Answers revealed in the comments.
GAME 1
Who is the only woman to have at least six nominations for the Grammy Award for Best Comedy Album?
She was nominated in six consecutive years, beginning in 2009, winning in 2014 for her album Calm Down Gurrl?
She was nominated in six consecutive years, beginning in 2009, winning in 2014 for her album Calm Down Gurrl?
GAME 2
U.S. Route 66 officially existed from 1926 to 1985 and ran almost 2,500 miles through eight states.
Of those eight states, name two of the three that are the smallest by total area.
Of those eight states, name two of the three that are the smallest by total area.
hebspeaks 
Game One answer:
Kathy Griffin
GAME 2 answers:
Illinois
Missouri
Oklahoma
OMG…A ROUTE 66 QUESTION! Where were you when we had that awful, awful “Law and Order: SVU” question on Monday night? Sigh…