I've been playing around with Stardock's The Political Machine 2008, which arrived in the mail a couple of days back.
While dealing with a serious topic, its graphics give the game a light-hearted feel. After working through the tutorial, I made the mistake of jumping into Campaign mode, which pitted my candidate of choice - Al Gore - against... Ulysses S. Grant.
'twas then I realized that the campaign mode runs you through a series of elections against historical figures. Beating Grant unlocked Richard Nixon, and so forth. What I really wanted to use was the Quickplay mode, which allows you to pick your opponents. So I ran Gore against McCain. And then Obama against McCain with Gore as VP. And then an Obama-Hillary slate. McCain, for some reason, kept picking Dick Cheney as his running mate.
While not a truly hardcore sim, the game does get you focused on electoral votes, campaign finances and the whole red state-blue state thing. Based on my early impressions, it's well worth the $20 asking price. I'll have more to say in my Philadelphia Inquirer column on June 27th.