The Most Gut-Wrenching Jason Isbell Songs (With Guest Commentary by Jason Isbell)

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Next month, Jason Isbell will release his fifth solo album, Something More Than Free. In his genre — he’s grouped into that vague, amorphous zone between rock, folk, and country known as Americana — Isbell is regarded by many as the best lyricist in the game. His forte is affecting story songs about authentically flesh-and-blood characters from flyover country; when Isbell, 36, writes about barflies, low-income service-industry drones, and struggling parents who themselves are barely out of adolescence, he gives otherwise invisible people agency. Isbell’s very best tunes will seize your heart and empty the oxygen out of your lungs.

Something More Than Free builds on the gains made on Isbell’s previous LP, 2013’s Southeastern, a personal watershed that benefited from his recent sobriety. Unlike the moody, riff-centric work he produced with his former band Drive-By Truckers, Free is largely acoustic and nuanced, reflecting on the gains that Isbell has made in his personal life and the familial bonds that saved him from the brink. It may also make you blubber like a Friday Night Lights marathon would.

Recently, I decided to rank my top 10 most gut-wrenching Jason Isbell songs, and then asked Isbell to talk about each track and his songwriting process.

10. “Speed Trap Town” (from 2015’s Something More Than Free)

This is one of my favorite songs on the new record. I love how it starts in the middle of the story — it takes place in a grocery store, and the first line goes, “She said, ‘It’s none of my business, but it breaks my heart’ / I dropped a dozen cheap roses in my shopping cart.” You’ve used this narrative device in other songs and I’m curious: Do you know in your mind what the larger story is, and what you’re leaving out?

You know, usually there is a larger story in my head but I think that a lot of those details aren’t necessary. [In] a song, you have such a little amount of space to work with. And it’s really hard to tell a story unless it’s just the right, most pertinent details. But I like when songs do that — there’s a Ben Howard song from his record last year, where the first line is “Oh hey, I wasn’t listening.” I love that. Somebody’s trying to talk to him but he wasn’t paying attention.

You’ve said you do a lot more editing now than you once did. 

I think that’s the way that I write now. I don’t go by just an immediate inspiration kind of thing. The older I get and the more I practice, the more I realize it really helps if you do as much work as possible. I own the record label now, so I don’t have to follow a record every eight or nine months. I can take my time and work. When you stop drinking, that comes in handy, ’cause I can spend eight or nine hours on a song without feeling the need to go out and get drunk and shoot pool.

9. “Songs That She Sang in the Shower” (from 2013’s Southeastern)

This is another song that starts in the middle of a scene. But I wanted to ask you about another bit of songwriting minutia — I’m a fan of songs that reference other songs, as this one does. Is there a reason you chose songs like Dusty Springfield’s “Breakfast in Bed” and Pink Floyd’s “Wish You Were Here”? Do they have special significance or did they just fit the rhyme scheme?

Well, I had a lot of options for that one. And a lot of them didn’t work with the meter and the phrasing. But the ones that I ended up choosing I thought were best at reflecting the character that I was describing.

Most of the people that I spend my time around are people who listen to a whole lot of different kinds of music. And I think that’s the person I was trying to create in that song. That’s a good reason for missing somebody when the relationship is over.

8. “The Devil Is My Running Mate” (from 2007’s Sirens of the Ditch)

I hadn’t even thought about that song in a long time. It’s a political song, obviously.

I picked it because it’s so overtly angry, which is unusual for you. Your songs are usually implicitly political, in that you write about people who are just trying to get by, as opposed to sloganeering.

I think politics are a very personal thing. And those stories are reflective of a bigger truth. I try to make statements that aren’t broad because that doesn’t make for good writing. I don’t get commentary as my job, because I’m not very good at that. The way I do it is by writing songs, and I have to be small, I have to make the stories a bit personal. But, you know, the middle class is disappearing and it’s all but gone at this point, and it’s going to get worse before it gets better.

7. “Daisy Mae” (from 2011’s Here We Rest)

At some point I started to realize how many people I knew had suffered some kind of sexual abuse when they were young. It wasn’t talked about a whole lot, but the older I got, after relationships with a few different women, I realized that it’s almost everybody, honestly. I thought about that for a long time. I just tried to put myself in the shoes of somebody who was in that kind of relationship, somebody who was struggling with a partner who really had those problems in childhood. Really, it’s pretty amazing what percentage of boys and girls have had to deal with that kind of thing when they were young. It just shocked me when I found out.

6. “Children of Children” (from Something More Than Free)

There’s a running theme in your songs about generations — kids and parents, and how your perspective on that dynamic changes as you get older. You return to that in “Children of Children.” What inspired this song specifically?

My wife and I both grew up with parents who were very young. Her mom was, I think, 17 or 18 when she was born; my mom was 15 when I was born. So, as we got older we started thinking a lot about that — about the time that those people missed because we came along when we did and because they devoted so much of their lives to taking care of us.

Why does that shifting generational perspective interest you as a songwriter?

Well, those are the people who I’m closest to. I try to write what I know. It’s always an interesting relationship, especially coming from the South — you know, we’re close to our families. I came from a long line of people who depended on their parents to survive, and parents who even depended on their children to survive. The older you get, the more you see your parents as human people, you start to understand their flaws and the things that make up their character. I think that’s when you really start becoming an adult yourself, when you can see your parents as human beings rather than some sort of deities.

