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 revolutionizing the fields of art, design, communication, and marketing, but as regards typography? In this era of co-creation, typography as communication technology has yet to be at the center of the scene in this evolution, but it is mature for experimentation. This research brought Gianpaolo Tucci to discover aesthetic imperfections as a value of uniqueness for each individual representation. The world is facing a new era of typographical artifacts, typography that kisses the rigor of the function to embrace new expression values. The synergies between three pillars—time, nature and evolution—delimit its foundations, but the implications of this evolution go far beyond the typography. 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 modeling this future. Take a breath, and as if we were unaware laboratory animals, let’s jump into this journey made of confused, blurred, anatomical, radical, colorful, and sometimes overturned visions.