The purpose of this essay is to show that what defines a hero is far more complicated than the prolific author and mythological expert Joseph Campbell would have one believe – in his view, heroic qualities stem from a certain type of chosen individual and reoccurring narrative motifs without taking social structures and masculinity into account. By analyzing the characters Beowulf and Odysseus through a filter, consisting of Campbells model of the “hero’s journey” along with perspectives provided by studies in the masculinity field done by Raewyn Connell and Jørgen Lorentzen together with Claes Ekenstam, this essay concludes, in short, the following: applying Campbells model of the hero does reveal several similarities between the two characters, though it ultimately fails to prove any deeper connection. The aspects brought into focus by utilizing different concepts of masculinity however, proved to be more enlightening, with the most notable conclusion that the various tests forced upon both Beowulf and Odysseus mirror Raewyn Connells concept of “the hegemonic masculinity”, which in essence means that the most elevated masculine qualities existing in the context of the book are also the same ones being targeted by the antagonistic forces present in the story.