The position of Hasso Krull in the Estonian literary landscape is somewhat paradoxical. Although he has already achieved the status of a classic, his critical texts keep emphasizing that an author needs to be selfless and impersonal. Hence the philosophical basis of his texts seems, among other things, to harbour a trickster who constantly keeps creating and revoking his own creation. The article is an attempt to analyse the opposite poles in the criticism and poetry by Hasso Krull. His critical texts reveal an interdependece of contrasting concepts, e.g. singularity and plurality. Krull’s criticism is dialogical in essence, attempting to capture both the individual and the general. Poetry, however, enables a much more universal mobility between different levels of language and text. To Krull, poetry appears as a process, developed with an aim to capture a semantic multitude. His poems enjoy testing the boundaries of language, being basically indeterminate. Different interpretations are simultaneously valid and it should be impossible to make out a singular authorial voice. And yet this pursuit of semantic plurality has taken Krull not only further than himself, but has also defined his own image. Thus, his oeuvre serves as a fine illustration of the developments in the Estonian literary landscape over recent decades, inviting – like Charles Augustin Sainte-Beuve – to redefine what is a classic.