The chapter makes a case for Pirandello as the head of an Italian school of fantastic literature that came into being at the end of the nineteenth century. It recounts Pirandello’s use of the fantastic – characteristically without the supernatural – as a tool for distancing himself from the naturalism of the period and as a literary strategy that shared much with the humorism that was likewise dear to Pirandello. Both the fantastic and the humoristic relied on the perception of life’s contrasts to slowly overturn an understanding of the laws of the universe. Focusing on the Stories for a Year, the chapter traces the sometimes uneasy coexistence of the fantastic and humoristic, chronicles Pirandello’s original recreation of fantastic situations and environments in a wholly Sicilian imaginary, and reflects on how the fantastic itself becomes a metaphor for literary creation.