The artist formerly known as Josh Tillman has taken fans through some twists before, but “Father John Misty: big band leader” is probably not a curve very many saw coming as a career development in 2022. The eclectic singer-songwriter certainly hasn’t been shy about employing orchestration before, to the point of bringing his own sizable string section out on tour on his last pre-pandemic outing, probably at considerable personal expense. But the strings are lusher now, he’s not just adding woodwinds and horns to the mix and, in his fifth “Chloë and the Next 20th Century,” he’s harking back pretty flagrantly at times to the (previous) 20th century’s first half, with at least some of the new songs steeped in the popular music of the ’30s and ’40s.
It was really anyone’s guess how Misty delving into pre-rock pastiche territory might go, given that he never showed that huge a bent toward musical nostalgia up until now, even when his literate indie-pop leaned toward the ornate. And his trademark existential concerns don’t really shout “Hey, let’s rub a little Tex Beneke on this.”
Or do they? “Chloë” works in a big way, once you’ve settled into the comfort of knowing the unique combination of dark themes and sometimes lighter music is not going to be an exercise in camp, even though a certain amount of irony definitely figures into it. Part of why it’s so successful is that Misty remains a moving target throughout the album. Only about half the songs are distinctly in that Depression/WWII throwback vein, while others employ the orchestration on tunes that fall more squarely into a ’60s/’70s singer-songwriter mode. And somehow, arranger Drew Erickson threads the needle between these two modes rather seamlessly, so you aren’t thinking you’re in a soldiers’ canteen one moment and chilling with Jimmy Webb and Glen Campbell the next, although that’s kind of what it comes down to. It’s as gorgeously arranged an orchestral-pop record as we’ve gotten in years, and whatever Misty paid Erickson and returning producer Jonathan Wilson to bring it all together, they should both get a raise.
But is there any overriding thematic reason why Misty wanted to bring these songs out of an indie chamber-pop realm and right up onto the bandstand? There are some that can be fathomed, but let’s say right off the bat that this is Misty’s most mysterious record, even though it looks on paper like it ought to be his most peculiarly definable. Gone, for the most part, are the grand statements about the meaning on life — or the lack of it — that characterized his signature album, 2017’s agnostic masterpiece “Pure Comedy.” But also absent, for most intents and purposes, are the more personal, grounded reflections that made 2018’s “God’s Favorite Customer” feel like his most autobiographical album as well as his most accessible. “Chloë and the Next 20th Century” comes off as a collection of ciphered short stories in which we’re usually learning only about two-thirds of what we need to properly suss the narrative. That’s OK, though — some of the details he provides are so literal that they’re LOL funny, and he even shares some blatant philosophical asides, so you’re never feeling cheated, even if you’re confused.
If I had to guess why Misty/Tillman went so retro with some of these songs, I’d venture to say it could have something to do with how many of the women in these songs — starting with Chloë herself, in the album opener — appear to be deeply charming socialites without a precise moral compass. So maybe it’s an album with a lot of Daisy Buchanans, leading Misty to envision himself as a bit of a smitten Jay Gatsby, or at least a note-taking Tom Buchanan. “Chloë is a borough socialist / She insists there’s not much more to it / Than drinks with a certain element / Of downtown art criticism,” he sings in the opening stanza, setting a certain kind of male-gaze mood right at the outset. It turns out the titular woman is a not just an object of desire for the narrator but a source of prescription drugs: “How Benzedrine’s supposed to address / Your shoplifting’s anybody’s guess,” he sings in one of those aforementioned laugh lines. He’ll admit that “her soul is a pitch black expanse,” and concede some worries about a couple of previous lovers that seem to have met with fatal accidents. At the end, someone seems to take a dive off a balcony, although it’s not entirely clear whether it’s him or her. Anyway, the cheerfully Glenn Miller-esque tune assures us we shouldn’t fret too much about either party’s fate.
