“Teens of Style” is an introduction to Will Toledo’s back catalogue. Photograph by Ian Allen for The New Yorker

When Will Toledo was in high school, he read an article about a New York indie band that was commanding the attention of the music industry. It seemed as if all the group had done was upload its songs to Bandcamp, a largely unregulated online store where people can sell their music and merchandise at any price. Inspired, Toledo began parking his family’s car in different places in his home town, Leesburg, Virginia, and recording songs on a laptop in the back seat, his only audience being the car’s headrests. In 2010, he uploaded a collection of these wobbly, fairly traditional pop songs under the name Nervous Young Men, told people at his high school about his music, and waited. It didn’t take long for him to realize that his plan was not going to get him a record deal. But this reality proved to be liberating. He began to experiment with longer, stranger, more intimate songs, incorporating squiggly electronics and psychedelic squalls, and, after renaming himself Car Seat Headrest, began releasing a succession of albums on Bandcamp. Last year, at the age of twenty-two, Toledo released his eleventh album, which can be streamed for free on the site.

The major online music providers, like iTunes and Pandora, attract the most listeners, because their inventories are virtually limitless and grow by the day. But these giants also succeed by imposing a gentle hierarchy on their vast libraries, offering friendly curatorial touches that ease users deeper and deeper into this digital infinitude. In contrast, Bandcamp is a charming alternative, largely bereft of editorial guidance or heavy-handed gatekeeping. Browsing Bandcamp can feel thrilling or frustrating, depending on how much time you have on your hands. It’s a music store that thrives on randomness—I’ve recently found some of my favorite new artists by peering at the wishlists of other users, including some of my former students at the college where I teach. Earlier this year, Bandcamp announced that, through the site, fans had given its artists more than a hundred million dollars. But individual success stories are fairly modest. (They include the bedroom-pop musician Alex G, whose breakout album was released earlier this month.)

There are probably more efficient ways to find fans. But the site has allowed Toledo to work unencumbered by expectation, hidden in plain sight. The Internet is often considered a distressingly permanent space, where one’s youthful mistakes are preserved forever, but it can also be transparent and emboldening, hospitable to a casual, low-risk approach that allows an artist to explore and edit his personality, and to be prolific in the process. The rapper Lil B, for instance, owes his cult fame to the hundreds of earnest, contemplative songs he released on multiple MySpace pages.

In the twelve hours of Car Seat Headrest music available on Bandcamp, a world of Toledo’s making slowly comes into focus, that of an oldies-obsessed pop prodigy perfecting his Beatles and Beach Boys melodies, mostly playing all the instruments himself. Friendships and ambitions bloom from album to album. Parental relations improve. Riffs and choruses are revisited and reworked with new language to reflect changing times. Anxieties, particularly the pains and miscues of sexual self-discovery, rise to the surface, moving from subtext to song title. It’s like following a character through a series of inward, angsty novels, as if Elena Ferrante’s formative environment had been suburban parking lots, dorm rooms, and the Potomac River. On “You Have to Go to College,” one of his first songs, Toledo runs through a series of classic high-school preoccupations, from losing touch with friends to what it means to grow up and become a “decent human being.” Now we are entering the mid-twenties chapter of Toledo’s story, marked by a different calibre of worry.

For instance: his career. This week, Toledo and his newly assembled band will release “Teens of Style,” on Matador Records. Intended as an introduction to Toledo’s daunting back catalogue, it features new, self-recorded versions of his old material. Next year, he will release “Teens of Denial,” his first proper studio album. When Car Seat Headrest began, Toledo was drawn to outsider musicians such as Jandek, the once reclusive experimental folk-and-blues artist, who has self-released more than sixty albums. As Toledo explained to me, he saw himself as making music “for the Internet,” where his songs could exist free of backstory, without reference to time, place, or persona. He was scattering treasures to be discovered by chance. But, after he uploaded his first four albums, he began to receive attention from blogs and message boards, and decided that reclusiveness no longer suited him.

The original versions of the songs on “Teens of Style,” all of which can be found on Car Seat Headrest’s Bandcamp page, borrow heavily from nineties indie rock, with Toledo’s blissfully slack vocals resting on top of frizzy, grungy textures. They are the kinds of perfect, instantly familiar pop songs that echo in the background of your dreams. Over time, Toledo’s technique has become more refined. He spends less time hiding behind reverb. Good hooks have grown into full-fledged songs. He’s begun shading in more of his own identity. In the new version of “Times to Die,” he adds a line about Chris Lombardi, the Matador executive who first circulated Toledo’s music to his co-workers: “Got to have faith in the one above me / Got to believe that Lombardi loves me.” On “Beach Life-in-Death,” a twelve-minute song on the excellent “Twin Fantasy,” from 2011, he thinks back to the songs he wrote for a failed love: “I wrote ‘Beach Death’ when I thought you were taken / I wrote ‘Beach Funeral’ when I knew you were taken,” he laments, referring to songs from “3,” released the previous year.

The most arresting moments in Toledo’s music occur when a pop song begins to feel tragic and insufficient for real life. Writing songs may stave off boredom, but some voids remain. It’s an appealing irony that runs through Toledo’s albums: he can write songs so well formed, with such a divine lilt and of such sturdy beauty, while flailing at the words that might make someone fall in love with him. He’s confident enough to casually scat “Shabba de bop bop be shibby day oh yeah” but too shy to say it cleanly. “I pretended I was drunk when I came out to my friends,” he confesses, on “Beach Life-in-Death,” before admitting, “I never came out to my friends / We were all on Skype / And I laughed and changed the subject.” A pop song can take you higher, but it can’t take you out of Leesburg fast enough.

One of Toledo’s gestures toward self-promotion has been a Tumblr he has maintained during much of Car Seat Headrest’s existence. It features his latest press, responses to fans’ questions, photographs of his friends and himself, and brief entries about recently discovered bands. In this context, his songs begin to reveal themselves as a way of revisiting and revising everyday life. His fans are drawn into his world, too, using his Tumblr to wish him well and send him fan art, or ask him for guitar tablature, lyrical exegesis, and music recommendations. They thank him for being an inspiration. Mostly, they beg him to play more all-ages shows.

Toledo’s career thus far is a modern, indoorsy version of what it means to be young, testing your limits and pursuing ambitions in public, leaving the rough-draft version of yourself available for all to see. At its core is a sense of discovery, especially when it comes to the entrancing, soul-saving effects of other people’s music. His lyrics are studded with references to musicians he loved or copied, bands and artists he grew out of—Wolf Parade, Xiu Xiu, Brian Wilson, Leonard Cohen. On “Strangers,” from “Teens of Style,” he sings of his affection for R.E.M.: “Car Seat’s nervous and the lights are bright / When I was a kid I fell in love with Michael Stipe / I took lyrics out of context and thought / ‘He must be speaking to me.’ ”

Now Toledo is the one who is speaking. When you think you’ve heard it all before, you hear a melody that bends just the right way. He moves without the anxiety that it’s all been done before. Rather, there’s a confidence that it can be done again—better, catchier, more perfect, more honest. ♦