Answers revealed in the comments.
GAME 1
Only five U.S. cities have had a World Series champion, an NBA champion, a Super Bowl champion, and a Stanley Cup champion.
GAME 2
Author Kurt Vonnegut wrote three novels that were nominated for the Hugo Award for Best Novel, all of which were published before 1970. Name two of those three novels.
Editor’s note: I don’t usually post photos with these final questions, but this reminded me of too funny of a scene from the 1986 film “Back To School” to NOT do a couple of memes! And here goes with a very funny piece of dialogue from the movie, where Rodney Dangerfield’s character hires author Kurt Vonnegut to write a paper on his works, since he didn’t do the assigned reading. The top meme shows his professor, who flunks him on the paper.
hebspeaks 
Game one answers:
Chicago
Boston
Philadelphia (I actually knew all three of these cities…on a sportsball final, which is a rarity!)
GAME 2 answers (only knew one of those)
The Sirens of Titan
Slaughterhouse-Five
Cat’s Cradle