Answers revealed in the comments.
GAME 1
Since 2000, four different bands or artists have been nominated for the Grammy Awards for Best New Artist, Record of the Year, Album of the Year, and Song of the Year at a single ceremony. Name any one of those nominees.
GAME 2
Not including any overseas territories, which country that is a member of NATO extends the farthest south?
hebspeaks 
Game One Answers
India.Arie (2002)
Amy Winehouse (2008)
fun. (2013)
Sam Smith (2015)
GAME 2 answer:
United States