Alan Turing’s empirical test for machine intelligence requires the computer to be a highly proficient improvisational actor with a rich knowledge of human culture. This curious criteria is an indication of why theater is an especially effective artistic medium for exploring Turing’s life and work. Although the new generation of chatbots is calling into question the relevance of the Turing Test as an AI benchmark, playwright John Mighton shows us how Turing’s imitation game provides a novel means for understanding human intelligence—and why it may not be so irrelevant after all.