Creativity and innovation are no longer exclusively the province of humans, but the result of collaboration, a game of interpretation in the dialogue between humans and machines. This is the world in which we live today, where artificial intelligence is rapidly evolving and new scenarios are opened. Is AI technology revolutionising the fields of art, design, communication, and marketing, but as regards typography? This research brought Gianpaolo Tucci to discover aesthetic imperfections as a value of uniqueness for each individual representation. This is not a book on typography, but the expression of a point of view, a practical guide, and an investigation on how the integration and ethical use of artificial intelligence will play a fundamental role in modelling this future.