Since a winter morning in 1971 when a teacher wheeled a teletype into his classroom to debut a game about the Oregon Trail, people have been telling interactive stories on digital platforms. From text adventures to VR poetry, MUDS to mobile romance sims, and chatbots to roguelikes, these games without graphics have pioneered new techniques for interactive storytelling, engaged imaginations with clever engines and beautiful prose, and explored the new terrain of fiction you can play. 50 Years of Text Games: From Oregon Trail to AI Dungeon picks one text-based game from each year between 1971 and 2020 and studies how it works, what it's about, why it's special, and its lasting legacy. From famous classics to overlooked gems, from personal stories to million-word epics, and from games printed by teletypes to games downloaded on smart watches, this is the fascinating story of interactive fiction's first half-century.