Weird Al's never disappoints (except with ~75% of the tracks on each of his last several albums, but I don't hold that against him).

His hits came fast 'n furious when there was music that make fun of itself so hard....His schtick is dated but he's ingrained in musical satire with all of the greats-

Short List that pops to mind from as many eras I can muster without google:

Rosemary Clooney
Betty Hutton
The Residents
Spinal Tap
Shel Silverstein
Mrs.Alva Miller
Garfunkel and Oats
Tom Lehrer
Jimmy Fallon
Louden Wainwright Jr.
Biff Rose (I cheated)

List goes on but my brain won't...

Fallon kills me with this;
http://videosift.com/video/Neil-Young-Bruce-Springsteen-Whip-My-Hair

If you ever have an opportunity to see him perform live, you should go. He works hard and the two times I've seen him, he did not disappoint. It's a raucous multimedia extravaganza I tell ya!

Couldn't agree more, Playhouse. Saw him live on his "Running with Scissors" tour and has been my second favorite concert so far (#1 was Yes, in-the-round).

And not only did he perform all his greats, run through multiple costume changes, but he also did two of my personal favorites: Yoda and One More Minute. Phenomenal show.

Weird Al almost convinced me that polka is cool. Almost!