"Mad World" by Tears for Fears. This isn't only a great song that spawned a much better remake (linked below, for fans of Donnie Darko) but the video is so classic 1980's! I mean the dude is singing a sad song, and then another dude starts dancing outside at about the 2 minute mark. So much 80's goodness
In my opinion, here is the better version. It can be heard at the end of Donnie Darko, a great, but strange and dark movie if you like that kind of thng!
(This version is the real reason I am posting... it brings out my emotions)