JON DEE GRAHAM performs two of his best songs, “Laredo” and “Big Sweet Life,” at nearly every live show he does. The first is a nightmarish tale of a man driving a blood-stained car to the Tex-Mex border and trying to keep that “small dark something” at bay by shooting heroin in a budget motel. The second is an uplifting hymn to reality in all its messy splendor, described by the singer as far more complicated and rewarding than any dreams, fears or plans inside one’s head.

Graham, a hulking baby boomer in a thrift-store plaid shirt and a porkpie hat, performs both songs with the same full-throttle commitment in his raspy baritone vocals and rude, noisy guitar riffs. This rock ’n’ roller, who grew up in the Rio Grande Valley and who has lived in Austin for decades, can tackle both songs in the same show, because he’s interested in the full spectrum of human experience, from its bleakest worst to its brightest best. He has both the emotional breadth to cover that spectrum and the writing and performing chops to carry his audience along with him. They’ll often sing along to both tunes.

In a sense, his willingness to dig into the muddy hole of “Laredo” gives him permission to be open-heartedly sentimental on “Big Sweet Life.” Similarly, his willingness to preach hope on “Big Sweet Life” allows him to be brutally honest on “Laredo.” He couldn’t pull off one without the other.

Graham was the guitarist in the Skunks when the band pioneered Austin punk rock in the ’70s, and he was the third guitarist-singer alongside Alejandro and Javier Escovedo in Austin’s roots-rock wonders, the True Believers, in the ‘80s. He was a longtime member, with Stephen Bruton and Scrappy Jud Newcomb, of Austin’s favorite Sunday-night entertainers, the Resentments, and one-third of the short-lived Hobart Brothers and Lil’ Sis with Freedy Johnston and Susan Cowsill.

But his greatest work has emerged on his solo recordings, beginning with 1997’s Escape from Monster Island and continuing through studio albums, live albums, EPs, anthologies and the soundtrack from the documentary film about him, Swept Away. Every one of those records juxtaposes songs of dark despair next to songs of unstifled optimism. What’s striking about his latest recording, this fall’s five-song EP Knoxville Skyline, is the way the two moods often coexist in the same song.

I recently talked with Graham as he drank his morning coffee at home in Austin.

How can you sing “Laredo” and “Big Sweet Life” in the same set, just a few minutes apart?

Anybody who pays attention knows the world is made up of contradictions and opposites. We live in a complex world, and we lead complex lives of both darkness and light. To me the sign of someone who’s truly awake is someone who can keep both of those things in their mind. When I’m happiest with my work, I’m able to do both of those in the same song, like “Careless Prayer” on the new record. The first verse describes the narrator’s drunken descent into darkness; the second verse describes the third ring of hell; then there’s a short bridge that introduces the mystery of prayer; and the last verse has the narrator on his porch with his family inside, growing his garden. So in that song, I get both “Laredo” and “Big Sweet Life” in there.

That’s also true of “Shoeshine Charlie” on the new record. It’s a roll call of people who’ve died or disappeared. There’s a real sense of loss but also a real sense of affection for those people.

When I introduce that song from the stage, I say, “This song is not about Shoeshine Charlie; it’s about change. You young people think things will never change, but they will.” It’s about all those people who hung out at the Continental Club in Austin in the ’90s. The line about El Nino going to find his biological family is true. He was my original drummer. When he first heard the song, he was bawling, not because he was mentioned, but because it was about a time that’s gone. It’s a song about appreciating what’s going on now, because it’s not always going to be this way.

Who was Shoeshine Charlie?

He had a shoeshine booth at the Continental and carried a snub-nosed .38 in his back pocket that he called Shorty. He took it upon himself to be the emcee and introduce the bands, but he never got the names right. He once introduced Alejandro’s band Buick MacKane as Buck McQuade featuring Hondo Escalator and his brother Harvey. When he died 10 years ago or so, there was an incredible turnout for the service. At the gravesite, as they were dropping him in, Bobby Rock and I played “Big Sweet Life.” I realized that all the songs about the cold, cold ground are true. The ground is cold. When it comes to change, death has the last word.

The Continental Club has been crucial to your career. You still play there every Wednesday and Sunday night.

When I first came back to Austin in 1995, Wednesday night was Musician Night at the Continental Club: if you were a musician, you got in for free. So it was packed on Wednesdays with all these musicians and strange characters. Even today it’s an audience that demands a lot but also allows you to take risks. My band the Fighting Cocks doesn’t ever rehearse. We’ll just talk through the chord changes and the arrangement before we go on. That’s how we work up new songs. It’s a high-wire act, but that’s how I know if a song is working or not. All of a sudden, you know the audience is getting it; it’s you and them together.

And what if it’s not connecting?

Sometimes there’s no connection. That’s a song we take out of the showroom and put up on the rack to look at it. Maybe I see a minor design error I can fix. Or I go, “Oh, it’s a piece of crap. That’s the problem.” Or sometimes, I’ll just be fooling around, and a good song will grow out of that. “Dan Stuart’s Blues,” on the new record, started out as a joke; I’d make up different lyrics every time we played it. Then one night the stories fell into place, and I said, “Oh, this is a real song.”

You sang Dan Stuart’s “Dreaming of Muhammad Ali” in your set for years.

