This study is a three-part play of musement on a few details in the potentially infinite landscape of Umberto Eco’s turn to, relations with, and adaptations of Pragmatism. This three-part guess was product of an abandoned first guess-attempt entitled: “Who’s on First(ness)?” The present title ensued naturally, and with some laughter, in recalling and using the play on words and names made famous by Abbott and Costello. Section 1 will mention two uncles of American Pragmatism. Section 2 will engage in Eco’s ista ricostruzionista (with a dash of ologo) reading of “iconismo primario” (primary iconism) that raises questions regarding his Peircean rereading and assessments. Section 3 will switch to a darker voice and touch upon a few issues in Eco’s writing (or not) on the “comic,” particularly his essays “Pirandello Ridens,” and “The Comic and the Rule.”