Let's fill this with trivia about classmates, events, and maybe things from the yearbook!
Examples:
What was the musical production our senior year?
What was the score of the City High/West High football game our senior year?
From whose classroom were you likely climbing out a window - in the middle of class!

The catch - it's multiple choice so we have to come up with 2 to 4 answers per... Or don't! We can just list the questions here and read them off at the event and let people call out the answers... just thoughts. 
1) Where did City High play their varsity football games before Bates Field?
West High
U-High
Kinnick Stadium
The field at Longfellow Elementary
2) Where was the original City High?
West High
Hills
The Old Capitol
The old Central Junior High

3) This REAL part City High's past facilities would be a tough sell today.
A fish pond
Tower bungee drop
A shooting range
Valet parking