This Past Weekend w/ Theo Von
This Past Weekend w/ Theo Von

Billy Strings

August 20, 2026

AI Summary

5 min read

Billy Strings walked into the green room at the Hollywood Bowl, and Bob Dylan walked right up to him. Not to make small talk—Dylan doesn't do small talk. He said, "Let's do 'All Along the Watchtower.' Play after the second verse." Then he walked away. No hello, no goodbye. Just information. That was the entire interaction until later, when Dylan showed up in Strings' green room, sucked the oxygen out of the room, thanked him for playing, and then—mid-introduction to Strings' band—turned around and walked out again. A few nights later, a message came through Dylan's manager: "My friend Jerry Lee told me a long time ago—you're gonna be around for a long, long time."

The weight of inheritance

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What you'll learn

  • 1 (00:30) **Introduction & The Stomping Grounds** - Theo introduces Billy Strings as a three-time Grammy winner and they talk about growing up near Grand Rapids, Michigan.
  • 2 (05:59) **Local Legends and the Hard Road** - Billy tells stories about childhood friends who became local legends, and the tragic toll of addiction in his hometown.
  • 3 (19:19) **The Death of Kevin Clayton & Early Loss** - Billy details the final days of his friend Kevin, who knew his addiction was out of control before he OD'd.
  • 4 (34:51) **The Broken Leg & The Wolf Man Cane** - Billy shows off his cane, a replica of the one from the 1941 film *The Wolf Man*, and recounts the story of breaking his leg.
  • 5 (46:34) **The Hospital, Fentanyl, and the K-Hole** - Billy walks through the chaotic aftermath of the break, from the police escort to the intense hospital drugs.
  • 6 (55:51) **Post-Surgery, Pain Management, and the Addict's Brain** - Billy talks about the recovery, giving his wife control of his pain meds because he knows he is an addict.
  • 7 (65:51) **Defining Addiction & Finding Mom's Stash** - Billy and Theo explore what addiction feels like: a shadow with its own game plan.

+ Full timestamped outline available in the app

Show Notes

Billy Strings is a Grammy award-winning musician and songwriter from Muir, Michigan. His latest album “So Much For Goodbyes” is out August 28th. 

Billy returns to talk to Theo about how being a dad has transformed him, breaking his leg in a freak skateboarding accident during a show, and how he’s honoring his mom’s unique spirit through music. 

Billy Strings: https://www.instagram.com/billystrings/ 

Recorded at Mackinaw Harvest Studios: https://www.mackinawharvest.com/ 

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Music: “Shine” by Bishop Gunn This Past Weekend w/ Theo Von