Answers revealed in the comments.
GAME 1
What TV series, which originally aired on CBS beginning in 1984, introduced a brand-new character to a long-running franchise named Skeeter, who was the twin sister of one of the other characters? The series was rebooted in 2018 on Disney Junior.
GAME 2
In 1965, an advertisement appeared in Daily Variety and The Hollywood Reporter that was looking for “4 insane boys, ages 17-21” who “have courage to work”. What group, which still exists today, did those boys end up creating?
game one answer: Muppet Babies
Game two answer: Monkees