Answers revealed in the comments.
GAME 1
What singer-songwriter and guitarist won the Grammy Awards for Best Male Pop Vocal Performance in 2003, Song of the Year in 2005, and Best Pop Vocal Album in 2007?
GAME 2
The Alliance of American Football, which had its inaugural games on Saturday, consists of eight teams, three of which are located in metro areas that also served as the home for XFL teams in its only completed season. Name one of those three metro areas.
Game one answer:
John Mayer
GAME 2 answers:
Birmingham, AL
Orlando, FL
Memphis, TN