If you want to focus on stuff from the 1980's, the ALF cartoon show (and it's spin-off, ALF Tales) is one of the weirdest things I've ever seen. Kids would not even understand 90% of the jokes.
Just to set the stage, the ALF cartoon is about ALF's life before his planet blew up. Meaning you tune in with the knowledge that all the lovable goofs we see in ALF's life will one day be incinerated by nuclear war. This show was popular enough to spawn a spinoff, wherein the characters from the original cartoon were cast in fairy tales. As if this wasn't esoteric enough, each episode was also a parody of something else in pop culture. Just as an example, one episode was about ALF as Jack in the Beanstalk as Norman Bates from the movie Psycho.
It also produced one of the most cringe-inducing examples of white people being clueless about rap music, in the episode entitled "Rap-Punzel" (see what they did there?).
It's on HuluPlus. Here's a link: http://www.hulu.com/...386672#i0,p5,d0
Here are some images so you get some idea of what I'm talking about. (Yes, that is Ronald Reagan as an ALF creature in the last picture)