Obscurity factor: 10
We all know that the mega-hit The Simpsons started out on Tracey Ullman's first show in the 1980's, but what many people don't remember is that The Simpsons shorts rotated with another series. Dr. Janice N!godatu was a psychotherapist with a calm, pleasant manner that always seemed to find herself in surreal circumstances. Some of those circumstances were very subtle and that gave the shorts a curious, intellectual quality. They were conceived and drawn by well known cartoonist, M.K. Brown. There were six four act shorts, plus two unreleased episodes. These little gems are hard to find now. Here is the first in the series. Dr. N!godatu wears her slippers to the office by mistake. In the second segment watch the plant on the filing cabinet. Also in these clips are classic sketches from the show.
Below is "Freeway" in which Janice goes shopping with her friend Pat. Pat doesn't drive on freeways, through tunnels or on bridges.
These shorts are very hard to find and as far as I can tell, no stand alone video of them exists. The segments above are uploaded to YouTube by TraceyUllman1111. You can find out more about Dr. N!godatu on this page, which has synopses of the episodes and screen shots.
Obscurity factor: 10 (relatively unknown, hard to find)