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In this paper, we show Dubliners try to enjoy through music vicarious satisfaction with historical realities and it is Bloomesque insight into them to insulate against “the seductions of music.” Although music itself functions both ways like pharmakon (medicine, poison), Dubliners indulge in its poisonous aspect. In the “Sirens” episode, they like to sing songs to help escape from “loveless, landless, wifeless” realities. Songs such as “M’appari,” and “The Croppy Boy” create sentimental fiction of “other world” and are sung to comfort their frustrations away. They are thrilled and shed tears, ending up shouting for a drink. We can say, however, that the songs come to be added to historical realities without any addition of insight or recovery from frustrations, like masturbation. As long as they continue to indulge in “a sort of group masturbation” as a critic calls it, Dubliners will likely fall into self-destruction or paralysis. Here, Joyce suggests how to help direct out of their self-destructing escapist fantasy as Odysseus navigated out of Sirens’ songs. It is Bloomesque insight into historical realities that insulates himself from it. He only deserves enjoying medicinal aspect of music.