Answers revealed in the comments.
GAME 1
John Mellencamp’s 1982 album American Fool produced his first two top five singles on the Billboard Hot 100. One was “Jack & Diane” – what was the other song?
GAME 2
What company topped the first ever Fortune 500 list in 1955? The company ranked #10 on the list in 2018.
Game one answer: Hurts so Good
Game two answer: General Motors