Introduction
During the pandemic, I was booked to perform at Luck Reunion—the week the world shut down. I was over the moon—it was bucket-list stuff. This wasn’t just any festival; it’s a small, exclusive event held every year at Willie Nelson’s ranch in Luck, Texas. You’re basically in his backyard, walking through the sets from Red Headed Stranger. You’re stepping through a piece of musical history—it felt like more than just a gig.
When everything went silent, I was devastated. But Matt Biser, who organizes the festival, reached out and said, “We’re moving it online. We want each artist to perform a couple of songs—would you like to do one?” So my guitarist and I “beamed in” from a record shop in Auckland, New Zealand. I ended up wedged between Lucinda Williams and Paul Simon—something that would never have happened in real life. It was surreal how incredible the virtual world was.
Unbeknownst to me at the time, Willie and Annie—his wife—and their family were all watching the whole livestream. As soon as my set began, Matt’s phone blew up with messages from Annie: “Who the hell is this? Oh my god, we love her.” She followed me on Twitter, and I just thought it was a lovely new fan—until my brother noticed and said, “Do you realize who’s talking to you? That’s Willie’s wife.” I immediately replayed everything I’d said to her in my head!
We chatted for a couple of months before she even followed my brother. Eventually, Annie gave me her phone number, saying, “Let’s text—no need to just use Twitter.” That friendship became a beautiful silver lining amid lockdown.
After some time, I went into the studio to record a new album. I’d written a duet with a friend, Delaney Davidson—both of us had recently lost fathers—and the song pulls everything from your heart. I sang the first verse and thought the second should be my dad. My brother half-jokingly said, “Why not ask your new best friend, Willie?” I laughed, but the idea grew on me. I was terrified of jeopardizing my friendship with Annie by asking, so I carefully prefaced it: if it was a no, that was totally fine—I didn’t want things to be awkward. She encouraged me to send it, saying Willie could decide. So I did. A few months later, Willie said he loved it, even comparing it to Patsy and Marty—high praise, given he’d written Patsy’s biggest hit.
We didn’t meet in person for about another year—New Zealand’s borders were still closed. Willie recorded his part remotely and sent it back. I remember being out on a walk when Annie texted me to say it had arrived. I raced home, and my husband and I listened on good speakers—and both of us just cried. Hearing our voices together, impossible to describe, so surreal.
Then finally, when our borders opened, I flew to Luck Reunion—just in time for them to hold it again. Annie texted me before the event: “He wants you to come over the house for a little run-through before tomorrow.” I tried to stay calm, but when we got there, I could actually hear him breathing—and I was terrified! We spent a couple of hours waiting, rehearsing, until we walked into Willie’s living room. There he was, relaxed in a T-shirt tucked in joggers, sitting at the kitchen counter like a laid-back grandfather. No intimidation, no celebrity aura—just a warm, humble man.
We all sat around with guitars and sang together—my verse, then the chorus—just two voices, no microphones, no production. Annie even joked beforehand: “Roseanne Cash says singing harmony with Willie Nelson was harder than giving birth.” No pressure, right? But it was utterly beautiful. Willie has this way of weaving around you—if you just stay in your own groove, he’ll float around you effortlessly. At one point, he stopped and said, “That’s a good line right there,” before continuing. And I thought: “No one else’s opinion matters—if Willie likes it, that’s it.”
That moment—how music bridged a virtual connection into genuine friendship, opening doors through a concert that almost never happened—is the most precious gift I could ever ask for.