Father John Misty presents a sprawling double-feature: the skewering of an infantile generation, and the self-skewering of its author. From the mind of an apocalyptically inclined neurotic, who reads Žižek and Freud and believes humanity is condemned to moral chaos, comes Pure Comedy, a grueling, often inspired odyssey that screams to be taken as art. Across its 75 minutes, humility is scarce. In one song, having indexed the species’ flaws, he reprimands God: “Try something less ambitious next time you get bored.” It is intense, fatalistic, exhausting, and grandiose—sometimes devastating, sometimes pretentious. (Regarding love—he’s not really doing that anymore.) So yes, it is a Father John Misty album, and Josh Tillman still excels at tormenting those unlucky souls who enjoy his music.

The record is also Tillman’s first opportunity to confront pop culture from the frontline. After releasing I Love You, Honeybear, whose inquiry into romance and masculine folly won many hearts, he coasted through the last two years as an indie firebrand. He perfected theatrical cynicism, sarcastically covering Taylor Swift, trolling music sites, claiming responsibility for a stolen crystal and using the coverage to denounce health food. He shot a video with Lana Del Rey, who shares something of his postmodern mystique, and wrote for Lady Gaga and Beyoncé, who do not.

That behind him, the Pure Comedy circus kicked into gear at a New Jersey music festival last July. Instead of his songs, Tillman performed a rambling soliloquy, triangulating Trump anxiety, the obstetrical dilemma hypothesis, corporate evil, folksy escapism, and the “fucked up entertainment complex.” Along with all those themes, Pure Comedy channels the speech’s righteous delirium, a rhetorical mode Tillman finds irresistible. If his confessions favor ironic distance, his big-picture theses exude something close to rapture. “The Memo,” a highlight here, smashes together cynicism and compassion, with Tillman declaring that it’s “not self-love that kills you,” it's when “those who hate you” are allowed to profit from your vulnerability. Such sermons are typically repelling, but what saves him from insufferable smartassery—for the most part—is his ability to turn yelling at clouds into a grand form of entertainment.

Pure Comedy follows the thread of Honeybear outliers “Holy Shit” and “Bored in the USA.” The latter concealed sincerity beneath melodrama, its mockery of “middle-class problems” complicated by troubling reflections on depression. Those uncomfortable collisions—bourgeois ills explored through otherwise sympathetic characters—emerge throughout Pure Comedy.

Beneath Pure Comedy’s synth-dappled country, blue-eyed soul, and pop fashioned after George Harrison is a battleground filled with religion, pop culture, technology, and neoliberalism. To open “Things It Would Have Been Helpful to Know Before the Revolution,” a wonderful portrait of life after the climate apocalypse, Tillman nonchalantly topples capitalism: “It got too hot,” he sings, “And so we overthrew the system.” Midway in, an orchestral cacophony swirls into an outrageous chorus, which I’m sure Tillman would love to see quoted unabridged:

“Industry and commerce toppled to their knees

The gears of progress halted

The underclass set free

The super-ego shattered with our ideologies

The obscene injunction to enjoy life

Disappears as in a dream

And as we returned to our native state

To our primal scene

The temperature, it started dropping

And the ice floes began to freeze”

The indulgence is pure Tillman. But the passage, in all its mad glory, matches the size of the task, particularly in times of total dysfunction. It’s never been easier to sympathize with Tillman’s pomposity. Only in the song’s conclusion does the façade collapse, as “visionaries” start developing products that will rejoin this new society with capitalist realism. A cop-out, maybe, but who else would have copped in to begin with?

While “Revolution” is its least discreet flirtation with utopianism, Pure Comedy makes plenty of time to call bullshit on visionary capitalism. The title track swirls with religious fanaticism, secular ideology, and pharmaceutical greed into a repudiation of almost everything. In the last chorus—“But the only thing that they request/Is something to numb the pain with/Until there’s nothing human left”—the record hurtles into a chronically pleasurable near-future. “Total Entertainment Forever” is a postcard from the brave new world: Backed by sarcastically ecstatic horns, Tillman celebrates a “permanent party” where our appetite for distraction has eroded the old-fashioned human soul. His characters finish the chores, slide on the Oculus Rift, and jump into bed with the pop star du jour. He heralds the “freedom to have what you want” in a tone that suggests freedom, whatever it may be, does not look like this.

After that opening suite—“Pure Comedy,” “Total Entertainment Forever,” and “Revolution”—the music settles into a tonal plateau. Even the most gripping songs unspool with acoustic leisure, and they can be long and lofty trips. The spiritual anchor is “Leaving LA,” in which fragments of orchestral splendour—all arranged by the brilliant Gavin Bryars—are buried beneath a 13-minute pilgrimage through Father John Misty’s psyche. An unappetizing prospect, perhaps, but he writes captivating scenes; one revisits a traumatic childhood saga soundtracked by Fleetwood Mac’s “Little Lies” in a JCPenney, another a New Year’s sunset that “reminds me, predictably, of the world’s end.”

Five verses into the song, Tillman inserts a mocking female character: He’s just “another white guy in 2017,” she groans, “who takes himself so goddamn seriously.” “Leaving LA” reaches for transcendent honesty, but this lyric feels misjudged. Is this a sincere concern or an attempt to shoot down nonexistent thinkpieces? Father John Misty’s music is certainly exasperating, but it’s not due to his entitlement so much as that irrepressible impulse to outpace the listener’s criticism. The moment somebody says, “I know I’m being annoying” is often when you realize it’s true.

Tillman has, of course, anticipated this critique. His childish desire to be loved or hated on his own terms is dredged up on “A Bigger Paper Bag,” but there’s an added, delicate touch that’s endearing. “It’s easy to assume that you’ve built some rapport/With someone who only likes you for what you like yourself for,” he sings, over a woozy arrangement evoking peak Elliott Smith. “You be my mirror/But always remember/There are only a few angles I tend to prefer.” It’s a rare callback to Honeybear’s psychological burrowing, and I find myself returning to it. His sociological bombast is dwarfed by these quiet revelations.

The scarcity of such interludes doesn’t undermine the Misty manifesto, but it does mean the record’s pontifications, particularly the tired false equivalencies of “Two Wildly Different Perspectives,” can test your patience. David Foster Wallace—whose critiques on irony, entertainment, and self-consciously “hideous men” are all over Pure Comedy—once advocated for bleak fiction in dark times. Wallace said that it should “find a way both to depict this world and to illuminate the possibilities for being alive and human in it.” This redemptive spirit eludes Tillman. Given his off-record provocations—that a pop star’s “wearing next to nothing” strips her music of value, for instance—it’s reasonable to expect him to dream up something for us to really care about (or at least to button up his shirt). He instead settles on soothing defeatism, a litany of conquered crises whose lessons amount to, “That’s just the way it is.” Given the album’s thematic largesse, it’s almost charming. Almost. But you wonder what kind of progressive future he envisions: that which will lift society or merely flatter his own intellect.