As we move away from entertainment, my knowledge-base gets waaaaaaay less specific, so you should have a much better chance of getting these.
History and Politics:
1) BLANK for America was consistently the lowest-polling candidate for the 2016 Republican Party presidential nomination. Who is BLANK?
2) Abbott and Costello are the surnames of which two prominent Australian politicians?
3) Which former mayor of Toowoomba led the campaign against treated sewage water during the drought?
4) What was Toronto's name before it was Toronto?
5) Why did Mark Hofmann start bombing Mormon document collectors?
6) In which year was Australia Federated?
7) It's crazy that the guy who comes in second gets to be Vice President. We can change that. You know why?
8) Why didn't the Ancient Egyptians ride horses?
9) Which was the first state to ratify the US Constitution?
10) Who was the youngest female convict on the First Fleet?