Every episode of Darknet Diaries[0]. Episode 49 and the two Xbox Underground episodes are excellent, but regardless of where you start you cannot go wrong with Darknet Diaries.
He doesn't seem at all to be someone in the security research field.
Either he has those reaction because this is a mainstream podcast and purposely tries to have a "dumb" reaction for his audience (like in a children's film) or he doesn't seem to understand hacker culture at all.
BTW, you might want to check out /r/darknetdiaries/ on Reddit for discussion of the episodes. Jack drops by now and then to participate.