Harold and Maude (1971)
Maude (Ruth Gordon)
I had to list them by the films they feature in, because some of them have no character page or the character appears in several (sometimes very different) versions in multiple films. If there is more than one character from the same film, the film appears twice in the list, with different charactors (actors playing them) listed beside the film title.
Discuss the list here: http://www.imdb.com/board/bd0000088/thread/223653701