Seriously,
To have the brains necessary to understand the underlying material and translate it into common daily situations, to an audience that is only a little ahead of the curve (at the worst):
George Carlin!
Who else could deliver this as an invisible depth charge (set to go off on the way home, or the next morning), and disguised as a fun evening out? On HBO, no less.
Let's be honest, it wouldn't work at a WWE event. And Oprah, or more precisely, her audience, is not much better than the WWE crowd, only more refined in their appearance ( and probably less honest about what they are really like, and proceed to make airs about it, than the WWE crowd).
:D