The best place to listen to music is on a train. Specifically in a window seat, passing by snippets of landscape and humanity frozen in random, occasionally embarrassing snapshots: Google Earth minus the bird’s-eye view. I covet the window seat, but I failed to secure it one morning this week, on an Amtrak ride only a little bit longer than the runtime of Father John Misty’s nearly-80-minute new album, Pure Comedy. This turned out to be a boon: Pure Comedy is one of the only albums I can think of that is better appreciated from an aisle seat, preferably in the back of a train car, with the other passengers’ erratic behaviors and glowing screens in full, voyeuristic view. As our train barreled forth, I watched one guy look up some golf courses on Google Maps; another turned his phone sideways and watched a violent TV show I couldn’t place. A man sitting on the aisle two rows up scrolled endlessly through his News Feed before stopping, for a good 30 seconds, to appreciate an Evil Kermit meme. “When the historians find us we’ll be in our homes … skin and bones,” Misty sings at the end of a song called “Total Entertainment Forever.” “A frozen smile on every face, as the story’s replayed: This must have been a wonderful place.”

Father John Misty — b. 1981, née Josh Tillman — narrates much of his new album with a sense of wry, zoomed-out remove, as though he were that historian, or perhaps the proverbial alien crash-landed on earth, trying to figure out why we have things like presidents and scissors and Facebook and lava lamps. He arrives here in the first track, “Pure Comedy,” a showy, gorgeous, six-minute piano ballad that sounds like Harry Nilsson trying (and somehow succeeding) to write a national anthem for the entire human race. It’s a lovely song. “The comedy of man starts like this,” Misty croons, “our brains are way too big for our mother’s hips.” This is an impossibly grand beginning, and yet it is not false advertising for the damn-near hour and a half to come. Pure Comedy is no less than — in Misty’s own words, which are often an indistinguishable swirl of braggadocious irony and self-deprecating sincerity — “a record about capital-H Humanity.”

Father John Misty’s origin story has been so widely reported at this point that we can here condense it down to its most compelling biopic beats. He grew up in a staunch evangelical household in Maryland, sheltered from most secular culture but in possession of a drum kit; at 18, he left home and also heard the Beatles for the first time. A stroke of luck got him a gig drumming for the po-faced folk-rock band Fleet Foxes in 2008, which more than paid the bills while he made earnest, self-described “sad bastard” solo albums on the side, under the name J. Tillman. Then, shortly after he quit Fleet Foxes in a fit of creative dissatisfaction, he took mushrooms in Big Sur and, naked and alone in a tall tree, had an epiphany: “Just be me. The real me. The sarcastic, overcompensating asshole.” He concluded, with simple awe, “It just never occurred to me to write like myself.” When he returned from the other side, newly convinced that his deepest self was actually the one on the surface, he’d chosen a name for this new persona: Father John Misty. “No!” one of his friends begged him, according to The New York Times. “Do not call it that.”

And yet since its debut, on 2012’s Fear Fun, that name has come to be much more widely known than J. Tillman. Father John Misty’s “breakout moment” (one of those music-industry phrases at which he would theatrically roll his eyes) was 2015’s excellent, hilarious, and surprisingly poignant I Love You, Honeybear, an admirably self-incriminating record about love, monogamy, and marriage. (It was a hit, though by indie standards; six months after its release, Billboard reported that its vinyl sales were some of the biggest of the year.) Misty has since given memorable performances on Colbert and Letterman (my favorite is “Bored in the USA”); last month, he made his Saturday Night Live debut, performing “Pure Comedy” and “Total Entertainment Forever” to the largest audience of his career. He has played a heartthrob in a Lana Del Rey video and maintains a semi-active side hustle as a pop songwriter; most notably, he has a writing credit on Beyoncé’s “Hold Up,” as well as “Come to Mama,” one of the best songs on Lady Gaga’s most recent album, Joanne. (His demo version of that song is particularly great.) In a recent Rolling Stone interview, he elaborated on his pop process: “If it’s vague enough, narcissists can project. They need blank surfaces to project onto. And we are living in a narcissist culture, so it makes perfect sense.”

