Here’s a brief and highly incomplete list of 30-plus song albums: The Beatles’ 1968 White Album, weighing in at a tight but nervous 30 on the nose. Neil Young’s career-spanning-to-date 1977 collection Decade, checking in at 35. The Clash’s immersive 1980 cross-cultural dreamscape Sandinista!, doing one better at 36 tracks. Add to this number Jeff Tweedy’s own 30-song hippie-jazz-pop-odyssey Twilight Override, which brings together the sundry threads of the now four-decade-long career of one of our great melodicists and oversharers. At 58, at the height of his stature and creative ability, he remains irritatingly ambivalent and unknowable and funny and compelling in equal measure. Come to think of it, the album Twilight Override resembles most is Bob Dylan’s 1970 contract-breaker-panic-attack double LP, Self Portrait—widely derided at the time but profoundly hilarious, melancholy, and rewarding—which, at 24 songs, wandered between weird new compositions and obscure covers. Twilight Override is comprised of only strange, beautiful, and threadbare originals, but the sense of glorious indulgence is straight 1970 Dylan. What is this shit? How much time do you have?

Tweedy. The Randy Newman of maximalism—thrilled to offload the dumptruck of his mind at any interval, arguably with no editing—but of course this one is on us, having reveled in the long-form permissiveness of Being There and Summerteeth and the double disc Tweedy-family-band album Sukierae, and yes, even the sanctified Yankee Hotel Foxtrot with its recent reissue—11 different versions sequenced different ways, on different mixing boards, all telling a different story about a great album that was itself probably a couple of tracks too long. We bought it all, by which I mean we purchased it at Record Store Days and on special offers. Or at least I did. Twilight Override is the inevitable end point. It is the thing he was always ramping up to.

And it’s pretty great. The antsy minor key opener “One Tiny Flower” starts off evoking the overlooked Paul Westerberg solo classic “Even Here We Are,” before evolving into the sort of jam you might have heard in the more pastoral moments of All Things Must Pass. “Caught Up in the Past” drifts into Tweedy’s too-occasional Todd Rundgren mode, with a lilting keyboard hook and fetching harmonies enlivening yet another meditation on dark portents and parting clouds. “I get so far behind/I forget I’m following,” he avers in his by-now indelible raspy warble—another of his peculiar, Zen-adjacent koans that double as bracing self-assessment. “The ashtray says/You were up all night,” he once told us, like the ashtray was narcing on him. He has a tendency to indict inanimate objects, as he does on the sedative-funky “Mirror,” which suggests something like Al Green backed by Eric’s Trip and makes an unlikely miracle of the intuitively obvious couplet observation: “You are a mirror and the face/You are an object and the space.”

Twilight Override is built to be immersive rather than visceral. We are along for the journey, but wary of the thrills. Gas, grass or ass. Lots of cries, lots of laughs. The vogue for Freudian therapy—the once a week, lay on the couch, dig into your childhood stuff—has long since fallen out of favor with the wider psychoanalytic community, replaced by generally faster, less expensive, more efficacious approaches like CBT. Based on the evidence provided by Twilight Override, no one has informed Jeff Tweedy. To the contrary, we are in for the long version—he has felt blank, he has eaten wedding cake, he has seen the expansive Western sky at dusk—the world is too much with him, late and soon. But there is so much splendor too. On the swelling, string-driven “Stray Cats in Spain,” he sees stray cats in Spain, or possibly, rockabilly revivalists the Stray Cats. In either case, it is an epiphany bordering on a religious experience: “Oh what a beautiful day,” Tweedy sings, summoning the quivering awe of his “Ashes of American Flags” tenor. He is increasingly attuned to the static-y emotional frequencies of Robert Hunter, where the overlap between bone-deep fatigue, desperate yearning, and the possibility of ecstatic deliverance bind together in a gloriously wobbly existential dance. Like Hunter, he perceives the sublime in the prosaic. When Tweedy sings: “Stray cats in 2019, rocking in the street,” his question-mark vocals suggest one who can’t quite believe he’s witnessed something so transportingly magnificent.

He won’t be your mirror, but he’ll show you where to look. Twilight Override is frequently funny, as on the jaunty “Lou Reed Was My Babysitter,” where he sings lines like “I want you to blow smoke in my eyes” with Lou-worthy lasciviousness, a worthy update to Jonathan Richman’s positively perfect tribute. “KC Rain (No Wonder)” sounds a little like Cat Stevens’ Tea for the Tillerman subjected to shock therapy. The beguilingly weird chamber-pop of “Love Is for Love” evokes the 1970 classic Vintage Violence, as if John Cale had been his babysitter too. On the Sister/Lovers-like “Too Real,” Tweedy lays bare his deepest anxieties behind a tremulous wall of delay reminiscent of the brilliant 4-track recordings of F.M. Cornog’s East River Pipe and Jack Logan’s Bulk. Thus born, the ghosts are everywhere. Infamously, cruelly, Dylan once told Phil Ochs: “You’re not a folk singer, you’re a journalist.” Or was it so cruel? Tweedy is a journalist of the soul, always hunting down those sad-ashtray leads.

Tweedy can be a trickster, and he is undoubtedly having fun with our collective sense of music history: One doesn’t place a song called “Cry Baby Cry” on the sixth side of a three-album set without knowingly evoking the Beatles chestnut lurking near the same spot on the White Album. But with its magnetic powers of accumulation, Twilight Override is doing much more than mining posterity for Pavlovian crate-digger reveries. In a press release, Tweedy addresses the audacious length of the album: “What I really want to do is grow my heart big enough to love everyone. And if I want a heart big enough to meet this moment, it requires something expansive.” What does he mean, “to meet this moment?” What about this moment would anyone possibly want to meet?

Having recently caught Wilco at the Outlaw Music Festival’s Long Island date, on a bill with Dylan, Lucinda Williams, and Willie Nelson, I thought how far we had come from Uncle Tupelo, the Gen X CCR, to this beautiful outdoor pavilion night. They played “Box Full of Letters” and “Handshake Drugs” and “Impossible Germany” and finally a completely convicted version of “U.S. Blues” that set the Jones Beach Theatre on fire. Later Tweedy was onstage for Willie’s jaw-dropping, show-stopping singalong of the Carter Family’s “Will the Circle Be Unbroken.” The bleachers shook; the world was momentarily put to rights. All throughout Twilight Override there is a feeling of grasping and tumbling and reassessment. The last track on the album is appropriately called “Enough,” and interrogates the entire meaning of the enterprise: “Has it ever been enough/Has it ever been okay?” Twilight Override is one hour and 51 minutes long. That’s how big Tweedy’s heart has grown. It’s a stemwinding and sometimes treacherous trip. At times it can feel like he’s trying to break our heads.

But he is a humanitarian if not always an optimist. There is a deep generosity to Twilight Override’s stubborn refusal to see the world through the demoralizing lens of these miserable times. If there’s a concept to the record, it’s about punching through the darkness, keeping on keeping on. Only then, and only maybe, might you live to reveal that next, glorious stray cat horizon. That’s what being there is all about.