This paper focuses on how British colonial institutions adversely affected the male characters in James Joyce`s Dubliners and A Portrait of the Artist as a Young Man. When pressured to conform to societal expectations, characters face a particular crisis related to the stage of life they are experiencing. In childhood, the patriarchal institutions of education and family demand that young boys submit to their authority and they use physical violence and surveillance to assure compliance. As a result of this struggle, young boys in Joyce`s writing experience a crisis of control. The short stories "The Sisters" and "An Encounter" from Dubliners and the beginning of A Portrait of the Artist as a Young Man highlight this crisis. Joyce employs these masculine crises to expose the British colonial system for its oppression of Ireland, and his writing aimed to awaken the Irish people to the reasons for their own subjugation.