It's always been a puzzle to me why some screen adaptations of stage plays work just fine and others fail miserably. Lately, I've been watching a fair number of them--not for the sole purpose of answering that question, mind you: it just seems to have worked out that way. Good thing, too, that I haven't been hellbent on resolving that issue, because I'm no closer to an answer now than I've ever been.
Sure you can talk about how successfully the play has been "opened up" for the screen. In the case of OLEANNA, the answer would be "not very much at all." It is, as others have noted, still very much stagebound. Like the female student, we feel virtually confined to the professor's office. Theatergoers have to accept such conventions as a (usually) necessary theatrical limitation. But in the context of a film, it becomes almost unbearably claustrophobic.
And I see from reading other reviewers' comments, that I'm hardly alone in finding the dialog too mannered. For long stretches at a time, the two protagonists (well, actually, antagonists) do nothing by interrupt each other. Some interruption makes for a more natural representation of actual conversation, but when neither character actually gets to complete an entire sentence, it is anything but natural. It's just irritating. Mamet, who reportedly writes to a metronome, should probably have turned the darn thing off this time out.
And of course there's that constantly ringing telephone. That would likely have driven me nuts even as a theatrical device. On film it's too much.
Mamet is always interesting enough to make almost any of his projects worth watching (at least once). And William H. Macy is his reliably quirky self. The quintessential character actor, he shines when given the lead role. Despite the mannered dialog, he is able to plumb his character's proverbial depths and create a fascinating portrait of a tortured academic, whose ambition, though very real, is hampered by nagging self-doubt (to say nothing of his doubts regarding his chosen profession).
Debra Eisenstadt as his student antagonist doesn't have as rich a palette to work with. Her character goes from insecure, diffident student, somewhat in awe of her brilliant professor, to near militant, bent on the personal destruction of her former instructor. The actual transition seems to have been made deliberately vague. She seems to have fallen under the influence of an unidentified but apparently quite militant "group" and finds some new strength and a sense of identity therein. With a moral certitude unique to the very young, she has no qualms about sacrificing her professor's life and career on the altar of "political correctness."
Which brings up the subject of the film's "message." The film's tagline is "Whatever side you take, you're wrong." And that simply is not true. As riddled with self-doubt as the professor is, he is clearly the more sympathetic character. Yes, both "sides" are aired, but it is clear almost as soon as the nature of the conflict is articulated, that the tortured but intellectually honest professor doesn't stand a chance against the newfound black-and-white worldview of the "true believer" student.
All of this conflict could have made for gripping cinema. What you actually are likely to come away with is that "hmmm-it-probably-worked-onstage" feeling. And that's too bad. Given the potentially incendiary subject matter, it really should have been a better film.