Sir Gawain and the Green Knight is a complex Arthurian verse romance that features a beheading game coupled with parallel temptation and hunting scenes. These elements are intertwined; yet this is revealed to hero and reader only towards the end of the narrative. The Gawain-poet presents the reader with ambivalent characters and a hero who does not necessarily comprehend the implications of events unfolding around him. The ambivalence permeating the characters has led to manifold, often conflicting, interpretations of the text. The present article explores the characters of Sir Gawain and the Green Knight, in particular the two protagonists, with reference to literary analogues and other works that offer meaningful insights, as well as with due regard to medieval conceptions of art and the values enshrined in Sir Gawain’s pentangle. The objective of the present article is to determine whether the poem’s ambivalent elements give rise to a text that is open-ended, thereby transgressing medieval conceptions of art, or whether the pentangle passage outlining Sir Gawain’s moral code provides a fixed point against which to interpret the unfolding narrative. Other forms of transgression, particularly those pertaining to the boundaries of genre, are also discussed.peer-reviewe