The one place I felt he was being somewhat hypocritical was about the whole "tea-bagger" thing. Long before Rachel and Ana Marie had their giggle-fests and even before David Schuster was snarking about the "Dick Army," I remember Jon playing the clip of the guy saying "Teabag the fools in Washington," and going off a riff on it that was as snarky and filthy by implication as anything that got said on MSNBC in the halcyon weeks before the folks who were HAPPILY calling themselves "tea-baggers" bought a clue.
I also thought (and this could just be me) that he was playing up to Rachel as the voice of sanity at MSNBC, as opposed to Keith and the others. Like the time she was on his show and he called her "Marilyn" whereas the rest of the network were the Munsters.
If you get a chance to download the whole interview from MSNBC or elsewhere, I'd strongly recommend it.