In 1954, in an event that was part-literary pilgrimage and part-pub crawl, Envoy founder John Ryan and novelist Brian O'Nolan led writers Anthony Cronin and Patrick Kavanagh, James-Joyce-cousin Tom Joyce, and Registrar of Trinity College AJ Leventhal on a horse-drawn carriage ride through Dublin, Ireland, to recreate the day described in Ulysses now nicknamed "Bloomsday".

Fiftieth Anniversary of Joyce's Bad DateWritten expansively by James Joyce from shorter stories in 1907 to its full publication in 1922, the experimental novel broke new literary ground with its usage of stream of consciousness in narrative and, along with T. S. Eliot's The Waste Land, stood as the pinnacle of Modernist literature in the English language.

Taking place in Dublin on June 16, 1904, the story details a number of point-of- view characters including young writer Stephen Dedalus (who appeared earlier in Joyce's A Portrait of the Artist as a Young Man), Leopold Bloom, his wife Molly, and various Dubliners. While including fantastical events and hallucinations, the narrative largely displays the lives of the average people, complete with difficulties and happiness. Over the course of the story, however, Joyce's overall despondency toward the world is displayed. Dedalus begins his day leaving his apartment over tension with his roommate and ends it accidentally beaten to blindness by an English soldier over a perceived anti-Royalist remark, which is covered up by police. Bloom, who witnessed the crime, determines to believe it never happened and instead continues his day, which he had spent meandering across Dublin, attending a mass, visiting the baths, going to a funeral, attempting to sell an ad, having lunch at a pub, ogling nude statues at the National Museum, dinner at a hotel, another visit to another pub, dropping by the maternity ward, and finally returning home, peeking at various women along the way.

Molly Bloom, however, proved through history as the most provocative character and perhaps the villain, though the protagonist-antagonist standard of literary theory hardly is followed in the piece. Joyce later wrote that he used elements of a girl he dated once (on June 16, 1904), but that the date had gone sour due to a spat over art versus life with him believing her thinking of him merely as a toy. The topic is explored in Ulysses as Molly has an ongoing affair with her manager, "Blazes" Boylan, who is not given a perspective but is displayed as something more pet-like than human. In the final episode of the novel, nicknamed "Molly Bloom's Soliloquy", her stream-of-consciousness is shown as she and her husband retire for the night, concluding with her reflection that he is furniture to their marriage, "a useful hat rack" or "a door".

Scholars to this day debate whether the work is pro- or anti-woman, featuring both vivid and humanistic portrayals of female thought in "Episode 13, Nausicaa" and the conclusion "Episode 18, Penelope" as well as jovial discussions of misogyny in "Episode 16, Eumaeus" and throughout. While on his self-exile to Europe, Joyce married a student from Trieste, Amalia Popper, but fled the marriage to Paris when he took up a week-long invitation from Ezra Pound that became a stay for a lifetime. He came under the patronage of feminist and publisher Harriet Shaw Weaver, who took his female characters as greatly human. After the success of Ulysses, Joyce wrote Finnegans Wake, which he began after a year break and continued unfinished until his death in 1941.

Joyce commented on Ulysses as being "immortal" and that he "put in so many enigmas and puzzles that it will keep the professors busy for centuries arguing over what I meant". However, what gave the work great notice was its perceived obscenity. It had been serialized in The Little Review in the US until 1918, when it came under legal accusation of obscenity due to vividly displaying human sexuality. In the resulting bans in both the US and Britain, the book gained notoriety, surging the readership. Molly Bloom was picked up as a champion among Flappers of the era, inspiring gold-digging and establishing oneself as the dominant role in relationships as a matter of philosophy. Literary minds disagreed whether the portrayal of Molly is negative or positive as a strong figure. Whatever the case, "Mollies" began organizing, disrupting social norms and causing reprisals among conservatives. The Bloomsday celebration in 1954 would soon be joined by numerous latter-generation Mollies, and the festival would spread to dozens of other cities.