India, Sept. 23 -- Tyler Childers has played to sold-out arenas on several occasions, but on Wednesday, September 17, he put on a full-scale arena show for just 20 people, and then handed out $1000.

The event started as part of a fundraiser for Shriners Children's Lexington, promoted through Childers' fan club, the Hickman Holler Hunting Club. Ten fans who donated were randomly picked and told they could bring one guest to a secret show. But none among them knew the location.

Fans were shuttled to an undisclosed spot in Lexington, Kentucky, only to find themselves walking into Rupp Arena. That is where Childers and his band, The Food Stamps, had set up for a final rehearsal ahead of his upcoming Snipe Hunter tour. Instead of empty seats...