Although Jason Isbell has been around a few roots music blocks over the past 15 or so years — as both a member of the Drive-By Truckers and a solo artist — it was his 2013 album, Southeastern, that brought him truly widespread acclaim. The song cycle emerged after Isbell went to rehab for his alcohol addiction. And it’s a doozy … an Americana Award-winning, critically acclaimed doozy.
Having set the artistic bar so immeasurably high, Isbell challenged himself to best that effort with his new LP, Something More Than Free, and both he and producer Dave Cobb believe he did. It’s another doozy, to be sure. But it’s so different from Southeastern in both form and function that comparing the two feels like a musical Sophie’s choice. Though the sparse and poetic considerations have been displaced by wide-eyed, yet surgical explorations, both albums showcase an artist with an inimitable, indelible gift.
Now that you have a couple post-sobriety years under your belt, what things are better, what aren’t?
Everything’s better. I get along with folks a lot better. I make a lot more money and it doesn’t all go down my throat, or up my nose, or anything like that. I just generally feel better. I have more time to work. I have a family now — a wife and she’s having a baby pretty soon. I like those things. I come from a place where those things are highly valued. And the older I get the more I go back to those values. And I don’t mean values as far as moral values; I mean things that you really care about. I care about having a family and taking care of them, so I feel much more satisfied in that realm.
Do you feel like, in a certain spiritual sense, you had to go through all of that and get sober so that Southeastern and everything that follows could be made? Because if you did anything differently …
It wouldn’t be the same. I might be happy, but I would not want to roll those dice. [Laughs] I don’t regret anything, really. The few things that I realized were bad decisions at the time, there’s no way to calculate how different my life would be right now had I not made those terrible decisions when I did. So I can’t complain about that. I can’t look back and feel regretful about that. I do have some remorse that probably won’t ever go away completely just because of the way I treated folks at some points in time. But you can apologize and try to do better and move on.
It seems like having folks know so much about your life makes for a more authentic and true connection with your fans, yeah?
I think so. I’m not shooting for the average. I’ve never really tried to get the most fans possible out of making music. There are a lot of people who are very good at that. I’m just not one of them. I think there are plenty of people on the fringes for me to have a good, long career and still wind up around people who remind me of myself in some ways.
When you played the Ryman last Fall, I was struck by people raising their glasses to your sobriety when you sang “swore off that stuff” in “Cover Me Up.” They seemed genuinely supportive although completely unaware of the irony.
I think they may have been aware of the irony … some of them, at least. I like to think that they are. But being a hypocrite doesn’t make you wrong. It doesn’t make your beliefs wrong. It might make your behavior wrong, but it doesn’t make your beliefs wrong. And they’re rooting for me. A lot of those people aren’t alcoholics and it’s very, very different for an alcoholic to hold up his beer for somebody who’s not. The world needs wine. The world needs raisins. If people can have two drinks and then stop, then I’m all for it. I think they should do that as often as possible. But they’re cheering for me because that record would not have happened, and those moments would not have happened, if I hadn’t quit drinking. So I think they’re happy that they can be in that period with us.

I don’t know if you were upset by Southeastern not getting any Grammy nominations. But, did the Americana Music Award wins make up for the Grammy snub?
I see them as completely different things. The Grammy Awards are for people who have different jobs. The Grammys do give out an Americana award and folk music awards. But, very often, people look at the category and they see a name that they recognize and that’s who they vote for. I get a ballot. I know how that works. They see, like … I think Ziggy Marley’s won every reggae Grammy for the last I don’t know how many years because his last name’s Marley. Nobody’s listened to that record who’s voting on it. They just see Marley, so they check that box. I know that. I know how that works. So, no, it didn’t offend me. If I ever win one, I’ll be very grateful for it, but …
It hurt my manager’s feelings and my wife’s feelings and my accountant’s feelings more than it did mine. They were all backstage when we came off stage that night and they’d announced the nominees.
[Laughs] So you got to be pissed by proxy …
[Laughs] Yeah. It’s great to have people pissed off on your behalf. It really is.
For this new album and the last, you didn’t play anyone the songs before you went into the studio, so you must have a huge amount of faith in and respect for your team. How does that factor into things for you? Does it free you up psychologically?
That’s a production technique, as much as anything else. It’s a luxury to be able to do that because, if we couldn’t afford three-and-a-half weeks in the studio, we’d have to work things up on the road or in rehearsals. Everybody would have to get work tapes and demos and all those things, and then we’d have to go in and cut it in a few days. But, luckily, we could go in and take the time. People in the band are fast. They’re good listeners. They’re great players. Dave [Cobb] is fast and his instincts are incredible. Usually the first idea that he comes up with winds up being a really great idea for the song. I knew that going in and I have my own label for putting the record out, so I didn’t have anybody to answer to, really. So it was a nice thing to be able to do.
When you go in and you’ve worked songs up on the road, people have to unlearn parts and that can be really trying sometimes because you fall in love with those things, you refine them over the course of a few shows or a few months. You fall in love with the parts you’re playing and you have to be talked out of that and talked into playing what’s better for the song. If my band wasn’t as good as they were, it wouldn’t be possible. If Dave and Matt, the engineer, didn’t work as well as they do, it wouldn’t be possible, but I like being able to do it that way.

What’s the best song you’ve ever written?
The most recent one. [Laughs] I told somebody recently, songs are like children — you always like the youngest one best.
How about the top three?
I could tell you the ones that have had the biggest impact on people, but I don’t necessarily know if those are the best. I think “Travelin’ Alone” is a really, really strong song because I don’t think any of the words are unnecessary. I think the bridge is the perfect amount of going in a different direction and staying on the same path, sonically and lyrically. And that’s not something that’s easy to do. A lot of people either don’t write a bridge, these days, or they write one because they feel like they are obligated to and it’s not adding anything to the song. But I feel like that one is really strong as far as the craft of writing a song goes and the art of communicating.
“Dress Blues” is a strong song, but that’s for different reasons. I think that’s because I was telling a story rather unadorned and able to tell that story without putting too much of my own character in there. And “Elephant,” I think, is one that every night when I sing it, it feels like I’m singing a good song because I want to tear up sometimes in that song. So, if it affects me in that way after singing it a thousand times, I must have done something right. I like the relationship in that song. I like the fact that it’s not a love song — it is, but it’s not a romantic love song. It’s written between two friends, a man and a woman who are close in different ways and depending on each other for different things. I think I picked the right details in that song.
That one knocks me down every time.
Yeah. It’s got something to it that’s a little bit bigger than me, I think.