2. Rosanne Cash and Kris Kristofferson (Saturday)
A standing ovation from the crowd for 86-year-old Kristofferson, who joined Cash to sing “Lovin’ Her Was Easier (Than Anything I’ll Ever Do Again).” Kristofferson, who has attributed his well-documented memory troubles to Lyme disease, was a bit shaky yet movingly determined as he traded lines with Cash, whose father, Johnny, famously played with Kristofferson in the Highwaymen. Very poignant.
3. Sturgill Simpson (Saturday)
Best banter of the night came from Simpson, who told the audience, “There’s only one reason I’m not on a beach in South Asia right now, and that’s Willie Nelson.” He went on to confess something he said he’s never had the courage to tell Nelson, which is that the only reason he went to Nashville to make country records is “because I grew up listening to country records by Willie Nelson” — records, he added, that exist “outside of the box of what most people think country records can be.” Then he said that the only reason he signed to Atlantic Records is because Willie did, even though “that didn’t work out too well for me.” Simpson’s performance was just as strong: a tough but tender rendition of “I’d Have to Be Crazy,” the Steven Fromholz tune Nelson recorded in the mid-’70s.
4. Chris Stapleton (Saturday)
When you’ve got Stapleton on your show, you give him the chance to flex his soulful side, which is why he got two of the night’s most luscious slow jams: “Last Thing I Needed First Thing This Morning” and “Always on My Mind,” both of which he sang with gentle-giant warmth.
5. George Strait and Willie Nelson (Saturday)
It made sense that Strait and Nelson opened with their 2019 novelty tune “Sing One With Willie.” If there’s anything we know about Nelson, it’s that he loves to yuk it up. Strait is noticeably clean-cut compared to Nelson and many who graced this stage tonight, but that speaks to Willie’s range and the wide swatch of humanity that loves him. It was also a true delight to hear famously straight-laced Strait tell the audience that Willie “sang the s— out of” their next song, Townes Van Zandt’s “Pancho and Lefty,” when he cut it with Merle Haggard in the early ‘80s.