Both Sydney Owenson and James Joyce illustrate my semiotic theory of iconic realism in their depictions of the strength of women from 1819 to 1919 to 2019. Sydney Owenson’s unique methodology of creating romance out of stagnation in her national tales educates other women in their struggle for autonomy by bringing awareness of cultural disparity in the mid-nineteenth century. She motivates her readers to consider an innovative approach to the nineteenth century male and female dynamic by using specific rhetorical configurations to create discourse between her characters. Likewise, James Joyce illustrates parochial dissonance by means of Victorian feminine perceptions throughout Molly Bloom’s soliloquy in the final chapter of his epic tale, Ulysses. Using stream of consciousness, Joyce leads his audience to the entrance of the sphere of Molly’s mind, taking the reader to every crevice of her feminine consciousness, defying the social stigma of women during this era through Molly Bloom’s expression of unique feminine defiance of human weakness. Thus, Owenson’s national characters and Joyce’s Molly Bloom could be analogous to a linguistic duet that resonates with the harmonics of psychological and cultural discovery through the experience of historical dissonance. They place their iconic characterizations in situations that may have seemed outrageous to their first readers, ah, but not to the twenty-first century’s enlightened consciousness.