Singer-songwriter Jeff Tweedy is at that age when most people have begun to take serious stock of where life has brought them. He’s learned a thing or two about how to approach uncertainties and what really is most important. At 58, he’s a longtime husband and the father of two adult boys, Sammy and Spencer, who also play in his solo band and helped craft his beguiling and introspective new triple album, “Twilight Override,” which is earning some of the best reviews of his career.

For anyone unfamiliar, Tweedy is a pioneering figure within the alt. country/rock scene, having made an early mark with Uncle Tupelo before launching the adventurous Chicago rock band, Wilco, which arrived as a major critical and popular success with its fourth album, “Yankee Hotel Foxtrot.” (Crazy to remember how old that album is now; it was streamed for free seven days after its originally planned Sept. 11, 2001 arrival date. I can remember voting for it in The Village Voice’s Pazz and Jop critics’ poll, where it won first place). On the follow-up, “A Ghost Is Born,” Wilco nabbed its first Grammy for best alternative music album, and the band has continued to tour heavily ever since behind consistently engaging records, playing a memorable, 36-song show at The National in Richmond in 2010 that included a closing cover of Big Star’s “Thank You Friends.”

What I like most about Tweedy is his raggedly soulful vocal delivery; his knack for delivering Lennon-esque melodies with a naturally weathered style all his own, in part because intense migraines have made him a lifelong puker, a corrosive effect similar to Lennon’s smoking and primal scream therapy. Tweedy also has an impressive work ethic and has maintained a busy solo career, crafting albums with gospel great Mavis Staples and guitar legend Richard Thompson, doing soundtrack work and writing books about songwriting. His latest solo album, “Twilight Override,” features 30 songs that immerse the listener in a nearly two-hour showcase of Tweedy’s natural ease shifting between intimate folk, catchy rock and spoken-word country. He and his family band are playing the Groovin in the Garden series at Lewis Ginter Botanical Garden on Saturday, Oct. 25, with an opening set by Liam Kazar, who also plays in Tweedy’s group.

A couple weeks ago, I had a brief, 15-minute Zoom chat with the singer just before his tour kicked off. Peeking over large, horn-rimmed glasses and chuckling easily and often, Tweedy came across as a friendly and engaging person, very down to earth, which made me like his new album even more. (Apologies, I did blow the first minute showing him an old photo I had of him at artist Fred Tomaselli’s studio in Brooklyn; they collaborated on “The Wilco Book,” though Tweedy notes they haven’t done anything together lately).

Style Weekly: Congrats on the new album, some beautiful songs on there. I just got it last Thursday. During the day, I listened to your two-hour album, then at night, watched the new Paul Thomas Anderson movie, which was three hours. So it was a good day, I got to experience two lengthy works of art. It made me think about the concept of the triple album as this world, not unlike a film, that one willingly enters into. What was your intention behind it?

Jeff Tweedy: It would’ve been high aspirations to consider it world building (laughs).

I just looked at it like: Spencer and Sammy and I had a long car trip, and we listened to [The Clash’s triple album] “Sandinista!” [1980] in its entirety. It was kind of a cathartic moment. That record is kind of a slog, honestly (laughs). But it was also mind blowing how ambitious it was, and how unique the sound of it is. Really, just the audacity of a triple album. Why is that audacious? I don’t know. But I think it just planted the seed: What would I do with a triple record?

I could see that if Wilco made a triple record, it would give us a lot of room to spread out and play some longer songs, give [guitarist] Nels [Cline] a lot of room to space out and things like that. But for me … I guess it is kind of like world building. It is kind of like getting to create an atmosphere and seeing how long you can sustain it in a way that feels welcoming and has some forward momentum that keeps people listening.

I think if it was going to be successful to me, it was going to feel like a really good collection of short stories. Or something where everything is not necessarily connected to one big story, but it all feels like it belongs together.

[Like a good short story] it feels both intimate and expansive to me. It was funny you used the term “Sadinista!” to describe it in the recent [NY] Times interview.

(Laughs) Everybody gets mad when I call my music sad. My kids, especially, don’t think it’s sad. I just think it’s kind of a common trope for the kind of music I make, you know?

I saw that and thought, “Oh somebody’s definitely doing a dub remix of this album.”

Oh, I hope so, I would love that!

Another of my favorite songs on here has a fascinating story behind it that I had never heard before. The arm of “Amar Bharati.” Could you tell our readers about his unusual story?

Yeah, there’s this guy who is an Indian ascetic. I don’t know if I’m pronouncing that word correctly. In 1973, he put his arm in the air to promote world peace, as a resistance to war. He said he would take his arm down when there’s world peace … and as far as I know he’s still alive. And now I don’t think his arm can come down.

Right, the muscles have atrophied. I saw the photo … 

Which is really a wild, kind of profound concept. I don’t really write that many songs specifically about a topic like that. I think that’s an example of something that the triple record gives you space for. A song like that might be too out of place and incongruous in a shorter record. But when it’s surrounded by other twists and turns and other different types of genres, I think it makes more sense.

You’re playing a different venue this time in Richmond: Lewis Ginter Botanical Gardens, a lovely place with flowers everywhere. It made me think of an old interview I did with Ian MacKaye, when his band The Evens played here. He was talking about how he prefers nontraditional venues. Music is sacred to him, it predates language. He wasn’t bellyaching about bars, it was more that music is so essential that he felt it should be presented anywhere. How important is setting to you when playing live and trying to achieve a sense of community?

