Anastasio misinterpreted String’s request for the guest list as a request to be seated. “Let’s do it!” Anastasio replied immediately and then: “I’m talking to the guys right now!” Excited!” When I told Anastasio about his mistake a month later, he laughed for a long time. “He didn’t think he would do it play with us?” says Anastasio and calls up his text thread with “Billy Strings Real”. “I thought he wanted to come In for a guest appearance.”

On the morning of that first show, Anastasio sent a list of 16 possible songs for the next two nights, so Strings worked persistently to learn them all until he took the stage. When he started playing, his left hand was already hurting from so many solo rehearsals. 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 screw it up.

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

Two weeks later, just days before he would finally end his summer tour at the Forum, he had another few days off in Los Angeles. He was scheduled to meet with record company executives and other industry figures, but Judd Apatow told him to come to Largo, the club Brion made famous with his weekly performances. In fact, Hollywood has been calling lately. He says Matthew McConaughey asked him to possibly play a pirate in a movie, but he couldn’t make it due to his touring schedule. He and Apatow are planning a possible documentary about Strings’ life and are now getting the first footage.

Comedian Mike Birbiglia hosted a fundraiser at Largo for the Los Angeles YMCA, an institution that appears frequently in his work. Apatow told Strings to play something. He had never seen stand-up comedy live before he arrived and was terrified when he finally sat down on stage and only a few hundred people were staring at him. Was it supposed to be funny?

“My whole thing was, ‘What am I doing here?'” he says. “I just sat down at the microphone and said, ‘Well, I’m not sure how I got involved The Shit.’ Everyone started laughing. Everyone loved it.”

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

Under the guidance of his pal John Mayer, he buys watches that can cost more than a car, but writhes in agony on the floor with stomach problems that he attributes to exhaustion and stress. He is torn between the intimacy of tiny shows where he can see people’s expressions and huge shows with relatively faceless crowds that offer his son opportunities his father never had. On the eve of his first studio album for a major label – a label he signed with because he wanted to be in the same empire as Hendrix and Zeppelin – Strings’ question has become how he continues to sing Highway Prayers“What am I go to do here?”

When Strings and I first met in 2021, I hoped that he could hold it together, that his sudden post-pandemic rise was neither his personal version of sobriety (buds and occasional psychedelics, nothing else) nor the electrifying feeling he discovered destroyed a new path through the music that raised us both. By the time we finished our loop around Grand Rapids and returned to his tour bus, I wasn’t worried about it anymore. Instead, I wondered how much he wants this to continue to grow, how much longer he can bear to keep expanding it. So I asked.

He repeats the question, leans in further and then returns to the ultimatum he gave when he stormed off the stage in Sweden almost exactly a year ago. “I gotta do more than work my damn ass off. We’re doing this and it seems like it’s paying off,” he says. “I also need more time for myself. I can’t just work my life away or this shit will kill me.”

He gets out to hug me, says he’s glad he didn’t cancel, and then heads home, ready to wait to become a father.