5. “Outfit” (from Drive-By Truckers’ 2003 album, Decoration Day)

That generational theme is probably best expressed in “Outfit.” Did your father give you that advice in real life?

Well, it was all inspired by that. He didn’t say everything exactly that way. Some of those lines were pet peeves of his, some of them I was trying to capture his sense of humor. But it’s pretty close. I mean, each line in that chorus and each line in that song is pretty directly related to something my father and I had discussed when I was growing up.

Was there anything in particular that he wanted you to learn?

The stuff about making sure to call home and keep in contact with my sister. That I think was number one for him. Sometimes when you don’t have anybody else to depend on, you’ll have those people who you’re either blood-related to or the people who you’ve accepted as your family.

4. “Cover Me Up” (from Southeastern)

This song cinched a spot in the top five when I read that you made yourself choke up the first time you played it for your wife, Amanda Shires. 

Yeah, the first 20 or 30 times probably.

It is the purest love song in your catalogue. Is it harder for you to be vulnerable and happy in a song than it is to talk about the darkness in your life?

It’s not easy. You don’t look real cool when you’re writing a song like that. It’s hard to keep up a James Dean type of facade if you’re thanking somebody for your salvation. But when you’re writing the kinds of songs that I do, I think your job is to try to be as honest as you possibly can and write about those things that make you uncomfortable sometimes.

I had gone to a wedding — a friend of mine who used to work for us had gotten married. He was not a professional musician or a songwriter or anything like that, but he had written a song for his wife and played it at the wedding, and I could tell how incredibly difficult it was for him. Even though it wasn’t a great song by the standards that we’d normally categorize great songs, for the purpose it was perfect.

That seems like the hardest thing to do, to write a song specifically for a man or woman and then sit down and sing it at the end of the day. And that’s what I tried to do. We weren’t married yet, so I guess it worked out all right.

She could’ve told you to take a hike if the song sucked. 

Right. She’s pretty picky about songs, so I think I would’ve been in trouble.

3. “Danko/Manuel” (from Drive-By Truckers’ 2004 album, The Dirty South)

I was reading This Wheel’s on Fire, the Levon Helm book about his time with The Band. He talks about how they had this pact on the road — it was kind of a joke —that whoever died first, they would take his body, take him home, and bury him and all of that. And that stuck with me, juxtaposed with the scene of Richard (Manuel) being found in a hotel room when they were at their lowest point, when they weren’t making a lot of money or doing a lot creatively, and Richard ended up killing himself. I thought about that and it really moved me, especially considering that I was traveling around with a band at the time and we were having some problems — problems with addiction and depression, and trying to stay relevant and get relevant in the first place. I saw a lot of myself in that book.

When you were younger, did you have a romantic notion of that sort of self-destructive touring-musician archetype?

I don’t know if I ever thought of it that way, because I saw the reality of it from the start. I guess I romanticized it as an excuse to keep going, and keep growing, and keep living that way myself.

My outlook on it hasn’t really changed. I mean, I knew at the time that it was [bad] and I just got real, real tired, to the point where I just didn’t want to feel like hell all the time.

2. “Goddamn Lonely Love” (from The Dirty South)

Most songwriters would be proud to call this their no. 1 gut-wrencher. For you, “Goddamn Lonely Love” is the runner-up. This song is evocative of a very specific feeling of being alone, drunk, and haunted by the past in a bar. Since you no longer get drunk or hang out in bars, can you still connect to this song in the same way?

I mean, I can still put myself in the places I was in when I wrote it, because it really seems like everything has gone by so quickly to me. I wrote that song about 10 years ago, I guess. In hindsight, it feels like it’s been 10 months.

When I think back to when I wrote that song, it’s pretty clear. And that helps me in songwriting, because you can’t always write about the place that you’re currently in. When I’m onstage, I often feel some of the same feelings — not necessarily as intensely as I felt them 10 years ago, but they’re still there.

1. “Elephant” (from Southeastern)

I recently dubbed this the saddest song of the millennium. I often try to avoid “Elephant” when I play Southeastern because I know it will take me out of commission for the rest of the day. How did you avoid the usual pitfalls of a song like this? Because there are a lot of smarmy, sentimental country songs about cancer.

Well, I didn’t want to write about cancer as much as the relationship. I think that that’s a big part of that song. Because there’s not a whole lot that can be said about cancer. But there are infinite details about human relationships. So, you focus more on that than the illness.

When you write a tearjerker like “Elephant,” do you know right away how powerful it is? Or is it like being a comedian, where you have to get in front of an audience to know if it works?

Sometimes that’s the case. But not with that song. When that song was done, I knew that the knife was going to be twisted.

It seems like the more I do this, the more able I am to separate myself from the creation of the song. When I finish one, I can listen to it with outside ears a little bit easier than I used to. And I don’t know why that is. Maybe it’s because I’ve written a lot of songs now.

With that song in particular, I wrote it in a hotel room on my night off, and when it was done I knew that I had done something that was really heavy. The only way I could explain that, really, is in the same way you know when you hear a song that somebody else wrote and it affects you like that. It affected me separate from the creation of it.

Filed Under: Music, Jason Isbell, Drive-By Truckers, Southeastern

Steven Hyden is a staff writer for Grantland. His first book, Your Favorite Band is Killing Me, will be released in May.

Archive @ Steven_Hyden