It’s the type of routine where Jon Stewart is not the straight man. Usually Stewart feeds straight lines to the “correspondents” and reacts to their replies, and that’s fine; he represents us, the normal person trying to hold onto real-world logic while under bombardment from news-media inanity. But every once in a while, as in last night’s piracy routine with John Oliver, the writers will reverse it: they’ll make the correspondent the straight man, trying to do a serious report on an important issue, and Stewart will be the guy who’s focused on trivialities.
Not only is that kind of routine welcome as a change of pace, but it also parodies a very typical TV news dynamic, where the little-known but serious reporter will do a back-and-forth with the famous airhead anchor. In last night’s routine, Jon represented the vacuous celebrity anchor who only cares about soundbites, and John played the serious journalist, humiliated at having to fit his report into this stupid format. It’s funny because it’s real; every TV news anchor has incorporated some stupid pirate jokes into their coverage of this story.
It seems like when they do this kind of routine, it usually involves John Oliver. He’s so good at playing the self-hating reporter that it almost seems like a waste when he plays the more typical role of the arrogant reporter giving stupid answers to Jon’s questions. Which means that, unusually, he’s actually funnier when he’s cast as the straight man (because as the straight man, he gets to do the slow-burn anger at taking orders from Jon).