On his fifth album, “Chloë and the Next 20th Century,” Joshua Tilman, who goes by the stage name Father John Misty, turns to Harry Nilsson and the jazz standards of the early 1900s for an esoteric romp through his ever-eclectic observations on life. Somewhat more direct than his recent work — “Pure Comedy” focused on an expansive exploration of humanity’s nihilism — his writing here concentrates on evoking delicately crafted characters and quietly moving miniature stories. Tillman fully commits to the throwback jazz sound he’s flirted with in the past. The result is a bass- and string-heavy record that feels more suited to a smoky jazz club than to his usual folk-focused crowd.

Tillman has always sung about people with an observant sense of distance from their reality, but on “Chloë and the Next 20th Century,” his fascination with humanity takes a more active role. In the past, he’s been criticized for his overly opinionated and didactic lyrics, but here, it’s much easier to parse out his subjects and his relationships to them than his thoughts on the meaning of it all.

On “Goodbye Mr. Blue” — the closest thing to a conventional folk song on this album — Tillman laments to his ex-lover about the death of their once-shared cat. While still featuring his distinctly sardonic lyricism, this track’s fantastic production and arrangement — complete with oozing, slippery, sliding guitars and hypnotically repetitive picked patterns — also uncannily sounds like a ’70s Harry Nilsson record. As Tillman sings “That Turkish Angora is ’bout the only thing left of me and you” and “Mr. Blue died in my arms, nothing they could do / Don’t the last time come too soon?” this track straddles the line between hilarity and a movingly specific portrait of human love and loss.

“(Everything But) Her Love” and “We Could Be Strangers” both feature odd, winding duets of marimba and upright bass that recalls the Beach Boys’ “Pet Sounds.” Throughout the record, these instrumental experiments push Tillman further away from his intimate piano and tightly constructed acoustics. This move toward a jauntier, wilder sound keeps some of the weaker songs surprising.

However, the next track, “Buddy’s Rendezvous,” is a stunning return to Tillman’s conventional balladry. Backed by rich lyricism, the addition of a saxophone maneuvering around his vocals makes this song one of the firm standouts on the album. Singing of the track’s titular tavern, the fatal consequences of unpaid debts, and failing as a father to his fictitious daughter, Tillman sings “So you’re gonna be a singer / Well I’ll be, goddamn / You’re as pretty as a postcard / No thanks to the old man.” This track feels nearly perfectly constructed and arresting in its woundedly disaffected emotional power. It’s an instant classic in an already impressive oeuvre.

The pre-album single “Q4” remains a sparking harpsichord-driven orchestral ballad, charting the trials of a fictitious author who pilfers from her late sister’s life and provides a much-needed lift in energy at the record’s midpoint. “Olvidado (Otro Momento)” is a finely done — if not somewhat puzzling — detour into salsa, sung partially in Spanish. Although a little bit too out of place for the already scattered soundscape on “Chloë,” it is executed well enough to remain intriguing. 

As he often has on his releases, Tillman saves the best for last with album closer “The Next 20th Century,” which is undoubtedly the album’s centerpiece. Tillman preaches of the coming apocalyptic future with all the disaffected swagger of an ’80s Leonard Cohen cut. A similarly Cohen-esque drum machine — coupled with quietly shimmering acoustic instrumentation — creates a disorienting sound. 

The track joins the rest of Tillman’s fantastic catalog of six-minute-plus epics, covering Val Kilmer, Buddishm and the futility of love in the modern world, all in a devastating package tied together by a brutal fuzzed-out guitar solo that hits out of nowhere. With lyrics like “I’ve seen him wearing aviators and a black baseball hat / Stalking airports ’cross the bardo quiet as a wildcat,” “The Next 20th Century” has to be some of Tillman’s most stunning writing to date.

Producer Jonathan Wilson — notable for his co-production contributions to previous Father John Misty records and his versatile work with Jackson Browne and Conor Oberst — helps unite the songwriter’s disparate influences into a finely tuned whole through his overall smoothing out of the sound. He keeps everything sounding at home on a Father John Misty album without really restraining any purposeful departures. While none of the songwriting on the album is by any means weak, Wilson seems acutely able to elevate some of the slower moments by infusing them with the warmth of a worn-out jazz record. 

Tillman’s lack of press appearances and sudden departure into Golden Age jazz make “Chloë and the Next 20th Century” an especially unexpected, though distinctly welcome, addition to Father John Misty’s catalog. Tillman’s experiments with jazz and big-band sounds are largely successful, as it feels like he’s adjusted his songwriting to match this new direction rather than trying to force it onto his existing style. The execution is sincere enough to never feel like any sort of pastiche or ironic gesture. 

While “Chloë and the Next 20th Century” is, in places, a smidge less consistently showstopping than his past releases, Tillman has set the bar high for himself as one of the best songwriters of the last decade. After the bleak vulnerability of 2018’s “God’s Favorite Customer,” “Chloë and the Next 20th Century” features some of Tillman’s most rich lyrics ever. The album offers a vulnerable look into Tillman’s relationships that brings a new dimension to his infamous persona.

Contact Holden Lay at [email protected].