To understand more about tyranny, play a game with a group of kids (about 25 is perfect) where you decide whether to have a tyrant, and who should be the tyrant.
Most of the kids (all but five) will be ordinary people – men and women, mostly farmers. About half own land and half are landless laborers. Choose five to be rich men – oligarchs. Each of these five is going to try to make himself the tyrant, and the farmers will have to choose which one to support, or whether they’d rather keep the oligarchy (or set up a democracy).
First, the farmers should take a few minutes in small groups to figure out what their issues are. What do they want from a government? What are their biggest problems? (hint, the usual biggies are wanting some land to farm if they don’t have any, and being in debt). Then the farmers should take turns complaining to the oligarchs about their problems and demanding the solutions they think of.
Now, the oligarchs should try to respond as a group to these demands. What can they do to help the farmers? Or will they just threaten to kill the farmers if they don’t shut up? (But remember, the farmers are also the army).
Then, each oligarch gets a chance to convince the farmers that they should support him for tyrant. What promises should each one make? Finally, the farmers vote on what to do. Support one of the oligarchs to be a tyrant? Continue the oligarchy? Revolt and form a democracy?
Oxford First Ancient History, by Roy Burrell and Peter Connolly (1997). Lively interviews and pictures make the ancient Mediterranean come to life. For teens.
Geometric Greece: 900-700 BC, by J. N. Coldstream (2nd edition 2003).
Archaic Greece: The Age of Experiment, by Anthony Snodgrass (1981). Now perhaps slightly out of date.