After helping Willie Nelson celebrate his 90th birthday at Hollywood Bowl earlier this year, Bob Weir joined the Red Headed Stranger on stage at his Outlaw Music Festival stop at CCNB Amphitheatre at Heritage Park in Simpsonville, SC for a medley of classic country tunes “Will The Circle Be Unbroken?” and ”I’ll Fly Away”.

Weir first played a set with Wolf Bros and The Wolfpack that featured a sit-in by Willie Nelson’s harmonica player, Mickey Raphael, who joined the band sporadically throughout the set for songs including “Me And My Uncle”, “Truckin'”, “Shakedown Street”, and “U.S. Blues”. Weir then returned the favor during Willie Nelson & Family’s set, playing guitar and singing background vocals during the “Will The Circle Be Unbroken?”/”I’ll Fly Away” medley. He then stuck around to end the show with “It’s Hard To Be Humble”, a song originally written and recorded by Mac Davis in 1980 and later covered by Willie on his 2019 album Ride Me Back Home.

Check out fan-shot videos of the collaboration below.

Bob Weir & Wolf Bros will headline Ting Pavilion in Charlottesville, VA tonight, Wednesday, September 13th before linking back up with the Outlaw Music Festival at Saratoga Performing arts Center (SPAC) in Saratoga Springs, NY on Friday the 15th. For more on the festival, click here, and to purchase tickets visit the festival website, Willie’s website, or Bob Weir’s website.

Willie Nelson & Family With Bob Weir – “Will The Circle Be Unbroken?” > ”I’ll Fly Away” – 9/12/23

[Video: RS T’ner]

Willie Nelson & Family With Bob Weir – “It’s Hard To Be Humble” (Mac Davis) – 9/12/23

[Video: RS T’ner]