We Asked Four Singers (and Ethan Hawke) Which Willie Nelson Songs They Love Most 

By early 1973, Willie Nelson had given up his Nashville dream of country stardom and, after flirting briefly with retirement, moved back to Texas and settled in Austin. At that point, the most likely outcome was that he’d play out his career as the local hero he’d always been. But, of course, he went on to become one of the most beloved entertainers in the world.

In 2020 Texas Monthly launched the One by Willie podcast to explore what his music means to his fans. On each episode, we talk with one notable Willie devotee, and, naturally, a lot of the conversation focuses on albums (all 147 of them!) and songs. Here, we excerpt a few of our favorite guests’ discussions about their favorite Willie tracks.

Steve Earle on “Local Memory,” from Shotgun Willie (1973)

There was no point while I was growing up that I didn’t know who Willie Nelson was. I literally went to high school four and a half miles from Floore’s Country Store in Helotes, and even before Willie moved back to Texas, he came to play there. My dad went to those shows. 

Then Shotgun Willie came out in 1973, when I was just on the edge of leaving home. “Local Memory” stood out because I was beginning to write songs that didn’t have a girl’s name as a title, and I had never noticed a country song that was literature the way that one was, intentionally. The “memory” was a character, like a poltergeist, a creature loose on the town and wreaking havoc. Cole Porter wrote like that [with lyrics that read like literature]. Porter probably could have become an academic and a poet, an American Seamus Heaney. But he liked musical theater, so that’s what he did, and he was kind of slumming. 

Willie’s like that. I’ve never heard a Willie Nelson song that wasn’t alliterated past the decimal point. He does it on purpose, and he was put here to do it. I really believe that.

Vince Gill on “Healing Hands of Time,” from The Sound in Your Mind (1976)

Just the song’s title, in itself, is intriguing. Like the way the first line of a great song—“He said ‘I’ll love you till I die’,” or “Yesterday, all my troubles seemed so far away,” or “Hello darkness, my old friend”—will make you go, “Okay, I’m in.” And Willie always wrote lyrics that were a little bit deeper than most people’s. His songs about hurting are still the blues, but “I’ll get over you by clinging to the healing hands of time. . .”? You can’t get any better than that. Truthfully.

“Healing Hands” is steeped in a spiritual place. I know from my experience with “Go Rest High on That Mountain”—which I wrote when I was grieving losing my big brother—that when people hurt the very most they’ll ever hurt, and they lean on your song, it’s the sweetest feeling you could hope for. It’s much more meaningful than a hit. Willie’s had several songs, like “Healing Hands” and “Family Bible,” that did that.

Margo Price on “Angel Flying Too Close to the Ground,” from Honeysuckle Rose (1980)

I found “Angel” in my early twenties, and it was one of those songs you have to stop and listen to a few times to really take it in. Who writes a melody like that? It’s so good, so haunting, with the most poetic, almost surreal lyrics. My favorite line is, “I patched up your broken wing and hung around a while / Trying to keep your spirits up and your fever down.” That line is so good it hurts.

It’s about losing someone, but there’s a lot of mythology behind who that might be. I’ve seen speculation that it was Connie [Willie’s third wife]. They were having trouble then. I’ve heard he dedicates it sometimes to Billy, his son who died in 1991. But Willie doesn’t explain every detail. He lets people find the meaning themselves. And having lost a child, I know that no one should have to outlive their children. So to me, it’s just a beautiful song about loss.

Ethan Hawke on “Too Sick to Pray,” from Spirit (1996)

“Too Sick to Pray” and the album it’s on, Spirit, came out a little before my daughter, our first child, was born, and we played it all through the pregnancy. It’s such a moment of transition. Yes, the baby is in a cocoonlike state, about to be a butterfly, but the parents are too. And for me, “Too Sick to Pray” captured that strange feeling when you turn your back on your spiritual life, when you’re too caught up in your own nonsense to remember your humility. So much of the best of Christianity is present in that song.

There was also a connection to Red Headed Stranger. When I was a kid and my parents divorced, my dad listened to Red Headed Stranger over and over. He had it on LP, on eight-track. He’d play it on the piano, and we’d sing it. That album was a real source of healing for him. So it made my heart feel so good, when I was 26 or so, to come across Spirit and have Willie in my life, just like when I was six or so. Only now I was getting ready to be a parent.

Kacey Musgraves on “Are You Sure,” from her album Pageant Material (2015)

I’m a night owl, and I get into YouTube wormholes. One night I stumbled upon a Willie demo from 1963, “Are You Sure.” It’s this staunch waltz, so blunt and to the point. I just loved it. Shortly afterwards, I’m on tour with him, and one night we’re on the bus. Something was passed around, and I got painfully high. Like, I didn’t know how I was going to exit the situation. But somehow, I got up the courage to say, “Do you ever sing that song anymore, ‘Are You Sure.’ ” The look on his face was so surprised. But he reached back, and out of a magic puff of smoke pulls out Trigger, strums, and sings, “Are you sure this is where you want to be?” Then he asked if I’d want to record it with him. Uh, yeah. 

Late one night, when I made my second album, Pageant Material, we turned off all the studio lights, got into this trippy mindset—I made all the guys in the band wear sparkly tiaras—and put down a version of it. Then I got that to Willie, who sang on it, and his guitar solo kills me, still. It’s so out there. I love that he’s still willing to take musical risks like that.

These interviews have been edited for clarity and length.

This article originally appeared in the February 2023 issue of Texas Monthly with the headline “The Sound in Our Minds.” Subscribe today.