“Free association” and the “fundamental rule” are bedrock for psychoanalytic therapy and apply to what both patient and analyst should experience in the process. The article traces Sigmund Freud's revolutionary recognition of the importance of free association that began with his tribute to the works of Ludwig Börne and Friedrich Schiller. The author invokes other proposals akin to free association made by artists and scientists, including John Keats, Charles Dickens, Robert Frost, Thomas S. Kuhn, Arthur Koestler, and Albert Einstein. While emphasizing the importance and the liberatory potential of free association as it relates to effective treatment and discovery, the author contends that there is a “moral press” for both the patient and the analyst to permit free associative thoughts, particularly to question assumptions about how things are supposed to be.