You could make a pretty humorous game by adopting an insult swordfighting system and having the chosen philosophers trade barbs built from their own quotes or ideas. The writing would be tough, and would likely require a lot of research, and in the end 80% of the jokes would sail over the heads of the non-philosophy majors of the world. Still, the concept itself is kind of funny to me.
But this idea reminds me of the post where Jay Barnson played Democracy, and described his run-through of the game as President of the United States. Okay, now we’re talking about competing political philosophies, which is a small subset of philosophy in general, but you can argue that this still meets the goals of the challenge.
The approach taken in Democracy is that you must run for president and then “do a good job” in order to get re-elected. This implies that somewhere in the many decisions you make in the game, there are right ones and wrong ones, which means that to a certain extent the game is taking sides, philosophically. (It also means that small / limited government types will have to adopt some other worldview for the purposes of the game, since a game where you run a limited government would be by design painfully dull.)
For example: Does banning guns reduce crime? Lots of people have opinions on this. They have statistics and charts to support their position, and a list of reasons why you should ignore the other guy’s statistics and charts. I have an opinion on this is well, which I will keep to myself in the hopes that the comments will follow my example. We can postulate all day on the right and wrong of the thing, what the result of a particular law will be, and what consequences one might face, but once we move the thing into the context of a computer game we move the debate into a simulated world where the answer was decided by the designer. In the game, you pass the law and you see the unambiguous results. This seems a little unfair, and is likely to chafe anyone that doesn’t agree with what the game world says will happen. Crime will go up or down, and you will be “right” or “wrong”. (I really hope that these are randomized from game to game, or else the whole thing will feel like little more than propaganda to those with differing opinions.) In this case the ideas are not so much competing against one another in the minds of the players and in the mechanics of the game as they are supported by portions of the simulated population.
Still, the real goal of the game is to hold office, not solve problems, so the player need not get hung up on philosophy as long as they are willing to abandon their own values in the pursuit of raw power. I’ve certainly done worse for much less in a lot of other games.