A canny, demographic-straddling self-creation, in 2017 Misty is now the merry prankster of the all-too-self-serious indie rock world and a roguish confessor from inside the pop songwriting factory. His sense of humor is unsparingly sharp and meta: He has used every opportunity on Pure Comedy’s press tour to make the kinds of banalities we take for granted about musicians on press tours seem incredibly strange. He gave a deliciously awkward interview on a BBC morning show and a Eurovision-esque performance on German TV. After one bon mot, he told a Times reporter, “I love the exhilaration of feeling a pull quote come out of your mouth. The words just taste better.” Here is something he said to Pitchfork a few weeks ago:

Old Uncle Jerry has been walking the third rail of internet-outrage-bait like a tightrope the past few months, delighting in saying all the things you’re not supposed to say about pop culture right now: that female pop stars are not real feminists and that there is a difference between “entertainment” and “art” and that Lorde sucks. Or … maybe he is not saying these things, not really — maybe he is just mocking people’s tendencies to be so deeply offended by them. He noted later in that Pitchfork interview, “People have been saying to me since I was a kid, ‘I can’t tell if you’re being serious or not.’”

Up until now, this is-he-or-isn’t-he-fucking-with-us dynamic has afforded him a playful sense of freedom in his music; it allows him to embody, and exaggerate, an impish but literate persona. On Pure Comedy, though, this attitude sometimes tethers him to the kinds of concerns he’d like to transcend.

If Pure Comedy were a movie, it would be the first 10 minutes of Wall-E. There is something cluttered and postapocalyptic about the world as described by our odd extraterrestrial narrator: Some of his pet names for the earth include “this godless rock that refuses to die” and a “bright blue marble, orbited by trash.” (Just as verbose is the title of this song: “Things It Would Have Been Helpful to Know Before the Revolution.”) But these barbed lyrics are not sung with bitterness or rage; instead, they come in the middle of a song as sweetly sad and acceptably pretty as an Elton John tune.

“There’s a fricative disconnect between what Josh is saying and the way he’s saying it,” the composer Nico Muhly (who worked on string arrangements for the album) recently told The New York Times. Misty makes, in Muhly’s words, “lovely folk music, with a real attention to harmony, but it also insists on the lyrics being difficult to listen to. It’s sort of a Trojan horse of emotional content.”

That window dressing of traditional folk-rock is also why some SNL viewers probably did not even realize that, in the opening lines of “Total Entertainment Forever,” he sings the semi-provocative lyric, “Bedding Taylor Swift, every night inside the Oculus Rift.” Plenty of people on the internet did, though: The next day, the Rolling Stone headline read, “See Father John Misty Sing About VR Sex With Taylor Swift.” That same day, (in the requisite language of internet outrage) he “addressed” the lyric: “Human civilizations have been entertaining themselves in disgusting ways all throughout human history,” he said, and that although he “[didn’t] want that to happen to Taylor Swift … if you don’t think that this virtual reality thing isn’t going to turn into sex with celebrities, then you’re kidding yourself.”

Of course, he was being a little bit coy: Someone as celebrity-literate as Misty couldn’t possibly be ignorant of the whole fracas surrounding another song that featured a lyric about hypothetical sex with Taylor Swift — Kanye West’s “Famous.” Although, when pressed about it, he’s denied that his and Kanye’s lyrics have much in common: “If you can’t see the difference between those two lines,” he told one interviewer, “then you are a bullshit music writer.” Fair enough — after all, the part of “Famous” that supposedly upset Swift was not the boast that Kanye “might still have sex” with her, but the assertion that he “made that bitch famous.” You can come for Swift’s hypothetical virtue, but do not fuck with her claim to fame. (Also, $10,000 says she does not know who Father John Misty is.)

Still, I don’t mind Misty’s Taylor Swift lyric. It’s a succinct and provocative way to begin a song about a large, unruly idea: that modern technology will soon be able satiate our desires so completely that it runs the risk of numbing the humanity right out of us. The world the song describes is reminiscent of something David Foster Wallace predicted in Infinite Jest, which partially revolves around something called “The Entertainment,” a bit of content so perfect that it literally entertains the viewer to death. Pure Comedy reminds me of Infinite Jest in other ways, too — and not only because they are both overly long things that guys in bars will reference to impress people whether they have finished them or not. Both are also works of high, self-conscious intellect that perform feats of verbal and philosophical gymnastics before discovering — much to their anti-sentimentalist chagrin — that the clichés and banalities of people they once considered stupider than themselves actually turned out to be incredibly wise. “I hate to say it,” Misty admits, to great emotional effect at the end of the title track, “but each other’s all we’ve got.”

One of the best Father John Misty songs is called “Holy Shit.” It was on his last album, I Love You, Honeybear, and it is basically a valiant attempt at making poetry from the junky buzzwords that populate our modern vernacular. One of the verses goes like this:

It is, actually, a beautiful song — not just because of its lovely arrangement and lilting melody, but also because it ends with a lyric of hard-won tenderness: “Maybe love is just an economy based on resource scarcity / What I fail to see is what that’s gotta do with you and me.”

