Total Entertainment Forever by Father John Misty
Macauley Culkin as Kurt Cobain, and a broad parody of the Heart Shaped Box video (among any number of other things) is genius. I suspect Cobain himself would have found it hilarious.
Music videos peaked in 2000. It went all downhill after that. It was actually the start of showcasing the artist in their danceathons. Horrible.
Some great videos I remember. Alicia Silverstone had several cameos in Aerosmith videos. All great. She got more attention than Steven Tyler's own daughter.