In this paper I will make a claim that laughter in the drama classroom can be healthy, an educational virtue. But it can, of course, also be unhelpful, callous and make life very difficult for teachers. When it works educationally, I am suggesting that there is a strong potential link between the virtues of laughter and the virtues of beauty – or at least a particular aspect of beauty, the virtues we associate with charm being charming. Which of us would not, after all, delight in being called a charming teacher? I will explore these issues by referring briefly to the philosophy of Kant and in particular his theorising of the beautiful and the sublime; to examples of drama teaching drawn from both primary and secondary classrooms; and to examples of popular drama, concluding with Alan Bennett’s The History Boys, a wonderful play, now a film and available on DVD.