We will start with this hunk, the reason this entry was created: Elvis Costello, singing Oliver's Army.
I perfectly understand, but still am puzzled; How can the ability to pick musical notes in an unbelievingly beautiful way and the utter cluelessness of how retarded he looks co-exist in a single person? But that is what we nerds are about (Costello is arguably the world's first nerd rocker). According to the Oxford Dictionary, the word 'nerd' evolved from the Latin version of the word 'unbalanced'. True.
The next: Kate Bush, singing and dancing to Wuthering height.
Admittedly, her videos are not awful; they all walk the fine line between clunkiness and classic art, but always tilt one step towards the former. Probably she does it intentionally and I cannot help feeling sympathy toward the director of the video.
Time is running out, so to be continued…
P.S. Shashank put this in his weekly newsletter. The greatest music video ever produced (without music).