Sturgill Simpson stepped out of the shadows on Saturday for a surprise appearance at Farm Aid, where he performed Grateful Dead classics with Bob Weir. The reclusive singer-songwriter also appeared with Margo Price and others throughout the benefit concert held at Noblesville, IN’s Ruoff Music Center.

Simpson’s surprise appearance closes some loops and begins others, with Grammy-winner making good on his canceled 2021 set at Farm Aid. He was originally slated to perform at the concert’s triumphant return from behind the COVID curtain, but nixed the appearance along with a string of others due to ruptured vocal chords. The sparing concerts he did play between the 2021 return of live music and his injury proved to be his last until returning to the stage this past April for a brief appearance at Willie Nelson‘s 90th birthday celebration at the Hollywood Bowl. When Sturgill originally canceled his concerts back in 2021, he warned that it’d “be a long hot minute” before he returned to the stage. Well, it’s starting to appear that minute may be just about over.

Saturday’s surprise sit-in also deepens what appears to be Sturgill’s growing fascination and collaboration with Bobby Weir and the world of the Grateful Dead. It is perhaps no coincidence that less than two weeks ago, the members of Dead & Company (minus John Mayer) announced the launch of a new Mexican destination event Dead Ahead featuring none other than Sturgill Simpson, Margo Price (who also joined in on Saturday’s sit-in), and many others.

As far as Saturday’s sit-in went, Sturgill showed his chops in the bluesy “Truckin'” which opened Bob Weir & Wolf Bros’ three-song set. This was no warm-up appearance nor an audition by Sturgill, however, as Bobby gave the alt-country icon a baptism by fire, throwing him straight into the Dead’s sprawling improvisational behemoth “Dark Star”. Simpson held his own in one of the crown jewels of Grateful Dead ’60s psychedelia, offering nothing too flashy but proving himself a team player who plays well with others among the guitar trio rounded out by Bob Weir and Lukas Nelson, who performed throughout.

Finally, the 45-minute set came to a close with help from Farm Aid chair Margo Price who ramped up the energy on the Crickets sing-along “Not Fade Away”. Simpson later joined Price during her set for a mix of both artists’ originals as well as a cover of Tom Petty and the Heartbreakers’ “Mary Jane’s Last Dance”.

Besides being a well-placed cover by one of rock’s great singer-songwriters, there may have been deeper meaning to the Petty cover. There was another big surprise looming around the corner at Farm Aid, as between sets by Neil Young and the evening’s closer, Willie Nelson & FamilyBob Dylan sauntered onstage for a surprise appearance backed by none other than the late Tom Petty’s backing band the Heartbreakers. Saturday marked Dylan’s first appearance at Farm Aid since the inaugural event in 1985, and included the Nobel Prize-winning writer’s old favorites “Maggie’s Farm”, “Positively 4th Street”, and “Ballad Of A Thin Man”.

Check out videos of Sturgill Simpson with Bob Weir playing Grateful Dead favorites courtesy of Doug Heck along with Live For Live Music‘s full coverage of Farm Aid here.

Bob Weir & Wolf Bros, Sturgill Simpson, Lukas Nelson – “Truckin'” – 9/23/23

Bob Weir & Wolf Bros, Sturgill Simpson, Lukas Nelson – “Dark Star” – 9/23/23

Bob Weir & Wolf Bros, Sturgill Simpson, Margo Price, Lukas Nelson – “Not Fade Away” (The Crickets) – 9/23/23