One week ago, Will Toledo had to rewrite a song to avoid breaking the law. It seems he had personally annoyed Ric Ocasek of The Cars, a brief cover of whose 1978 hit "Just What I Needed" used to bridge the gap between two tracks on Teens of Denial, the latest album from Toledo's project Car Seat Headrest, which is out online today. The sample was meant as a riff of sorts on the puzzlingly mundane name that Toledo has used for his music since 2010, when he was 17 and would record demos in the privacy of his parents' vehicle. "It was just a song I was listening to at the time,” Toledo tells me. "It was more or less a joke on my part: How far can we take it? How much of the song can we put into it?”

None, actually, owing to a communication breakdown somewhere in the sample-clearance process. But Toledo didn't mind: He completed a full rewrite of the song in 48 hours, just in time for Teens of Denial's digital release. The album's entire vinyl run had to be yanked from stores and physically destroyed, but hey, mistakes happen in rock and roll. (A repressed LP edition will arrive later this year.)

This wasn't even the first legally mandated edit Toledo had to make to Teens of Denial. Another song, “Unforgiving Girl,” originally contained part of a Neil Diamond composition, which had to be written out for similar reasons. Other references made it to the final product: Toledo sings part of Dido’s “White Flag” on “The Ballad of Costa Concordia,” changing the lyrics to be even more depressing and incoherent: “There will be no more flags above my door / I have lost, and always will be."

Copyright-law obstacles come up more often in hip-hop and house, where sampling is foundational to the genre, than in indie rock. But Car Seat Headrest was born online, where musical snippets flow freely from song to song, where the mash-up genre was born. He disseminated his early work through Bandcamp and Reddit, and his scratchy fever dreams are as much about listening to music as they are about making it. The rewritten version of what’s now called “Not What I Needed” bites one of Toledo’s own songs, “Something Soon,” from last year’s Teens of Style, his Matador Records debut after 11 self-released online albums. He’d planned on saving a reversed version of that song’s outro for a future album, but spliced it into "Not What I Needed" when he realized it was in the same key as the following track on Teens of Denial. "I like it better than the original version,” he says of the reworked song. "That was my least favorite song on the album already. It was the least emotionally engaging to me. It seemed kind of smug and sarcastic in a way that I didn't really want to pursue. This changed the tone of it and brought some more emotions to the surface."

Toledo overlaid the reversed section of “Something Soon” with a recording of himself explaining his band name to a German radio station, to preserve the joke originally wrapped up in the Cars sample. "The same day I was preparing the demo of the new version, I had to do this interview,” he says. "It wasn't a very good interview. It was hard to understand them, and they were not asking great questions, so afterwards I recorded it and then when I went back and listened to it I immediately thought I should stick this on the demo as well. It was a very of-the-moment thing."

For all the last-minute tinkering, Teens of Denial is a far more ambitious, fully realized record than the ones Toledo would put together in parking lots. It lays out his longtime fixations — depression, anxiety, drugs, alienation, God, Top 40 radio — on a grander stage than ever. He’s equally quick to reference a pop song from 15 years ago as he is the biblical tale of Sodom and Gomorrah: They're both part of his idiosyncratic vernacular.

Toledo started mining the Bible for material a few years ago, after he was required to take religion classes as an undergraduate at Virginia's College of William and Mary. He didn’t grow up especially religious, but he was fascinated by the storytelling potential of Christianity and the ways its mythology still informs the way many people cope with everyday suffering. “Pop culture works a lot like religion,” he says. Celebrities are canonized like saints, while songs can spread like prayers.

On “Drugs With Friends,” Jesus himself shows up to party-shame Toledo while he trips on psychedelics on his friend’s bedroom floor. On the record’s opening track, “Fill in the Blank,” God, the cops, and the audience all agree that Toledo should “stay the fuck down.” Police appear in his lyrics almost as often as deities, which makes sense given the power of both to surveil and kill at will. (According to the lyric sheet I received for the album, “Not What I Needed” was at one point titled "There Is a Policeman Inside All of Our Heads, He Must Be Destroyed.”) Toledo sings like a young person terrified of being watched, and also desirous of the same thing. Being watched at least means you exist. He name-searches his band on Twitter, and tells me that he reads his reviews.

Keeping tabs on what your listeners think of you is easier than ever in the Internet age, and Car Seat Headrest is very much an Internet band. Toledo’s songs often sound like they could have been written in the ‘70s, ‘80s, or ‘90s, until you catch a more modern word in the lyrics: “They've got a portrait by Van Gogh / On the Wikipedia page / For clinical depression / Yeah, it helps to describe it,” he sings on “Vincent.” He’s articulating a fairly new headspace: It wasn’t always possible to type keywords into an infinite database to try to figure out why you feel so much like shit, only to be greeted by the art of a man who suffered alone and died alone 125 years back. (As of writing, Van Gogh’s "Old Man in Sorrow (On the Threshold of Eternity)" is still the lead image on Wikipedia’s entry for major depressive disorder.)

There’s so much comedy in suffering if you’re able to look at it from the right angle, especially when you’ve got the echo chamber of the Internet to scream into. For Toledo, laughing at his own misery provides a kind of catharsis, and Teens of Denial is one of the funniest records about soul-crushing despair you’ll hear for a while. On the eight-minute breakup epic “Cosmic Hero,” Toledo sings with both middle fingers lifted high in the air: “I will go to heaven / You won’t go to heaven / I will go to heaven / I won’t see you there!” He gently mocks his own bad habits on “Drugs With Friends”: "Hangovers feel good when I know it’s the last one / Then I feel so good that I have another one."

"I look for humor as a way of balancing emotions in my own life,” Toledo says. "The TV shows or movies that I watch, they usually do the same thing. I prefer stuff that is a blend of comedy and drama or tragedy or whatever, stuff that doesn't limit itself to one emotional tone. Wes Anderson would be a good example of that: His comedic moments are always offset by dark moments, and vice versa. That's the model I'm working off of in writing my albums."

It helps that Toledo has a gilded ear for hooks and a yelp that sells the darkness in his songs as readily as it does the jokes. The album’s most tightly coiled song, “Destroyed by Hippie Powers,” broadcasts the full emotive range of his singing. He goes from delivering sullen one-liners (“It’s more than what you bargained for, but it’s a little less than what you paid for”) to cracking his voice in one of the record’s most intense and revelatory moments. “What happened to that chubby little kid / Who smiled so much and loved the Beach Boys?” Toledo asks. “What happened is I killed that fucker / And I took his name and I got new glasses."

Shedding former selves in your late teens and early twenties is painful, especially when those selves are preserved in music as if in amber. Toledo has quite the fossil record of who he used to be from the last six years of using Bandcamp, but Teens of Denial feels like a break from that history. Car Seat Headrest is a full band now, a touring act, no longer an isolated project. Toledo is 23, and keenly aware of the eyes that now fall on him. He’s ready to leave his teens behind.