I grew up on MTV and Vh1... back when they played music videos all day. This is the one that was usually considered the greatest:
But personally I used to love this one when I was a kid:
And another one of my personal favorites was the little milk carton adventure for Coffee & TV
One of the more recent videos I really love, because it was just crazy is this one:
It's been a while since a music video was able to be groundbreaking, raise a lot of eyebrows, and take sex in a new place. For me this is the current reigning champ.