I've always liked bands who display a sense of humor in their music. Warren Zevon and Steely Dan appeal to me largely because they don't take themselves too seriously. But when it comes to the master of comedy in lyrics it has to be Frank Zappa. I listened to his "Apostrophe" album last night and found myself laughing out loud at some of the songs. The lyrics in Cosmik Debris, Uncle Remus and Dinah-Moe-Humm are like a stand-up comedy routine set to music. If you're looking to put a smile on your face, just fire up some of your Zappa collection!
Bowling for Soup is a parody band that rocks. Back in my day I guess Ray Stevens was the Weird Al and there is also Flo and Eddie formerly the front men for The Turtles.
Bob Dylan is another that increasingly over the years often lightens things up a bit in his music with some subtle humor. He often does not seem to take what he saying too seriously anymore, he just says it and lets the cards land where they might.
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