Sturgill Simpson Reveals He Was Ready To Quit Touring Forever Before Being Inspired By The Late, Great Bob Weir

Sturgill Simpson

Thank God for the late, great Bob Weir.

At this point in his career, Sturgill Simpson has reached God-like status in country music. Arguably being the forefather of the independent/alternative country renaissance, along with the likes of Tyler Childers, Cody Jinks and more, the Kentucky native has probably influenced your favorite artist in some capacity or another in the past decade.

The “Long White Line” singer, for lack of a better term, has nearly gone in every direction possible. Delivering an atmospheric journey on the Grammy-winning A Sailor’s Guide to Earth, a full-blown rock adventure in SOUND & FURY, a bluegrass double album on Cuttin’ Grass, the narrative-driven concept record, The Ballad of Dood & Jaunita, and finally being rebirthed as Johnny Blue Skies on Passage Du Desir and his latest album, the dance and protest-inspired Mutiny After MidnightOf course, this doesn’t even mention his first two albums, High Top Mountain and Metamodern Sounds in Country Music, which are all but standards in the genre at this point.

Beyond his incredible studio work, one of the biggest draws to Simpson (and now Johnny Blue Skies) as an artist is his unbelievable live shows, which typically span well over three hours straight of pure music per night, and his ability to share the stage with some of the best acts in music period. Of course, this includes collaborations with the likes of Chris Stapleton, The Black Keys, the late John Prine and most notably, the Grateful Dead offshoot, Dead & Company.

In particular, the “I Don’t Mind” singer has been a frequent flyer with Dead & Company the past few years, making multiple appearances with the band. Notably, he collaborated with Grateful Dead alumni in 2024 and 2025 at their Dead Ahead Festival, where they performed tracks like “U.S. Blues” and “Brown-Eyed Woman.” His last performance last year in San Francisco was particularly epic, where he delivered a 10+ minute rendition of “Morning Dew” alongside John Mayer and the late Bob Weir.

As it turns out, those shows with Dead & Co. and the late, great Weir, in particular, were incredibly crucial to his future, looking back nearly three years later.

During his show on his current Mutiny for the Masses Tour last night in Berkley, California, Simpson took time to reflect on his time with Dead & Company. Here, he’d admit that his time performing with the legendary jam band was a key turning point in his career, going as far as to reveal that he was planning on quitting touring. It was Weir, however, that accidentally brought the desire to continue playing shows back to the Kentucky native.

“Bob pulled me out of it. He didn’t know this; I never really got to tell him fully. I didn’t know if I would ever tour again. In ’23-24, I went to Mexico and sat in with ’em for about two hours, three nights and came home and called my agent. I said, ‘I want to go on tour.’

That was three years ago, and this has been the best three years of my life and my career playing with these guys. And I owe a lot of that to Bob Weir.”

After explaining how his wife broke the news of Weir’s passing, Sturgill would then reveal that he was wearing one of the late legend’s signature bolo ties before shouting out his wife and daughter, who were in attendance.

“I’m gonna wear this b*tch the rest of the tour, and we just want to say we love you.”

Watch here:

@kikiandsprinkles We had no idea we would laugh, dance AND cry tonight. ❤️⚡️💙 Johnny Blue Skies sharing what Bob Weir meant to him and how Bob helped bring him back to the road was one of those moments we won’t forget. What a special night. So grateful we got to be there for it. 🎶 #JohnnyBlueSkies #BobWeir #GratefulDead #Deadhead #sturgillsimpson @gratefuldead @Bobby Weir ♬ original sound – KikiandSprinkles

Mutiny For The Masses Tour Dates

Sep 18 – Seattle, WA – Climate Pledge Arena

Sep 19 – Vancouver, BC – Pacific Coliseum

Sep 21 – Eugene, OR – Matthew Knight Arena

Sep 23 – Denver, CO – Ball Arena

Sep 26 – Kansas City, MO – T-Mobile Center

Sep 27 – St. Paul, MN – Grand Casino Arena

Sep 29 -Chicago, IL – United Center

Oct 2 – Nashville, TN – Bridgestone Arena

Oct 3 – Indianapolis, IN – Gainbridge Fieldhouse

Oct 6 – St. Louis, MO – Enterprise Center

Oct 7 – Columbus, OH – Nationwide Arena

Oct 9 – Pittsburgh, PA – Petersen Events Center

Oct 10 – Detroit, MI – Little Caesars Arena

Oct 13 – Boston, MA – TD Garden

Oct 15 – Philadelphia, PA – Xfinity Mobile Arena

Oct 16 – Brooklyn, NY – Barclays Center

Oct 18 – Washington, DC – Capital One Arena

Oct 21 – Raleigh, NC – Lenovo Center

Oct 23 – Charleston, SC – Credit One Stadium

Oct 25 – Atlanta, GA – State Farm Arena

Oct 27 – New Orleans, LA – Lakefront Arena

Oct 30 – Lexington, KY – Rupp Arena

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