It's probably the political science junkie in me, but Tom Lehrer will always be my favorite comedic musician.
The Vatican Rag satirizes changes to the Catholic ceremonial procedures that came about in the 1960s. Having grown up Catholic, I think it's fucking hilarious
The Lonely Island is hilarious, at first I didn't care for their newest album but it grew on me as so many others do, so much so that I like it more than the last one. "No Homo" is a really funny one, check it out if you haven't heard it.