Back in the 1990s, we started work on pedagogical agents — a novel paradigm for interactive learning. Pedagogical agents are autonomous characters that inhabit learning environments to engage with learners in rich, face‐to‐face interactions. Building on this work, in 2000, together with our colleague Jeff Rickel, we published an article on pedagogical agents (Johnson, Rickel, and Lester 2000) that surveyed and discussed the potential of this new paradigm. We made the case that pedagogical agents that interact with learners in natural, lifelike ways can help learning environments achieve improved learning outcomes. This article has been widely cited, and was a winner of the 2017 IFAAMAS Award for Influential Papers in Autonomous Agents and Multiagent Systems.1 On the occasion of receiving the IFAAMAS award, and after 20 years of work on pedagogical agents, we take another look at the future of the field. We start by revisiting the predictions we made in 2000 for pedagogical agents, and examine which predictions panned out. Then, informed by what we have learned since then, we take another look at emerging trends and reexamine the future of pedagogical agents. Advances in natural language dialogue, affective computing, machine learning, virtual environments, and robotics are making possible even more lifelike and effective pedagogical agents, with potentially profound effects on the way people learn.