In life, ambiguity frustrates us. In poetry, it delights us. In drama? As long as we are reading a masterpiece that allows for multiple interpretations, we perceive ambiguity as richness. Uncertainty intrigues us. But, how does one stage the ambiguity we perceive in Shakespeare’s characters, in the plots of his masterpieces, in his half-closures, in his brilliant puns? We’ve seen very different King Lears, Hamlets and Iagos, all of whom said the same words. A Midsummer Night’s Dream is not always funny and The Winter’s Tale can be quite bitter, despite its “happy ending.” This lecture explores the tension between text and theater caused by Shakespeare’s ambiguity.