Answers revealed in the comments.
GAME 1
In the 1990s, songs performed by Bette Midler won back-to-back Grammy Awards for Song of the Year. Name both songs.
GAME 2
Fifteen schools have had at least a 40-year drought between appearances in the NCAA Division I Men’s Basketball Tournament. The three most-recent of those droughts to end did so in 2004, 2012, and 2016. Name one of those three schools.
hebspeaks 
Game one answers
“Wind Beneath My Wings”
“From a Distance”
GAME 2
answers:
Air Force
Yale
Harvard