I just finished watching the first season of "Boss," a Starz series masterfully directed by Gus Van Sant. I judge it to be the most accurate depiction of politics I've ever seen on screen. It goes beyond the teachings of Machiavelli, becoming ideal groundwork for a series of lectures on public choice.
Advice to watchers: the series starts slowly, but picks up steam during the second half of the first season. It's extremely dark yet plausible. Kelsey Grammer grows in his role as the mayor of Chicago, episode after episode. What I find fascinating is the fact that party colors don't really matter for the story telling: the series works equally well would the mayor be a Democrat and his challengers Republicans or vice versa.
Warning: this series will forever kill any hope you may nourish about supposedly redemptive qualities of democracy and politics. No question that the world would be a better place if we could rely less on political representation and more on direct interpersonal relations and impersonal markets for collective action.
Enjoy the trailer: