This essay is on the trail for the traces of Joyce`s mourning for his dead mother in Stephen`s disquisition on Hamlet in the “Scylla and Charybdis” episode of Ulysses. Joyce`s emotional distress arising from May Joyce`s death in 1903 has attracted little critical attention. Joyce`s antipathy against Catholicism has been a frame of reference expounding Stephen`s recoiling at his Catholic mother and, therefore, Joyce`s nonchalance about the loss of his supportive mother. Diverging from the socio-political view of Joyce`s coldness towards his mother, this essay argues that Stephen`s Hamlet lecture in “Scylla and Charybdis” is no less than Joyce`s mourning for his long-dead mother by way of projecting his melancholy onto Hamlet`s sorrow for his deceased father. Joyce`s grief over his deceased mother is further traced back to his 1904 narrative essay “A Portrait of the Artist” written a year after his mother`s death. The 1904 essay mainly predicates his rationales for his will to artistic freedom, but his odd reference to an unidentified man`s sorrow in the essay alludes to his unresolved attachment to his dead mother. In “Scylla and Charybdis,” Stephen`s grieving memory of his dead mother is certainly a psychopathological symptom of Joyce as the “Man of Sorrow” mentioned in his 1904 essay, which signifies his unresolved attachment to his bygone mother.