Ali gave so much to so many people, so audiences respond to that song. Dan was at the Continental one night when I did it, and he had tears running down his face. Here was a song he’d written 15 years earlier, and people were still moved by it. There are so many amazing American songwriters people don’t know about, and Danny is one of them. He disappeared into Oaxaca for two years, but he was an expat even when he was here. His band Green on Red would sell out shows in Europe, then they’d come home and not be able to get a gig.

Your earlier songs were autobiographical, but on this new record you’re writing a lot about other people: not just Shoeshine Charlie and Dan Stuart but also Steve Silbas and Barbara Wolfe, who ran the Casbeers music venue in San Antonio.

These songs aren’t about how Jon Dee is feeling. I’m standing aside and looking at these people. It’s not like Randy Newman, who creates people who never existed doing things that never happened. It’s more that I’m describing people I’ve known. It’s working muscles I didn’t know I had. It’s unlike anything I’ve done before. You’d think it might be easier, because the scenes and words are outside you, and all you have to do is write them down, but they still have to go through your filter.

But that’s always been the unusual thing about your work: even though you came out of Austin’s punk rock scene, you were always interested in more literate songwriters.

I was lucky enough to be friends with people in college who weren’t listening just to punk. So I got to hear Randy Newman, Ry Cooder and Little Feat. When I heard Tom Waits, it was all over. He took apart everything we thought we knew about songs. When I heard Rain Dogs, my mind was thoroughly blown. With a lot of songwriters, I said, “I could have written that.” When I heard Tom Waits, I said, “I couldn’t have written that in a million years.”

When you were a sophomore at the University of Texas, your band the Skunks opened for the Clash at the Armadillo World Headquarters. What was that like?

There was an after-party that night at the Continental, and I ended up on stage jamming with Mick Jones of the Clash. I was up all night, then I grabbed my books and went to this big lecture class, and I realized, “I don’t belong here.” I left the class, went directly to the bursar and withdrew from college. But I was lucky to be in Austin, where it was hard to hide out in your own scene. As much as I loved punk, I couldn’t help but be influenced by all the other music in town. Between the Skunks’ set and the Clash’s set at the Armadillo, I looked out at the sea of people in the audience, and there were cowboy hats, ponytails and mohawks. That was Austin in a nutshell. Whether it was Alejandro [Escovedo], Stevie Ray or Joe Ely, we were all brothers.

You’re trying some new things on this record: B-3 organ, even female vocals.

I’ve done the live rock ’n’ roll album where you go in and just cut it. I’ve done the meticulously assembled record in L.A. with Jim Keltner. This was a record where I did just what I wanted to do. I’ve always wanted to make a record that was simple in a big room with a big sound. I’ve always wanted to make a record with female vocals. I knew the beauty-and-the-beast contrast between these heavenly voices and my death rattle would broaden how people hear the songs. As for the organ, I was shooting for this 1975 drunken Mexican lounge band feel. We sent the track off to Michael Ramos, who’d been the keyboardist in my Austin band the Lift, and he nailed it so beautifully it was as if he were wearing a plastic wig.

Why did you want to change things up?

Sometimes I feel like I’m playing the Jon Dee persona, the rough-and-tumble character, the punk-rocker with a folk-music sensibility. I’m not saying I’m not all those things, but I want the freedom to also be jaunty. It’s the same thing we started this conversation with: life is enormously complicated, and part of that complication is that life is often funny. But I’m supposed to be the sensitive songwriter with the loud, scary guitars. The hell with that. It’s a relief to sing something funny like “Dan Stuart’s Blues,” something that’s not meant to scare you or confuse you.

What kind of music did you grow up on?

At home we listened to hard country. On the radio, I listened to KISS and KMAC in San Antonio, hard-rock stations that also played the Sex Pistols. When we went to dances in high school, it was always with a Mexican horn band. But I did what everyone does: I denied my old music and said the rock of my generation was the only music. Then I looked up at 40, and said, “Oh, the whole Latin-soul thing is a big part of who I am.” It’s an essential phase — to throw out everything your parents liked. But we’re throwing out empty boxes, because that stuff stays inside us. By my second record, every other song was a musical homage to the Latin-soul stuff and a lyrical homage to the country stuff.

The hard-edged rock ’n’ roll is in there too. But you seem determined to strip away all the illusions about the rock ’n’ roll lifestyle. A song like “Beautifully Broken” is pretty ruthless about deglamorizing drugs and alcohol.

I had a talk with Alejandro one time about the beautiful losers. We were talking about choices he and I had made. There was this culture that said that self-destruction brought you closer to the truth. We finally learned that’s bullshit. I read once that Lou Reed said that self-destruction is a beautiful thing until you achieve it. I saw Townes Van Zandt twice. Once he was the best songwriter I’d seen in my life. The second time I couldn’t believe I’d paid good money to watch him play three songs and fall off a barstool. The myth is a lie.

How did you put that myth behind you?

Stephen Bruton and I were talking about drugs and alcohol once, and he said, “Jon Dee, you wrote those songs in spite of the drugs and alcohol, not because of the drugs and alcohol.” I reached a point where I wasn’t physically or mentally able to create. I had to choose one or the other: drugs or creativity. I knew the drugs always wear off, but creativity doesn’t.

Originally published in Fall 2016, No. 68