In an excellent new profile on Billy Strings published by men’s fashion and culture magazine GQ, the bluegrass star speaks candidly about his struggles to stay sane and fulfilled as his popularity continues to explode—a theme writer Grayson Haver Currin eventually boils down to the simple yet weighted question, “What am I doing here?” During the conversation, he speaks highly of various people whose approaches inspired him or helped him along the way, including Trey Anastasio and John Mayer.

While recounting a night on his 2023 European tour when the rigors of the road and sleep deprivation nearly pushed him to break his sobriety, Billy Strings explained how he looked to Trey Anastasio for guidance:

Instead, he picked up the phone: “I called Daddy,” Strings says with a mischievous grin. He is talking about Phish guitarist Trey Anastasio, whose band broke up in 2004 amid a cloud of bad playing and drug addiction. After his arrest for heroin possession in 2006, Anastasio got sober and ultimately reunited his band for a brilliant and ongoing new phase; he also became an ardent advocate for recovery and mutual support.

When Anastasio was in his late 20s, not much younger than Strings himself when he asked for help, Phish opened for Carlos Santana. The guitarist became Anastasio’s instant mentor, offering advice about how to stay sane on the road as crowds and expectations ballooned. He told him to go home often, to not spend too many consecutive weeks on the road. Strings sounded defeated, so Anastasio passed along some of that received wisdom.

“You can get pretty deep in Europe, with the time changes and the buses,” Anastasio tells me. “It didn’t surprise me when he called, because I was watching from afar: ‘Well, I was waiting for this!’ My phone is always on for Billy, because I want him to play until he’s 100. He could, and most people can’t.” 

Billy speaks about Trey once again when discussing the miscommunication that led to his recent two-night sit-in with Phish in Grand Rapids, MI:

In early August, Strings found himself with a rare week off. … He was going to be in Western Michigan rather than at home in Nashville, so he could be closer to Ally’s family as they awaited their son’s birth. There were bassinets to build, cradles to construct. He remembered that Phish were coming to Van Andel Arena, a relatively small room in Grand Rapids, for two nights for the first time since 1998. He sent Anastasio a text: “You think you could float me a couple guest spots?” 

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.” 

While speaking about his urge to downsize his elaborate, arena-oriented live shows and go back to staging more intimate performances, Billy Strings invokes John Mayer and his recent solo acoustic tours, during which he would play to arena crowds by himself. That leads to a discussion about Strings’ friendship with Mayer and how they’ve bonded over their love of watches:

Strings is back in [Grand Rapids, MI’s] the Pyramid Scheme today for an early afternoon photo shoot. When one of the owners, Tami VandenBerg, asks for a selfie, he puts his arm around her, grins, and poses. When it’s done, he asks for his own favor. “Do you guys ever set up chairs and do a quieter thing? We should do that sometime,” he asks, motioning to me. “I was just saying to him I struggle playing arenas and stuff with a bluegrass band without a drummer. I’m trying to rock these people out with a banjo and a guitar. I could sit on a stool and just play.” 

This interest in downsizing, which Strings mentions a lot, stems in part from a new pal, John Mayer. In 2023, Mayer went on a solo tour of very big rooms. Tickets were in such high demand he added a second leg. Mayer’s profit margins stunned Strings, though he suspects he’s not in that league yet. “God damn,” he says, chuckling, “he was packing arenas, playing by himself. I thought, ‘Dude, I should do a solo tour. I could buy another watch.’”

… He’s assembling watches himself at home now and designing a piece with Joshua Shapiro, the Los Angeles watchmaker who recently debuted the first watch made in the United States since 1969. Its features will mirror a vintage Martin D-28 and the sound holes of a fiddle. He pulls a dial he made a week or so ago using Shapiro’s antique machines from his wallet, secreted there like some treasured ticket stub or guitar pick. “It’s like guitars. I like collecting them,” he says with the enthusiasm of a kid explaining his favorite toys. “It’s a tool, and it’s beauty.” 

Other topics discussed include his desire to play small, intimate rooms, his struggles with self-confidence and past trauma, his recent appearance at a star-studded L.A. comedy show, the documentary Judd Apatow is starting to make about him, his recent gig with Michigan metal band Flesh and Blood Robot, how Bill Kreutzmann‘s invitation to write a song with unearth Robert Hunter lyrics saved him from a self-doubt spiral, his impending fatherhood, the recording process for his new album, Highway Prayers, and much more.

Read the full GQ profile on Billy Strings here: Billy Strings, 21st Century Bluegrass Rock Star, Is Trying Very Hard To Be Good.

Of note, the Billy Strings feature is by the same writer who recently embedded himself with Phish at Mondegreen for a previous GQ piece. You can read that feature here.