Early last November, a handsome, bearded songwriter going by the name Father John Misty appeared on "Letterman" to perform a ballad called "Bored in the USA". Blazer pressed, shirt-collar open and eyes shut tight in concentration, Misty, whose birth name is Josh Tillman, sat at his grand piano, that great totem of solitude and opulence, wringing out lyrics so alienated you wondered how he made it out of his yurt, let alone to the spotlit world of late-night TV.

After a line about his own irrelevance ("By this afternoon I'll live in debt/ By tomorrow, be replaced by children"), Tillman turned away from the piano and took center stage. Magically, the piano played on without him. Strings swelled, lights glowed with multicolored gels, Tillman put one fist to his hip and pouted like a glam doll—it was all an act, and why should we have expected anything else? As the song plowed into its bridge—"They gave me a useless education/ And a subprime loan/ On a craftsman home!"—laughter filled the room. Canned, of course: How could anyone laugh at someone so miserable, and about such shallow, middle-class problems? The audience took a second to decide whether or not they should clap.

"Bored" is one of 11 songs on I Love You, Honeybear, an album by turns passionate and disillusioned, tender and angry, so cynical it's repulsive and so openhearted it hurts. Misty is at root a folksinger: Someone who uses natural-sounding arrangements and first-person songwriting to give the audience the impression that he's revealing the depths of his soul, which in a fucked-up way, he is. Because he sings sweetly, you imagine him to be sensitive; because he plays the acoustic guitar, you imagine him to be closer to a naked, more old-fashioned way of life, one in which we might frolic in the grass unafraid. This is an artist whose origin story starts on top of a literal mountain, abetted by psilocybin mushrooms—the story of a seeker in earnest, the kind that sounds even more credible when told by someone who has a beard or used to be in Fleet Foxes. Tillman is both.

Not all the jokes on Honeybear are as funny as "Bored in the USA" and several don't even register as jokes. Tillman often seems to play a failed, bitter version of what you might expect him to be from his headshots—an Andy Kaufmanesque hustler whose seams don't just show, but are constantly in danger of splitting. What should be the sweet story of a one-night stand ("The Night Josh Tillman Came to Our Apartment") turns into a vicious, nitpicky list of his conquest’s faults, while a bar night ("Nothing Good Ever Happens at the Goddamn Thirsty Crow") becomes a tirade against a guy trying to hit on Tillman’s wife. "Why the long face, jerkoff?" he spits. "Your chance has been taken/ Good one." For someone fond of glockenspiels, Tillman says the word "fuck" a lot.

Tillman is a wordy writer. At times, the music on Honeybear almost acts as a palliative to his lyrics, blunting the edges and keeping the mood friendly enough to get you from one excoriating piece of satire to the next. Fans of the Beatles and Sufjan Stevens will find that songs from Honeybear sit comfortably in their Spotify "Mountain Drive" playlists; fans of stand-up comedy will find the album as thorough, sad and bitterly cathartic as any good hour-long special. For all his poetic undercurrents, Tillman is a showman that way: He knows how to get his message across in a form people can clap to.

Honeybear is conflicted music that leaves me with conflicted feelings. Tillman is funny, but his humor is driven by meanness and self-loathing; he’s sweet, but he can’t manage to say anything nice without smothering it in jokes, like a dog compulsively trying to cover up its own shit. He opens the album by forecasting the apocalypse but most of the time comes off as the kind of mystic who gives up and embraces the debauchery, the patrician in some yoga sex ring, a bimbo Nero who fiddles while Los Angeles burns and occasionally gets sidetracked gloating about how hot his wife is. Yes, he gets high, but he never really leaves the dirty, dirty ground.

In the end, his sincerity is a sharper weapon than his humor. Honeybear’s last couple of songs in particular—"Holy Shit" and "I Went to the Store One Day"—arrive at the strange clarity people sometimes feel in the wake of drug trips, where life’s simplest lessons are suddenly presented to you, quiet and nude: Love people, stay open, be real. Admittedly there are an infinite number of barriers to these ideas, not least of which nobody seems to agree what the words "love," "open," and "real" actually mean, but my guess is that Tillman would acknowledge that failing isn’t as important as never trying at all.

Despite attempts to draw lines between himself and his persona, the story of Honeybear is at least in part a story of Tillman’s own recent marriage, which seems to have slowed his pace and made him reconsider questions of intimacy and closeness, the way marriage can do. The album ends with what were apparently his first words to his wife: "Seen you around. What’s your name?"—a question asked without editorializing. A few lines earlier, he had us at the brink of their deaths. "Insert here," he sings plaintively, "a sentiment re: Our golden years." I’ve chewed on that moment for a while now, feeling alternately as though it was a cop out and as though his point might be that trying to compress his and his wife's future into one line would be corny and disrespectful. At least I know he means it when he says he isn’t sure what to say.