People like Keith Olbermann and Jon Stewart and Rachel Maddow might be entertaining (Stewart way more than Olbermann and Maddow, in my view), and they might even be smart (same), but they only talk about what their bosses allow them to talk about. If you're going to them to find out what political outrages to get upset about, you're using them wrong.
If Jon Stewart and Keith Olbermann and Rachel Maddow and all the rest of them are talking about an issue, it's one that Those in Charge don't care about.
What you should be upset about, and trying to push into the wider discourse, are the things they aren't talking about. Because those are the things that Those in Charge don't want you to think about.
(The same would go for people like Rush Limbaugh and Glenn Beck, but unfortunately the things they crap out every day are actively, immediately harmful, rather than passively, long-term harmful like the line their "left" counterparts spew, and must be actively, immediately countered. Which is of course also part of The Plan.)