Obscurity factor: 9
This animated series and subsequent special based on L. Frank Baum's characters was produced by Crawley Films, the animation studios that would eventually become Rankin/Bass. In the series, the characters, including Dorothy lived in Oz and went about their daily business, getting into scrapes and general hilarity. The episodes were shorts, running only 5 minutes or so.
Above is an episode entitled Get Out the Vote. Both the Tinman and Scarecrow run for office. The little red man in the hat is a munchkin.
The series led to an hour long television special called Return to Oz. The story is basically a retelling of the original The Wonderful Wizard of Oz with nods to the characters previous history together. The series has yet to be released in DVD, but the special was released on 2006 and can still be found. The episode above was uploaded to YouTube by TheVenerableDrBranio and the opening credits for the special were uploaded by RoyalKidofOz.
Obscurity factor: 9 (Remembered by a small group of fans, otherwise largely forgotten)