One writer perceptively suggests that the term "Oleanna" was used to describe swampland being sold as prime real estate.
I think the primary context in which the title "Oleanna" is to be understood appears in a "folk" stanza preceding Mamet's published edition of the play:
"Oh to be in 'Oleanna,'/ That's where I would rather be,/ Than be bound in Norway/ And drag the chains of slavery."
And so, Oleanna is a version of a Utopian promised land, and in the context of the play, the gateway to this better tomorrow is through the halls of Academia. Susan, the victim of her own false expectations of how the university is to transform her existence, repeatedly mentions the struggle she had to endure in order to get into college. For her, academic success is central to her vision of a better life. John, the pedantic professor, also sees Academia as the means to a comfortable, upper middle class existence with his new house, wife, and son. All he needs to do is make tenure, and his future is secured.
However, John presents himself as an academic bad-boy who debunks the very Academia with which he is trying to secure his comfortable future. This ridicule of the academic process strikes at the heart of Carol's dreams of a better future through education. She quite rightly sees that the professor is trying to have it both ways--playing the academic outsider while trying to kiss-up to the tenure committee in order to ensure his cushy new home in the suburbs. When someone's dreams are threatened, they become angry and strike out, however they can.
This is a brilliant movie. Anyone working in a high school or university, and anyone contemplating an academic career, needs to watch it, and allow it to soak deep into the structure of the brain. Perhaps that academic career isn't such a good idea, after all. Maybe that utopian real estate is really swampland. At any rate, one needs to be very, very careful when dealing with students.
