Answers revealed in the comments.
GAME 1
Which 20th-century U.S. president signed the law that officially made Thanksgiving the fourth Thursday of November?
GAME 2
The four members of the country supergroup The Highwaymen combined to have only two top 10 singles on the Billboard Hot 100 as lead solo artists. Name one of those two songs, which peaked in 1969 and 1982, respectively.
Game one answer:
Franklin D. Roosevelt
GAME 2 answer:
“A Boy Named Sue”
“Always On My Mind”