Honeybear remains the best thing Misty’s ever done: It was a record that moved methodically through cynicism and ugliness to prove, with an almost mathematical precision, that even in this trash heap of a modern world, true love does still exist. The confines of a “concept album,” even in the loosest sense, allowed him to drill deep. And although Pure Comedy certainly has its brilliant moments, the problem with it is that its scope is so wide that it must necessarily sacrifice some of the depth and focus Honeybear had. He’s great at diagnosing the ills of the modern world, but Comedy is a harder pill to swallow because it doesn’t quite pull off that “but here is the reason to go on anyway” moment that made the end of Honeybear so cathartic.

On several songs, though, he pulls off the impressive feat of being both panoramic and particular. Pure Comedy’s boldest achievement is “Leaving L.A.,” a 13-minute centerpiece of softly strummed self-examination. It’s Misty at his most meta, which is to say it is the most accurate litmus test of whether you appreciate Misty being Misty: “Oh great, that’s just what we all need,” he sighs. “Another white guy in 2017 who takes himself so goddamn seriously.”

Just as lacerating, though, is a shorter song called “The Memo.” “As the world is getting smaller, small things take up all your time,” he sings. “Narcissus would have had a field day if he could have got online.” As the song goes on, it gives the impression that it is digitally decaying; a distorted robot voice says, as though reading a YouTube comment from a listener who found the song via some kind of cold-blooded algorithm, “This guy just gets me.”

One of the simpler songs on Pure Comedy is “Birdie,” a quiet dirge sung over backward tape loops, imagining humanity as glimpsed from, well, a birdie’s-eye view. “Are you really as free as all the great songs would have me believe?” Misty asks.

Pure Comedy left me with an itch to hear one of those “great songs” to which “Birdie” clearly refers: “Bird on the Wire,” written and originally recorded by Leonard Cohen, but covered by so many artists over the years that when I typed it into the cold-blooded algorithm it gave me a whole variety of versions of human yearning to choose from. “Bird on a Wire” is basically a standard at this point. Johnny Cash sang it on American Recordings, his first late-period collaboration with Rick Rubin. Tim Hardin did a gorgeously soulful version of it, released near the end of his career, about nine years before he died troubled and too young of a heroin overdose. The Neville Brothers do a stirring interpretation. So thoroughly has “Bird on the Wire” traveled through the cultural cosmos that Katey Sagal, the actress who played Peg Bundy on Married With Children, sang it during a pivotal scene in the TV show Sons of Anarchy. Although Cohen’s original version of the song was just three and a half minutes long — the standard, oft-dismissed duration of a pop song — it also contained some of the weirdness and hyperspecificity to which Father John Misty aspires (“Like a worm on a hook, like a knight from some old-fashioned book / I have saved all my ribbons for thee”). It contains enough of that “blank surface to project onto” — you know, the one that Misty either earnestly or ironically derided — that plenty of artists of different genres, genders, races, and ages have felt compelled to see in it their own “capital-H Humanity.”

It is perhaps unduly harsh to fault “Birdie” for not being as good a song as “Bird on a Wire” — how unfair to fault an artist for not being Leonard Cohen. But Father John Misty swings so wide on Pure Comedy that these are the kinds of comparisons he sets himself up for. Cohen is indeed a kind of spiritual father to Misty, who in concert has given lap dances to “I’m Your Man” and in song has described himself as “The Only Son of the Ladiesman” — and there are plenty of master songwriting lessons to learn from him, like how to do more with less, and how you can be the most eccentric and odd version of yourself in songs while still making room for the feelings and experiences of other people.

Misty is an excellent songwriter, an imaginative lyricist, and a nobly silly provocateur in an industry that takes itself way too seriously. I only wish sometimes he’d let all that be enough, and, in his songs, get out of his own way a bit — find a way to move through a sense of haughtier-than-thou isolation and use his songs and talents as vessels for real connection. The sense of warmth and generosity that he achieved on Honeybear and here achieves in stand-alone songs like “Pure Comedy” evade this record when you take it in as a whole. Perhaps these are petulant nitpicks for an artist trying to carry the weight of the entire world on his well-tailored shoulders. Pure Comedy is an imperfect record, but Father John Misty aspires to a hell of a lot more than you can say of most artists these days: He has tried, in his way, to be free.