Wiley and the Checkmates from Oxford, Miss. are touring as an eight-piece with Wiley and a younger woman, Amber Knicole, handling the singing. They have scheduled two free shows at The Comet in Northside – this Thursday and again on May 15. For 66-year-old Herbert Wiley, this second time around may become much bigger than the first. In 1960, not long out of high school, he formed the first Checkmates, a six-piece band that became club favorites in Mississippi and Memphis and played throughout the South.