Developed in the 1960s by Joseph Weizenbaum, ELIZA is arguably among the most influential computer programs ever written. ELIZA – and especially its most famous persona DOCTOR – continues to inspire programmers, wider discussions about AI, and imitations. This original ancestor of all conversa-tional interfaces and chatbots maintains a special fascination for engineers, historians, and philosophers of artificial intelligence (AI) and computing. With its ability to produce human-like responses using a relatively small amount of computer code, ELIZA has paved the way for a multitude of similar programs. These take the form of conversation agents and other human-computer inter-faces that have inspired entire new fields of study within computer science. This paper examines Weizenbaum’s contribution to AI and considers his more critical writings in the context of contemporary developments in generative AI, such as ChatGPT. Examining how ELIZA has been discussed can provide insights into current debates surrounding machine learning and AI.