From captivating imagery to conversational interactions, generative AI is transforming our world. But how did we get here? This workshop delves into the deep history of AI, revealing the fascinating origins of generative AI and its predecessors. While recent advancements like ChatGPT have sparked discussions about the future, AI's journey stretches back decades, with significant milestones shaping its evolution. For librarians, understanding AI's trajectory is crucial for preparing for its impact on libraries and information literacy education. This workshop equips you to navigate conversations about AI's potential and pitfalls, empowering you to develop future-proof instruction strategies for a changing information landscape. Together we will analyze trends and potential future directions of AI to prepare ourselves for the evolving landscape, discuss how AI will transform higher education and libraries, and brainstorm strategies to adapt and thrive. We will also discover how libraries can leverage AI to enhance information literacy instruction, addressing issues like bias, plagiarism, and critical evaluation of AI-generated content. By exploring the historical and current landscape of AI, participants will gain a deeper understanding of its capabilities and implications for libraries and education, allowing them to prepare for the future with confidence and critical thinking skills. (This session’s title and abstract were written with help from Google Gemini.) Attendees should bring a laptop or any other Internet-connected device they are comfortable typing on - we are planning on actively using LLMs during this session.