This essay is an attempt to read Edgar Allan Poe`s and Wallace Stevens` poetry and poetical theory from the perspective of negativity, which has been mentioned as one of the key concepts in modern aesthetics since Kant`s “negative sublime”. It is interesting that Harold Bloom underrates Poe`s poetry and poetical theory saying that no reader who cares deeply for the best poetry written in English can care greatly for Poe`s verse, while Theodor W. Adorno presents Poe as one of the harbingers of modernism in that both of them agree to place importance on negativity respectively as the main principle of modern art and ``American Negativity``. Especially Poe`s “Nevermore”, the repeated refrain of “The Raven” can be said to express a peculiar moment of “American Negativity” as Emerson`s or Stevens` “Nothing” does in that it functions as some pivot on which the whole structure of a poem turns and contributes to producing new meanings and thoughts, even if it itself has no definite meaning. How various arguments on negativity or negative presentation can help us understand Poe`s and Stevens` poetry and poetical theory newly and how a new genealogy of American poetry from Poe to Stevens can be possible will be examined.