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Willie Nelson’s Outlaw Music Festival Tour stopped at Cincinnati, Ohio’s Riverbend Music Center on Friday night, and fans were treated to an extended sing-along between the country legend and Sturgill Simpson, who joined him onstage for a playful rendition of “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.”

There’s a ramshackle charm to this particular version of the 1978 classic, which Nelson originally sang with Waylon Jennings. In a fan-captured video, Simpson — the primary support on select dates of this summer’s tour — and the band follow the lead of Nelson and his guitar, Trigger, as he plucks his way through the melody. The pair trades lines through the verses, with the crowd joining in heartily on the choruses.

Simpson stuck around through the end of Nelson’s headlining set that night for the grand finale, a rousing medley that can also be seen in a 12-minute fan video. It kicks off with a cover of the Carter Family’s “Will the Circle Be Unbroken,” which gets the Red Headed Stranger — a particularly spry-looking 85-year-old in this case — into full-on band leader mode, while Simpson trades licks on guitar with harp player Mickey Raphael. The jam finishes off with “Living in the Promiseland” and “I Saw the Light.”

Despite having to cancel some gigs over the winter due to a bout of the flu, Nelson returned this spring with a new LP, Last Man Standing, which went to Number Two on the country charts. His Outlaw Tour continues through July and, after a break, goes into September, with its next stop June 29th at Verizon Arena in Little Rock, Arkansas, where Simpson will again be on the bill.