And then, just as quickly as “Chloë” has set listeners to thinking that this is going to be an album of flapper-invoking fun, the record makes an instant 180 with the second number, “Goodbye Mr. Blue.” The title figure in this one is a beloved cat, which expires over the course of the song, paralleling the slow death of the relationship between its two separating care-keepers. You don’t have to be a cat person to get just how sadcore this song is going to be, even if there’s a trace of underlying wit in the way Misty draws out the details of this couple having used up all of its nine lives. Anyone who’s been in a divorce will recognize the emotional details, if not the specific cat food invoked: “We used to lay around just laughing at what these freaks out there were trying to prove / Well, what’s wasting time if not throwing it away on work / When the last time comes so soon.”
The music on that one couldn’t be less stuck in the big-band era. The finger-picking guitar places it more in the time of Fred Neil and “Everybody’s Talkin’,” and although the strings on it are no less blatant in the arrangement than anywhere else on the record, they’re in the realm of the spookier moments of Bobbie Gentry’s first couple of albums, or something Van Dyke Parks would have come up with. And so in just a couple of songs has “Chloë and the Next 20th Century” established its breadth. Parts of the album are going to make you think of flappers. And parts of it will evoke “Nilsson Sings Newman,” in how a really lovely, calm tenor, Harry Nilsson, took on the really raggedy, rough-edged songwriting of Randy Newman, although Misty of course gets to assume both roles.
The material sometimes gets more cryptic than there… although, in one case, it’s much less. As idiosyncratic as most of the songwriting is, there’s one completely straightforward number in the mix that has to be the most straightforward piece he’s ever written, or at least released. That is “Only a Fool,” which, although it has a light-swing arrangement, sounds at its core like something Willie Nelson or Harlan Howard might have written for Patsy Cline in the countrypolitan era. “I couldn’t fathom way back when / How I’d long to have you break my heart time and again,” he sings with his heart so plainly on his sleeve, in language so simple, it’s like a ghost from Music Row past has possessed the usually wordier Misty for a few sweet minutes.
Not to worry — the weirder Misty will return. That happens in a big way with the album climax, the nearly seven-minute “The Next 20th Century,” which is the one track on the record that doesn’t seem to have a foot in any other era than our own; it even has a noisy squall of electric guitar a few minutes in that’s highly uncharacteristic of anything else on it. The mood is lovely, but increasingly doom-laden, as Misty uses a couple from apparently different racial backgrounds as the starting point for a stream of consciousness about ancestral strife and the inevitability of human disaster, with nothing learned before death leads to the next turnover of generations. I think Misty is trying to put a slightly positive spin on things at the end of this magnum opus — “I’ll take the love songs, and give you the future in exchange,” he sings, possibly providing a raison d’etre for doing an album that invokes the past. But it still might be the most depressing song he’s ever written, which, for Misty, is saying something.
But oh, what fun we’ll have in getting there! And that darker-than-dark capper doesn’t do anything to erase the material along the way that does have some mirth to it. That includes the first single, “Funny Girl,” another one of the album’s pre-rock pastiche numbers, which details yet another obsession with a social butterfly, this time an actress who “charmed the pants off Letterman.” (Fans have wondered if this song is a roman a clef about a real celebrity Misty was infatuated with, and maybe it is, although he is careful to place an amusing detail about how she is “doing interviews for the new live-action Cathy” to place it in the realm of period fiction.)
Of course, the music video for “Funny Girl” made the intent of the tune completely transparent by… having a digital jellyfish as its star. That’s an example of how Misty (who has not been out there asserting himself in the press lately) doesn’t intend to make anything about “Chloë and the Next 20th Century” too easy graspable, even though there are about a thousand delightful things about it to make you want to latch on. He’s elusive even in the midst of taking on a new musical persona that seems high-concept. But it’s that combination of intriguing opacity and occasional open-heartedness — and his twin inclinations between deep philosophizing and deadpan comedy — that give “Chloë” the oddball breadth to be one of the best albums of the year.