VIDEO: Billy Strings Talks Playing Poker With Willie Nelson, Performs 'Escanaba' Live on the Stern Show

Grammy-winning bluegrass sensation Billy Strings made his Stern Show debut Wednesday morning, sitting down to chat with Howard about his latest album, “Highway Prayers,” and his love for the guitar, which is something he and the King of All Media very much have in common. In addition to performing live in the Stern Show studio and recording an exclusive concert for Howard 101, Billy regaled listeners with fascinating stories from his life, upbringing, and extraordinary career. The singer, songwriter, and instrumentalist opened up about everything from who he thinks are some of the greatest living musicians to how the Super Mario Bros. theme song encouraged him to level up his guitar playing.

He also spoke about collaborating with outlaw country legend Willie Nelson on their Grammy-nominated 2023 track “California Sober,” a rollicking jam which makes the case for weed over the “hard stuff.” But when talking about how the two of them unwound after their recording session, Billy said Nelson seemed less interested in getting high than in playing a high-stakes game of poker.

But Billy wasn’t complaining. In fact, he savored the opportunity to swap stories with the “It’s All Going to Pot” crooner and his pals. “I’d spend another thousand to sit in that chair and bullshit with those guys,” he said, adding, “Listening to them bullshit each other and tell jokes and talk shit to each other was like the highlight of my life. I mean, I was sitting there right where Johnny Cash and Kris Kristofferson did.”

The surreal encounter didn’t end there, either. Billy also got a chance to rock out on Willie’s legendary acoustic guitar, Trigger. “I asked him, ‘Can I pluck a note?’ He said, ‘Yeah, go ahead,'” Strings recalled with a smile before showing Howard the bluegrass song he played, “Black Mountain Rag.”

“You’re living the dream,” Howard marveled.

Billy could barely believe it himself. “The other night on stage at the CFG Arena in Baltimore, packed to the brim … I looked way up in the back corner,” he recalled. “I saw these people dancing, and I had this realization like, ‘Holy shit, whoa! This is real life and I’m actually standing here doing this.’”

“Doing it” may be an understatement. In addition to collaborating with stars like Dierks Bentley and Post Malone in the studio and performing alongside iconic acts ranging from Phish to Bob Dylan on stage, the 33-year-old phenom is currently headlining his own massive arena tour, bringing bluegrass to the masses in a way few artists have done before him.

Thankfully for Howard and his listeners, Billy and his band brought a little bluegrass to the Stern Show as well on Wednesday morning. Enjoy his live in-studio performance of “Escanaba” (below).