Robert Earl Keen is a legend of Texas-style outlaw country, with ties that go deep in the state: He was born in Houston, educated in College Station, is based in the Hill Country, and has traveled to every corner of Texas in his 30-year career. His 11 studio albums and six live albums—produced on venerable record labels, ranging from the Americana-based ones like Sugar Hill, New West, and Lost Highway to mainstream ones like Arista and Koch/E1—show imprints of his lifelong love affair with bluegrass music. But he’s never fully committed himself to the genre. 

That changes in February, when Keen will release his first proper bluegrass album, Happy Prisoner on Dualtone Records (current home of hotshot country-tinged acts like the Lumineers and Shovels and Rope). Produced by longtime Robert Earl Keen collaborator Lloyd Maines, Keen supplemented his traditional band on Happy Prisoner with guest spots from Lyle Lovett, Natalie Maines, Sara Watkins (Nickel Creek), Danny Barnes (the Bad Livers), and Kym Warner (the Greencards) to put out the album he’s wanted to make his whole career. In this exclusive Q&A Texas Monthly talked to Keen about building a musical canon, why now was the time to go full-on bluegrass, and why, when you’re doing something at the right time, the whole world seems to come together for you. 

Your history with bluegrass music is pretty well-documented, if you listen to “The Bluegrass Widow,” but that song was a long time ago. What made you decide to do this album now?  

It was one of those points where you just say, “If I don’t do this now, I won’t do it.” I had given it a lot of thought and felt like it was the right time. I had put out a lot of records and written a lot of songs. My initial fear was always that somebody would think that I would run out of songs or things to say, and so I didn’t want to muddy the waters with that kind of thinking—but at the same time, I always felt like this was something that was in my nature to do. It came to that point I thought, “You know, I gotta quit worrying about what people think about this. I’m just going to do it,” so I did it.

How did you choose the songs to put on this record?

I chose songs that I loved from years and years back, all the way from things like “Poor Ellen Smith.” I always thought that was a great, great murder ballad in that way that there was much more remorse in it, than there was just cold, hard scary stuff than they do in, like, “Knoxville Girl.” It’s just almost sociopathic murder in that. I felt like that was really a beautiful, sad song and I’ve known that song forever. Almost all the songs on there are songs that come from the earliest part of my musical education. “T for Texas,” I know is not considered a standard bluegrass number, but I listened to Jimmie Rodgers when I was, I don’t know, 13, 14 years old, just non-stop. I just had the record going 24 hours a day. I’d go to sleep to it, so those kind of things, they’re part of my makeup at this point. When I think of music that I like and I’ve always liked and music that I think has some timelessness to it.

Is getting to put “T For Texas” in the same context as something like “Long Black Veil” a chance for you to create your own canon?

Those are definitely the kind of songs I’m drawn to. Narrative songs are, by and large, what I write, and it’s also what I’m always interested in when I listen to music. I love a narrative. I’ve become someone who likes a great emotional song, but in general the narrative is what I stick with, and bluegrass is almost exclusively a narrative. You meet the girl and the girl leaves you or you leave the girl. You leave your parents and you come back to your home, you know, real basic human needs. That was what I was going for. I didn’t really have a plan so much. I just had a lot of songs that I really loved, that I thought that I could do justice to. When I pick songs, whether it’s for this bluegrass record or outside songs that I’ve done on other records, I always go for the songs that I truly feel like I can present, that when I sing these songs, I see the pictures in my head. I’m able to put that emotional feeling in the song that I get from my own rendering of what’s going on within the story.  

How does that work when you do a collaboration? You sing “T For Texas” with Lyle Lovett, and “Wayfaring Stranger” with Natalie Maines, on this record. When you approach those people, do you think, “I hear this song with this voice on it?”

Yeah, absolutely. Exactly. With Lyle, I know that he has some of the same feelings about some of the older material, some of the more simple material, simple country music or bluegrass music. Lyle, although he doesn’t talk about it as much as I do, he has a really a pretty vast knowledge of bluegrass music, and I’ve heard him play some really great bluegrass songs within his own band and with other people. He’s a great singer and a great deliverer of the songs, so “T for Texas” just seemed like a perfect idea to have Lyle sing on it. Lyle and my relationship goes way back, but I’m always a little bit timid about asking him. Anyway, he was more than happy to. I didn’t even hardly finish the sentence and he says “Yes, I’ll do it. That sounds like a great idea.” I guess it was a great idea.

Was finding a common ground in this love of bluegrass music part of the fun of making the album?

