Obscurity factor: 8
This series based on the work of James Thurber centers on the life of John Monroe (Windom), an absent minded cartoonist for a New York magazine and his wife (Joan Hotchkis) and daughter (Gerritsen). John is good at his work, but he isn't very good at life. He's perpetually distracted by the fantasies that pass through his head and we, as the viewers see his imaginings in the form of neighbors dressed like show girls, amorous school teachers and his own (Thurber's) drawings come to life.
The series ran for a season on NBC and has the distinction of being the first series regular role for Lisa Gerritsen, who would go on to become Bess on the long running Mary Tyler Moore and later on it's spin off, Phillis. Look for Lee Merriweather in the episode, of which part one is above. It was uploaded to YouTube by dentelTV1.
Obscurity factor: 8 (hard to find series, not on DVD, clips and a few episodes available on YouTube)