Conman said:
"Take On Me" by Aha. I know the retro thing sucks but the video still sets a standard today. Also "Sledgehammer" by Ex-Genesis Peter Gabriel. Both videos were cutting edge stuff then and still look great today.
Take on me is my all time favorite music video. Also, George Harrison's I've Got My mind set on you video was great as well.
As for new videos,
Breaking the habit by linkin Park
Also, cman mentioned eliza dushku in the movie The New Guy in her thread, so it reminded me of the Simple plan video for I'm just a Kid.. oooh shes soo damn hot :!:
Midnight Oil - Beds are Burning, its a simple video, but the song makes it cool.