at the time). The question of how much personal/professional separation to afford himself loomed large, probably larger than he knew.

Toledo did not know for sure that How To Leave Town would be his last non-label album while he was writing it, but somehow it became a swan song to his Bandcamp era, littered with little goodbyes to his time as a pseudo-solo artist and moments that would predict the shapes his career would take in the following years. His “Hey! Can you hear me now? Am I alone in my futile effort?” shout into the void on “The Ending Of Dramamine” would be answered in an indirect yet literal sense less than a year later by the folks at Matador. The rollicking chase for Toledo’s own version of the American Dream on “America (Never Been)” would make the song retroactively come off his bachelor party before being wed to a three-album record deal and a band that was more permanent than a rotating cast of session players.

Toledo didn’t even think of How To Leave Town as an album at all; he insisted, in All Delighted People fashion, on calling an hour-plus collection of songs an EP. But this paean to heartbreak, artistic identity, and existential angst — as well as Toledo’s flirtations with electronic arrangements and sprawling post-rock — still feels as narratively and sonically rich as Car Seat Headrest’s more lauded conceptual works like Teens Of Denial and Twin Fantasy.

How To Leave Town is a road trip album, a genre staple unsurprising to anyone familiar with Will Toledo’s lifelong study of rock history and borderline-neurotic fixation on his own place in it. This record engages with that history directly, often through the dissection of the pedestals that Toledo’s heroes stand on. On “Kimochi Warui (When? When? When? When?),” the deconstruction of Toledo’s idol worship is rooted in a reference to a Brian Wilson biography that he read (likely Peter Ames Carlin’s Catch A Wave): “His father never loved him/ And the band just wanted the money/ And Dennis was an alcoholic/ Who drowned looking for treasure.” The slow-building 11-minute closing track, “Hey Space Cadet,” has Toledo alluding to the talent and tragedy of legends from Elvis Presley to Daniel Johnston while driving through their hometowns and final resting places.

“You could drive across the whole thing in four days if you really wanted,” Toledo sings on “America (Never Been).” It’s the most obvious nod to the record’s road trip concept, its place at the near-halfway point in the tracklist coinciding with the geographic “middle” of the continental US. While introducing the song during Car Seat Headrest’s first KEXP performance, Toledo, dressed like he stopped by the KEXP studio on his way to a shift waiting tables at Olive Garden, deadpans, “This song is dedicated to my haters, because what is a man without his haters?”

Toledo’s getaway is not the fist-pumping, screw-this-town-let’s-ride-off-into-the-sunset Springsteenesque saga that the Great American Road Trip Record usually connotes. It’s marked by icy electronic passages, faraway feedback, and lo-fi spaciousness that evokes the creeping emptiness of American expanse. The uncanny teeny-bopper power-pop melody of “You’re In Love With Me” bounces around in eerie, extended instrumental passages and its seemingly-sweet chorus — “You could be in love with anyone/ But you’re not in love with anyone/ Because you’re in love with me!” — warrants a double-take. The “with me!” repeats in a fuzzed-out echo for an uncomfortably long outro, like a talking doll with a broken string, or the spotty connection of a radio station barely accessible on a deserted stretch of highway.

While road songs tend to present the life of a traveling musician as either a lawless, hedonistic thrill ride or a lonely existence apart from loved ones, How To Leave Town treats it with the same drudgery of any other job — perhaps because it’s not really about touring at all. Toledo’s travel diary is dogeared with references to the mundane and the bureaucratic inserted into surreal scenarios — a gas station providing shelter from an ice storm becomes a “frozen oasis,” heaven has a zip code and P.O. box number (Will Toledo’s actual mailing address at the time of the album’s release), Toledo’s retelling of a dream about Barack Obama coming to his birthday party includes a quip about how his friends “made a giant banner of my face/ I wish they hadn’t used my driver’s license photo.”

The haunting opening track, “The Ending Of Dramamine,” sees Toledo at a deserted rest stop in Montana. Its title is an in-joke about Modest Mouse and how the ominous reverbed guitar sounds at the outro of their debut album opener really creeped out Toledo’s friend Degnan Smith (of the band Naked Days). “The Ending Of Dramamine” clocks in at just over 14 minutes. The first five minutes are a slow-building drone solo, which returns and unravels for the last three, rivaling the discordance of its namesake before hitting the brakes. One of the track’s refrains plays in reverse — a line written tragically too late to be used as an angsty AIM away message but still perfect for tagging venue bathroom stalls: Thanks for fucking with my head, come again soon!

Toledo’s angst on How To Leave Town is both melodramatic and painfully lived-in, his bitterness palpable as he mutters “love is bullshit” at the beginning of “I Want You To Know That I’m Awake” and later in the song asks, “Mind if I cough in your ear all night? Mind if I resent you for a year tonight?” The Morrisey-like fatalism with which he sighs, “I have no faith in life to keep me satisfied/ I’ll have these doubts and worries until the day I die,” on “Kimochi Warui” is easy to roll your eyes at and just as easy to let rattle around your head, collapsing under the weight of the realization that being yourself is a life sentence.

Later in the same track, Toledo sings “Some of these things are symptoms/ And some of these are being human.” When you’re at the crossroads of young adulthood, getting tangled up in your own immaturity while trying to shed it, it can be impossible to differentiate the two. It’s like Toledo himself said two years earlier on his song “Souls”: “Did you cry because it was over? Or did you cry because it will never end?” Or, as the famous Samuel Beckett quote goes, “You’re on earth, there’s no cure for that.”

Throughout the summer and into autumn of 2020, I got into the habit of sneaking out of the house after my family members had gone to sleep — any thrill of sneaking out dashed by the dismal state of “outside” and the fact that I was 21 years old. I didn’t go anywhere, just sat on the stoop or maybe walked around the block, basking in what little enjoyment I could pull from just being allowed to exist in public, no one around to potentially infect or be infected by. Many of these nights were accompanied by How To Leave Town — closing track “Hey Space Cadet” in particular. I’d stare up at the two or three stars that were visible through the light pollution in the city, my head tilted as far back as possible. If I trained my eyes hard enough, the sky would surround me, and for a couple seconds, it would be all I’d see. I wanted to float through it.

“It is 2014 and I have no idea what is going on in my life!” Will Toledo howls at the beginning of “Hey Space Cadet,” before screeching distortion cuts in, followed by a thunderous wall of sound and Toledo’s crushed, voice-cracking approximation of a “Great Gig In The Sky” wail. He may not have had any idea what was going on in his life, but with each year that passes, the final track on his last pre-Matador album feels more and more like psychic manifestation.

By the time 2020 arrived and the now four-piece Car Seat Headrest rolled out Making A Door Less Open — a polarizing and doomed-by-timing record whose promotional cycle included Will Toledo donning a gas mask and assuming the role of a anthropomorphic rabbit alter-ego named Trait — How To Leave Town’s electronic, often loop-based songs seemed less leftfield in the context of Car Seat Headrest’s growing discography. If anything, it had proved to be a prophetic sonic turn.

“Hey, Space Cadet/ It’s time to show them what you can do,” Toledo pleads toward the song and the record’s end, “What can you do, man? What can you do?” His existential question doubles as a here-goes-everything hype-up to prove himself that this whole music career thing is really worth taking a chance on. All the dreaming, all the “dancing in my mind,” somehow found its way into reality. He had to wait a little while for his transmission to echo, but in the decade since he first sent it off, a chorus of far-off voices that he didn’t know he was summoning have answered back. The Space Cadet sings; down here on earth, we’re still listening.