The elephant in the room when it comes to urban novels. The masterwork used the structure of the Homeric Odyssey as a contrast to the lives of the Dublin working class. The entire work takes place during Dublin's “dailiest day possible,” Thursday, 16 June 1904. The bleak lives of the Dublin working class formed a stark contrast to the heroic Odyssey, and Joyce's frank realism was too avant-garde for the cultural police of the day. From the first installment in 1918, censorship issues dogged Ulysses, eventually forcing a halt to its serialization in 1920. The first editors Margaret Anderson and Jane Heap were convicted in New York of publishing obscenity. Ulysses was subsequently banned in the U.S. until 1933, but copies often trickled in clandestinely as its suppression and subsequent publicity assured a wider demand for what was originally a relatively obscure avant-garde text.

Ulysses' convoluted publication history eventually obscured the author's intent: no definitive version of the text exists. The textual complexities have fueled a vast amount of scholarship. Joyce joked that Ulysses should "give Universities something to work on well into the next century."

With the 1992 copyright expiration, there has been yet another explosion in Joycean scholarship and controversy. Whatever its other effects, the censorship battle over Ulysses certainly played a significant role in establishing its literary status. Along with the appearance of T.S. Eliot's The Wasteland in 1922, the publication of Ulysses signaled the peak year of modernism, and became the icon of a new literary era.

During his self-imposed exile, he was teaching at the Berlitz school in Trieste. One of his students was Ettore Schmitz, better known by the pseudonym Italo Svevo. They met in 1907 and became lasting friends and mutual critics. Schmitz was a Catholic of Jewish origin and became a primary model for Leopold Bloom; most of the details about the Jewish faith in Ulysses came from Schmitz's responses to queries from Joyce. In return, Joyce helped Svevo to find a publisher in France, which propelled his previously overseen masterpiece "Zeno's conscience" to new heights.