Yeah, absolutely. The guy who played the banjo, Danny Barnes, is originally from Temple, Texas. He played in the Bad Livers, which for lack of a better term was a punk band. A punk acoustic band, which had really crazy sort of lyrics and a real odd setup, but very, very cool, and Danny is a musical godhead. His initial entry in this world of music was all bluegrass, and he’s probably the best bluegrass player you can ever find, but he doesn’t really play bluegrass because he’s so far out there musically. He made a record with Bill Frissell, and he plays with all kinds of crazy little string quartet things with his banjo. He has incredible knowledge, so when I asked him, “Look, Danny, just play these old bluegrass songs that you know,” the guy just stepped up there. I don’t think he missed a note, ever, in the whole time that he was playing. There’s always, “I don’t really hit that lick very well.  Can we do this again?” and you’d go, “You want to do this again, Danny?” and he’d go, “Sure.” He would just start playing it, and there were no outtakes from Danny Barnes. He knows it probably as well as anybody on the planet. I think he was so happy just to do something that was part of his initial love of music. He has one of my favorite stories about music: He said, “I remember seeing the Glen Campbell Goodtime Hour, and it started with this picture of a banjo, and then it opens up and there’s John Hartford playing, and when I saw that, it determined my entire economic future.” That’s how he started way back in the late 60’s—just being fixated on the banjo and the sound of the banjo. I don’t think there’s anyone, not just that plays as well, but loves the banjo as much as he does, so when he got the chance to just play the banjo in the most classical form he just ate it up.

Where did the title Happy Prisoner come from?

This is the same kind of thing I do when I make records: I go into it with just sort of a placeholder working title. And they say, “Hey, what’s the title?” I go, “Here’s what it is.” I think my initial title was Hard Lovin’ or something. It comes from East Virginia blues and then as I went along I kept thinking I know I’m going to come up with a title that I really like, since like I said, it was a placeholder. I should make up one of those Bob Dylan huge fabricated stories where it was something magnificent, but literally I was digging through my t-shirt drawer, and I pulled up this pair of pajamas I’d had that had horizontal stripes. They’re royal blue and grey horizontal stripes. When my family, my little family, my two daughters and my wife, we all bought these together and we used to wear them around and watch TV and we would call them “the happy prisoner” and I looked at those pajamas and I thought, “Happy prisoner.” That’s it. That’s what this record is. It’s Happy Prisoner, because I love bluegrass, and if you get locked into it, you’re kind of there all your life, but you’re always happy about it. That’s where that comes from.

Happy Prisoner is your first record for Dualtone. How did that come about?

I’ve known [Dualtone founder] Scott Robinson for, I don’t know, all the way back to the late 90’s. I worked with him at Arista when I was with Arista, and then I worked with him on some other things, just some side projects. I’ve always been friends with him and always had a really good relationship with him. That was another thing that just fell into my lap. He happened to be at SXSW. I had shored up most of the record at that time, and I just went over and said, “You know, I thought maybe you’d want to listen to it. I’m not even pitching you. I just thought you might like to see what I”m doing.” He called me and said, “I had no idea what you’d be getting into with bluegrass. Frankly, I had my doubts.” But he loved it from the very beginning, so everything for this record has had a nice shiny halo around it. Another thing, is the fact that I’ve known Peter Rowan who is truly a legendary bluegrass player for many, many years. I’ve written songs with Peter, played shows with Peter, and stuff like that, and he showed up at that studio totally at random. He was a friend of the guy who owned the studio, and happened to just come to see him, and so Peter was standing there and I say, “Hey, you gotta listen to this song. We did one of your songs. We did ‘Walls of Time.'” While he was sitting there listening to it, he picks up a guitar and this is totally Peter Rowan: He just always has some kind of instrument in his hand, and he starts telling this story about “Walls of Time,” how he wrote this with Bill Monroe. I said, “Hey, would you mind telling that on the microphone so we can get this down as a sort of an archival thing?” He said, “Yeah, sure.” So these things kept coming together with this record, and I truly believe it’s because of this whole feeling. One must do something.

So you were in the studio making a bluegrass record and Peter Rowan just shows up?

Just showed up. Like I said, I had some history with him. I wanted him to hear the song that we did, his song. I wanted to see what he thought of it, and then when he started telling the story I said, “Oh, man.  Will you tell that story?” We got him to tell a story and then I said, “Hey, I’ve already cleaned up this song pretty well, but I really needed a harmony on ’99 Years and 1 Dark Day'” and he said, “Oh, I love that song.” “You can sing it, right?” “I can sing anything.” Okay, great. So we just got him in there and he sang this great, real honking sort of hillbilly harmony to it. This worked out perfectly. We’ve had a lot of real good fortune. A lot of times, the good fortune is because you have some kind of great passion for a certain thing and things come together. I don’t want to be too cosmic about it, but I do have that belief.