The Ken Rogers calls are great in kinda the same way as the thimble sketch from Mr. Show
You're talking about the Story of Everest, I presume...I was thinking of that in relation to Ken Rogers too, except the difference there is there's sort of an arc where it's hilarious the first couple of times, then gets purposely irritating the more it goes on, and then is kind of funny again at the end -- for me at least -- but with the Ken Rogers stuff I didn't really think it was that funny to begin with, and less so as it goes on.
Actually a great example of that "audience-punishing" humor done brilliantly on TBSOWFMU is none other than Coffin Talk. It worked in exactly that way for me, gut-busting for a while, then kind of annoying--but in a good way. Ken Rogers, on the other hand, is fast-forward material for a podcast listener such as myself. But I see I'm in a minority of one here, so you people enjoy your punishment.