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The play premiered in May 1992 in Cambridge, Massachusetts as the first production of Mamet's new Back Bay Theater Company. The premiere featured William H. Macy as John, a "smug, pompous, insufferable man whose power over academic lives he unconsciously abuses." Rebecca Pidgeon played the female lead, Carol, described by one critic as, "Mamet's most fully realized female character ... a mousy, confused cipher" whose failure to comprehend concepts and precepts presented in John's class motivated her appeal for personal instruction. 
In October, a year after the Anita Hill - Clarence Thomas hearings which "crystallized and concretized" Mamet's dramatization, it appeared off-Broadway at New York City's Orpheum Theatre, with Macy and Pidgeon reprising their roles. The production included a rewritten third scene. Critic Frank Rich provides a summary of the play in his review of the off-Broadway production:
- Oleanna ... is an impassioned response to the Thomas hearings. As if ripped right from the typewriter, it could not be more direct in its technique or more incendiary in its ambitions. In Act I, Mr. Mamet locks one man and one woman in an office where, depending on one's point of view, an act of sexual harassment does or does not occur. In Act II, the antagonists, a middle-aged university professor and an undergraduate student, return to the scene of the alleged crime to try to settle their case without benefit of counsel, surrogates or, at times, common sense.
- The result? During the pause for breath that separates the two scenes of Mr. Mamet's no-holds-barred second act, the audience seemed to be squirming and hyperventilating en masse, so nervous was the laughter and the low rumble of chatter that wafted through the house. The ensuing denouement, which raised the drama's stakes still higher, does nothing to alter the impression that "Oleanna" is likely to provoke more arguments than any play this year.
It had its London premiere at the Royal Court Theatre in 1993, directed by Harold Pinter. David Suchet played John (in a Variety Club Award-winning performance), and Lia Williams played Carol, in a version that used Mamet's original ending from the Cambridge production. As Pinter notes in personal correspondence to Mamet that Pinter also published on his website:
- There can be no tougher or more unflinching play than Oleanna. The original ending is, brilliantly, "the last twist of the knife." She gets up from the floor ("Don't worry about me. I'm alright") and goes straight for the throat. The last line seems to me the perfect summation of the play. It's dramatic ice.
Michael Billington, in a review published in The Guardian, endorsed Pinter's choice of ending, saying "by restoring Mamet's original ending, in which the professor is forced to confess his failings, Pinter also brings out the pain and tragedy of the situation."