The article is a comparative study of the well-known mythological sujet of the chained hero and another popular motif, that of the labyrinth. The author lists in brief various versions of the legend about the chained hero, widespread in the Caucasian-Near Eastern region, emphasising the most significant details: tracing the motif of theomachy as a sin, and retribution common for all of them. The paper includes the analysis of such features of the chained hero as his ambivalence going back to the archetypal twoness; twins representing a positive character and that of the snake (dragon) nature. Another reason for the ambivalence of the chained hero is his chthonic nature, observable in the place of his imprisonment or his environment. The cave here is approximating to a labyrinth-like covert, and the idea of a labyrinth, in its turn, points to the motif of initiation. The Caucasian-Near Eastern complex of the stories about the chained/neutralised chthonic heroes allows to anew elucidate the cave-labyrinth theme in the vast proto-Caucasian context, and to probably give original interpretations to newly found artefacts depicting respective symbols.