Answers revealed in the comments.
GAME 1
When listed alphabetically by last name, who is the first woman on the list of people who have appeared on the American cover of Rolling Stone magazine?
GAME 2
Catering only to the wealthiest travelers, what was the nickname for the Seaboard Air Line Railroad winter-only train that ran from New York City to Miami?
hebspeaks 
game one answer: Paula Abdul
game two answer: Orange Blossom Special