Billy Strings, 21st Century Bluegrass Rock Star, Is Trying Very Hard To Be Good

Anastasio misread Strings’ request for the guest list as an ask to sit in. “Let’s dooo it!” Anastasio responded immediately, and then: “Talking to the guys right now! Excited!” When, a month later, I told Anastasio about his mistake, he laughed a long time. “He didn’t think he was going to play with us?” says Anastasio, pulling up his text thread with “Billy Strings Real.” “I thought he meant come in for a guest spot.”

The morning of that first show, Anastasio dispatched a list of 16 potential songs for the next two nights, so Strings worked doggedly to learn them all until the moment he walked onstage. By the time he began playing, his left hand was already aching from all that solo rehearsal. He knew he was joining one of the tightest jam bands in history, with 40 years of experience; with that old self-doubt creeping in, he didn’t want to flub it.

“I didn’t want to piss Phish fans off, you know? I didn’t want to go out there and play a big wrong chord, which I probably did several,” he says, chuckling. “But at least I practiced.”

Two weeks later, just days before he would finally end his summer tour at the Forum, he had a few days off again in Los Angeles. He was due for meetings with record-label executives and other industry types, but Judd Apatow told him he should come down to Largo, the club that Brion helped make famous with his weekly residencies. Indeed, Hollywood has been calling lately. He says Matthew McConaughey asked him possibly to play a pirate in a movie, but he couldn’t swing it because of his touring schedule. He and Apatow are scheming on a potential documentary about Strings’ life, getting some early footage now.

The comedian Mike Birbiglia was hosting a benefit at Largo for YMCA Los Angeles, an institution that comes up repeatedly in his work. Apatow told Strings he should play something. He had never even seen standup comedy live until he arrived, and he was terrified when he finally sat down on stage, with only a few hundred people staring back at him. Was he supposed to be funny?

“My whole thing was, ‘What am I doing here?’” he says. “I just got on the mic and said, ‘Well, I’m not sure how I got roped into this shit.’ Everybody started laughing. Everybody loved it.”

It occurred to me that this question—“What am I doing here?”—has framed so much of Strings’ story, from the excitement to the anxiety, from the promise to the potential pitfalls. He was a kid in a tough family situation who used bluegrass to get noticed. And then, against most odds, that old form of American music, so often a punchline itself, made him an unlikely star, with all the complexity that entails.

He buys watches that can cost more than a car with the guidance of his buddy John Mayer but writhes on the floor in agony from a stomach problem he attributes to exhaustion and stress. He is pulled between the intimacy of tiny shows where he can see people’s expressions and massive ones with relatively faceless crowds that will give his son opportunities his father never had. On the eve of his first studio album for a major label—a label he signed to because he wanted to be in the same empire as Hendrix and Zeppelin—Strings’ question has become, much like he sings on Highway Prayers, “What am I going to do here?”

When Strings and I first met in 2021, I hoped he could keep it together, that his sudden post-pandemic rise didn’t rupture his personal version of sobriety (bud and occasional psychedelics, nothing else) or the electrifying sense that he was finding a new path through the music that raised us both. As we finished our loop around Grand Rapids and got back to his tour bus, I no longer worried about that. Instead, I wondered how much he wants this to keep growing, how much longer he can stand it all scaling up. So I asked.

He repeats the question, leans forward even more, and then returns to the ultimatum he delivered when he stormed off stage in Sweden, almost exactly a year ago. “I need to do more than tour my fucking ass off. We do that, and it seems like it’s paying off,” he says. “I need more time for myself, too. I can’t just work my life away, or this shit’s going to kill me.”

He climbs out to give me a hug, says he’s glad he didn’t cancel, and then heads back home, ready to wait to become a dad.