||Throughout James Joyce's novels, themes of freedom and entrapment prevail, as characters search for a sense of meaning, often aspiring to Romantic models of selfhood. Stephen Dedalus, in A Portrait of the Artist as a Young Man and later in Ulysses, remains isolated from mainstream society, in pursuit of his vocation or destiny; Joyce's women, specifically Molly Bloom and Gerty MacDowell in Ulysses, desire freedom, but they remain under the pressure of gender norms and expectations; and Leopold Bloom in Ulysses hopes for an ideal world that accepts him and in which normative values may be inverted without repercussion. In my thesis, I use the lens of Friedrich Nietzsche's philosophy in his works Human, All Too Human and Thus Spoke Zarathustra, in which he outlines the characteristics of the "free spirit" and the "Ubermensch," or Overman. I argue that Joyce's characters struggle for a sense of Nietzschean freedom, each with the potential for success, yet they remain held back by history and society. While freedom within Nietzsche's texts remains a complicated aspiration requiring one to break away from past difficulties, Joyce depicts the human limitations on Romantic freedom and the unreality of Nietzsche's Romantic model in mainstream society. Joyce instead provides hope for a different type of freedom for his characters, outside of the Romantic framework. Reading Joyce through a Nietzschean lens emphasizes the limitations on freedom, demonstrating Joyce's critiques of these Romantic, and idealized notions of selfhood.