I mean, I think it’s more important than ever. It feels more important.

Wilco has toured a lot in the last five years, since the pandemic, as the audiences have become more and more comfortable being out in public again. Early on, it was pretty sketchy. People were having a tough time just being present, you know? Because they were a little scared. Now it just feels like people are kind of basking in it, as being this unique thing that they’re glad it still exists (laughs). You know? There’s some added value to it. Maybe Wilco has just been around long enough that people are starting to come around to it in that way, but I don’t think so. I think it really is important to feel that connection – that communal congregation.

Those early days of the pandemic feel so long ago. I remember being alone during early lockdown when people were most freaked, and sitting right here, playing guitar along to these live streaming sets that Richard Thompson and Michael Hurley were doing from home. Being able to play music really kept me company. Did you start writing some of [“Twilight”] during the pandemic? When did the floodgates open?

Well, it’s always hard … everything gets kind of mixed up. When you write a lot, you tend to forget things you’ve written. And I like that, because I like to go back and be reminded of things and come at them with a little bit of objectivity and just go, “Wow, I really like that, or I don’t remember doing that.” That’s sort of one of the processes of choosing material, you get to respond to stuff.

“Lou Reed Was My Babysitter” was written definitely during the lockdown period in COVID. But a lot of this material was written for this record, and specifically for this band and their voices. Singing with my children, singing with Macie [Stewart] and Sima [Cunningham] and Liam [Kazar], and the way that we sound when we sing together, which we’ve done a lot of. This is mostly the people that have been going out with me and playing shows for the past solo records.

When you’re writing for your solo records, does it tend to be more personal?

Not necessarily. I think some of the subject matter can be the same. I think there is something psychologically different about attaching a band identity to something. I’m starting to maybe figure out that there’s just an intuition that is more based on what kind of weight a song can withstand, band-wise, you know?

Wilco is a six-piece and you want to make the most of those six pieces. A lot of times when I hear a song, I don’t necessarily hear that, and that seems like those are the songs that end up on my solo records. You know, maybe I don’t feel like this song is going to be able to handle (laughs) making place for all these different elements that you don’t necessarily want in every song. Wilco is good about that, too. We do stripped-down and are able to make six pieces sound like something simpler. But it takes effort. And sometimes, I think it’s just my intuition that the song can live by itself without that.

That Lou Reed tune is one of the more rockin’ songs on here. I remember thinking, if that was my song I’d have to call it, “Lou Reed used to buy his pickups from my ex-girlfriend’s mom.” She worked for Lindy Fralin here locally, who does those hand-wound pickups. 

(Laughs) Oh yea, I know him. Wow.

I think one of the best sections on your record, or one of my favorites that is, is the “Mirror” “Secret Door” “Betrayed” “Sign of Life” section. They all hit right in a row. Do you think any of these songs will change much in the live setting, either arrangements or vocally?

Not really. “Mirror” is going to be a challenge to perform live, because it’s so warped with ring modulating basses, you know? That was done in the studio, me and Spencer, that’s not quite a full band kind of performance on that.

“Secret Door” though is, that’s pretty much a band sound.

“Secret Door” almost has a little Irish jig motif in it, near the bridge. 

Yeah, that’s in 13 [time signature], apparently. I only found that out because [Wilco drummer] Glen [Kotche] stopped by the studio and said, “Wow, you have a song in 13.” (Laughs).

The whole album really was recorded beautifully. The way the drums sound on “New Orleans” reminded me of Mo [Tucker]. Did you have a specific philosophy in mind with the recording?

Absolutely. One of the things that seemed really important, philosophically important: I want to make records that sound like people. You can hear hands. You can hear faces. You know what I mean?

For sure. Merle Haggard once told me that he didn’t love digital recording because it “takes away the breath beneath my words.” Too cleaned up, I guess.

Yeah, totally. Absolutely. I mean, I don’t care how you record something as long as it feels like something that happened. Even the weirder things, I feel like I should be able to close my eyes and think of people in a room — and I get to be there. The space is really important to me, to feel like the listener can kind of project themselves inside of it.

A lot of recordings are really flat and don’t allow that. I think there are some amazing recordings that are super amped and compressed, pop songs that squirt out of the speakers, and that can be super cool in that environment. But that’s not me, that’s not the kind of records I want to make.

I think as AI gets more and more prominent, and the way things are going, I think that we should probably be aiming towards embracing more mistakes and embracing the feeling of a group of people making mistakes together. Which to me, makes it exponentially harder to replicate.

I’m a few years behind you in age. But it’s weird to reconcile the fact that “I guess I don’t get to see how the movie ends with humans.” Will they survive AI?? Global warming? Tune in next … annnnd it looks like we’re out of time on this Zoom. Hey, thanks. Nice to meet you, I’ve enjoyed your music for many years. Hope you get to stop and smell the flowers in Richmond.

Thanks, Brent. Nice to meet you, too.

Groovin’ in the Garden presents Jeff Tweedy with support from Liam Kezar on Saturday, Oct. 25 at Lewis Ginter Botanical Gardens. 7 p.m.