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This game popped into my head for the first time in 15 years: PeaceMaker, a gov sim where you try to get a two-state solution
(en.wikipedia.org)
I remember reading about this game heralding a new era where you could "play the news" (a hilarious phrase that has been rattling around in my head for over a decade now). I think I booted it up once and clicked around for fifteen minutes way back when. Anyway it's associated with a deeply embarrassing memory from college when I saw my friend Hichem standing in the main hall at a Palestinian students' group poster board, and encouraged him to play this game "because it really lets you understand both sides" 
they made us play this as a class in my synagogue's sunday school.
my parents also had a copy on their 2009 macbook since they work for the synagogue part-time and I remember almost exclusively choosing palestine when I booted it up, though i don't exactly remember why as I was pretty indoctrinated at the time