Obscurity factor: 6
In the 1950's, Jack Benny had a very popular television show and was a huge star from his work on radio and in film. At the time, Warner Brothers were experimenting with making animated versions of television stars - they had already done The Honey Mousers - and his sly, gentle style of comedy translates very well to the medium. In this short, we get to see Jack interact with Rochester, his butler and Mary his fiance, all as animated mice. They make plans to go out and are tricked into going to the Kit Kat Klub, a night club the household cat has set up inside his mouth.
These cartoons are fun examples of an alternate take on the popular culture of the day. The trend continued into the 60's with episodes of shows like The Flintstones featuring Samantha Stevens from Bewitched and, infamously, Ann Margrock. This short is available on the Looney Toons: Golden Collection, Volume 3 DVD.
Obscurity factor: 6 (available on DVD, somewhat forgotten)