I LOVED, LOVED, LOVED my Weird Al tapes as a kid. I also agree that his original material and "style parodies" are his best material. While stuff like "Eat It" succeeds as a mildly amusing song parody, Dare to be Stupid is not only funny, but is an original song, yet it's an original song in the style of a specific band. And while it's funny lyrically, it's actually not bad on a musical level either.
While the actual "music" was never my main draw for Al, he and his band are all very solid musicians.
I think it's cool that he has kept the same band for so long. He could probably get other people to do the work for way cheaper, I mean, the "music" isn't Weird Al's selling point, but he has stuck by those guys from the beginning. Class act.
Also, I just wanted to give a shout out to one of my personal Weird Al favorites...."The Biggest Ball of Twine in Minnesota".