Answers revealed in the comments.
GAME 1
What singer attended Erasmus Hall High School with Barbra Streisand, where they performed together in choir about 20 years before they reached #1 together on the Billboard Hot 100?
GAME 2
According to a report released by the International Institute for Strategic Studies, 17 of the 20 countries in the world with the most ACTIVE military members are either the U.S. or at least partially located in Asia, geographically. Name 1 of the other 3.
Game one answer: Neil Diamond
Game two answer: Brazil, Colombia, Mexico