What Laura Ingraham attempts to do in "The Obama Diaries" falls apart in my opinion. It turns out to be a somewhat surreal rant. By way of comparison, I later thought of the 70's parody: "Energy Crisis '74" by Dickie Goodman (which reached #33 on the Billboard chart at the time). That song was a mock interview of the President (although President Nixon was never mentioned by name) and other world leaders. Each interview question was followed by a single line or two from a popular current song. It was hilarious! However, it would have been much less hilarious if it had been 3 hours long rather than 3 minutes long.
When we put words in someone else's mouth, to be funny, (and sometimes it can be funny!) we should be brief and the statement should have some basis in reality. Otherwise it resembles something more like a schoolyard taunting--that is, lacking in humor, and hinting of a smug echo of "nyah, nyah...nyah, nyah, nyah" --behind the back of a person you hold up as the object of scorn and derision.