Unlike other pieces of the Shakespeare sonnet sequence mainly dealing with the poet speaker’s putative relationship with an unknown youth, “Sonnet 94” is focused on a group of figures whose moral excellence was defined by William Empson as arousing ‘Confucian’ sentiment. Empson, however, defies the Confucian virtues of these figures: the sonnet, on the one hand, seems to withdraw its admiring tone ironically as it develops into a latter part; on the other, the ethical sentiment the speaker (or Shakespeare) keeps toward the object figures (or the unknown aristocratic youth) sounds so idealistic as to have no realistic value when transplanted into Henry IV and looked upon from the dramatic context of socio-political interaction implied between Falstaff (substituting Shakespeare) and Prince Hal (substituting the aristocratic youth). Taking Hamlet and Timon of Athens as examples, this paper uses in counteractive terms Empson’s interpretive strategy of crossing the genre border between sonnet and drama so as to test its critical relevance. Speeches with moral implications obtain their full didactic qualities when separated from dramatic contexts, whereas, confined within the given contexts, their didactic resonance decreases significantly as they are spoken usually by minor or antagonistic characters. Contrary to Empson’s assumption, “Sonnet 94” seems to have been intended by the Bard as a didactic piece of poetry to stand on its own separate from the world of his drama that depicts the human conflicts in terms hostile enough to keep a Confucian idea of humanity from playing any pivotal role.