Answers revealed in the comments.
GAME 1
The singer who was born Leslie Sebastian Charles in Trinidad and Tobago in 1950 and had a string of top 10 hits in the mid-to-late 1980s, including three #1 singles, is better-known by what stage name?
GAME 2
With a little more than 50,000 people as of the 2010 census, what Eastern U.S. city is the 38th most populous state capital, but is still the most populous city in its state?
hebspeaks 
Game one answer: Billy Ocean
Game two answer: Charleston, WV