Celebrating 20 years of impactful design, Debbie Millman chats with renowned illustrators Brian Rea, Maira Kalman, Barry Blitt, Edel Rodriguez, and Christoph Niemann. Brian shares his journey from collage to narrative-driven storytelling, while Maira reflects on the spontaneity that fuels her work, including her beloved dog. Barry discusses the humor in political satire, and Edel reveals the process behind his provocative magazine covers. Christoph emphasizes the essence of concept-driven illustration and how limitations can spark extraordinary creativity.