Sturgill Simpson Recalls Bob Weir Telling Him To ‘Play Like You’

Sturgill “Johnny Blue Skies” Simpson reflected on how Bob Weir helped transform him from a Grateful Dead skeptic into a collaborator in a new Playboy interview conducted by JamBase contributor Grayson Haver Currin. Asked about his relationship with the Grateful Dead’s music before joining Dead & Company for Weir’s next-to-last concert, Simpson answered, “Nonexistent until about four years ago.”

Simpson explained that he rejected the Grateful Dead “out of ignorance” in his twenties after leaving the Navy and moving back to Kentucky. Bluegrass was his sole focus, and he found the Dead’s vocals difficult to connect with. He also associated the band with a local scene he viewed as cliquish and inauthentic.

That changed after Simpson sustained a vocal injury and entered what he described as a years-long “impostor-syndrome spiral.” His agent then relayed an offer from Weir to come to Mexico and sit in at the inaugural Dead Ahead destination event. Simpson told Weir that he was not especially steeped in the songbook. Weir replied, “Everybody tries to play like Jerry, and I want you to play like you.”

Weir subsequently sent Simpson a list of approximately 70 songs to learn in three days. While “Scarlet Begonias” evoked Paris in the springtime for Simpson, he called “Me And My Uncle” the greatest honky-tonk country song of all time.

“Morning Dew” was the Grateful Dead song that hit Simpson hardest. He connected it to the isolation that can accompany a life in music and the loss of friends, heroes and childhood friends as paths diverge. “Morning Dew” was “a kick to the chest,” he told Currin.

Simpson then reflected on singing the song with Weir at Dead & Company’s Grateful Dead 60 concert in Golden Gate Park, one of Weir’s final appearances. “Getting to go out and play that song, specifically that song with Bob at the end of his life, I remember being hyperaware of the immense serendipity of it all,” Simpson said. “Looking out at that crowd in that place in that park in that minute with that man and that song … all led me to that moment. It was like, ‘All right, this is why I’m here. How do I take this energy to my band?’ It was fucking beautiful, man.”

Simpson was in Spain when he learned Weir had died. “I hate to say it, but I remember thinking, ‘Yeah, of course he did. What else could go wrong this year?’” he said. “Whether it’s your grandfather or Merle Haggard or John Prine, you meet these guys and become friends and start to feel comfortable and really talking and being open and learning, and one day, they’re just fucking gone.”

Asked what he learned from Weir, Simpson offered a concise answer: “That it’s impossible to make a mistake.”

Weir’s invitation led Simpson to participate in Dead Ahead in 2024 and 2025. He then joined Dead & Company for “Morning Dew” during the second of three Grateful Dead 60th anniversary concerts at San Francisco’s Golden Gate Park in August 2025. Earlier this month, Simpson honored Weir at Berkeley’s Greek Theatre and credited the late guitarist with inspiring his return to touring.

Sturgill Simpson will bring his Johnny Blue Skies & The Dark Clouds outfit to Denver’s Ball Arena tomorrow, September 23. The tour continues through October 30.