Billy Strings Recalls Surreal Bob Dylan Encounter On Theo Von’s ‘This Past Weekend’

Billy Strings returned to Theo Von’s This Past Weekend podcast for a nearly three-hour conversation that touched on fatherhood, addiction, grief, his upcoming album and a recent injury. But perhaps the most captivating portion came when Strings recounted the unlikely chain of events that resulted in him sharing a stage with Bob Dylan.

Strings appeared on This Past Weekend for the second time, following his 2024 conversation with Von. The lengthy chat, featured on Episode #676 of the podcast, was recorded in Grand Rapids, Michigan.

The Dylan story began long before Strings actually met the legendary songwriter. As Strings previously explained in a 2025 interview with Relix, he had intended to write Dylan a letter while staying at Austin’s Saint Cecilia Hotel. He took some hotel stationery with him but procrastinated for an entire year. When he eventually returned to the same room and found the paper still in his bag, he finally sat down and wrote the letter.

Strings never expected to hear back.

Then came an encounter at the Hollywood Bowl during the Outlaw Music Festival Tour concert on May 16, 2025. Dylan was walking through after his performance when he spotted Strings and addressed him by name.

“Man, thanks for the letter,” Dylan told him, according to Strings’ account.

The moment became even more surreal when Dylan told Strings, “I listen to you all the time.” Strings said that when the two shook hands, his hand tingled for the rest of the night.

The story took another extraordinary turn a week later. Strings was in the green room after his own set when a woman walked in and told him that Dylan wanted him to play that night.

Strings joined Dylan onstage for “All Along The Watchtower,” a song Dylan originally recorded in 1967 and that became even more famous through versions by The Jimi Hendrix Experience. The performance took place in Spokane, Washington on May 22, 2025.

On Von’s podcast, Strings revisited the experience as something that transcended simply getting to play alongside one of his musical heroes. “The cool thing about that too is that was my favorite song they were doing,” the guitarist explained. “And that’s the one he asked me to play on.”

Strings said the collaboration passed by in a heartbeat. “He sang the second verse and then he looked at me. I played and passed it back to him, we had a little musical conversation and that was it. I played with Bob Dylan.”

Strings described Dylan’s presence as overwhelming and the encounter as a profound moment of connection and validation. Afterward, Dylan came into Strings’ green room to thank him. “He sucked the oxygen out of the room,” he remembered. The guitarist introduced Dylan to his band, but Bob wasn’t having it and “dipped.” Strings also received a note from Dylan later, adding another personal touch to an experience he already considered extraordinary.

“It just said: ‘thanks for playing, I think you’re great.’ He said, ‘like my friend Jerry Lee [Lewis] told me a long time ago, I think you’re going to be around for a long long time.’ I was in the back of my bus reading this and I just cried.”

The Dylan story was just one portion of Strings’ wide-ranging return to This Past Weekend. The guitarist also spoke candidly about the loss of his mother, his history with addiction and his decision to pursue a different path after becoming a father. His forthcoming album, So Much For Goodbyes, is due out August 28 and serves in part as a tribute to his mother, featuring artwork she created. Out today is “10,000 Miles From A Friend,” the latest preview of the LP.

Strings also discussed breaking his leg in a skateboarding accident, the challenges of managing pain medication following surgery and how fatherhood has changed his relationship with music and life on the road. The episode concluded with Strings performing solo acoustic versions of “Groundhog” and “I’m One of Those.”

Watch Billy Strings’ latest appearance on This Past Weekend With Theo Von below.