- Critical Dissonance: Regarded as one of the most important novels of the 20th Century by critics and literary scholars, but lots of general readers find it difficult to get through.
- Epileptic Trees: There are numerous fan theories about the identity of the mysterious man in the brown macintosh, and some of them are downright bizarre. Some have suggested that he's God, Satan, the Grim Reaper, Hermes, the ghost of Leopold's father, or possibly just one of the many minor characters mentioned in various other chapters. Vladimir Nabokov speculated that it's James Joyce making a Creator Cameo.
- Harsher in Hindsight: At one point during the extended dream sequence in "Circe", Bloom is accused of sexual harassment by various female acquaintances in a surreal courtroom sequence. After one woman shares her stories about his lecherous behavior, several other women jump up and shout "Me too!" while brandishing dirty letters that he sent them.
- Hilarious in Hindsight:
- The unnamed narrator of "Cyclops", who hangs out with uber-patriotic Irish nationalists, likes to claim (perhaps sarcastically) that every single important figure in human history (including Shakespeare, Dante, and Benjamin Franklin) was actually an Irishman. Not unlike a certain Russian Starfleet officer.
- Zero Mostel played Leopold Bloom in Ulysses in Nighttown, a stage play based on "Circe". He later went on to star in Mel Brooks' The Producers opposite another character named "Leo Bloom".
- True Art Is Incomprehensible: Or at least difficult as hell for the unprepared.
- Special mentions for Proteus, Oxen of the Sun, and Penelope. Dear God, Penelope.
- Values Dissonance: We never learn exactly how old Edy Boardman, Cissy Caffrey and Gertie MacDowell are—but considering Edy has a younger brother who's still a toddler, it's very likely that they're younger than 17. Ulysses was written when the age of consent in Ireland was still 16, and the story takes place around 30 years after it was raised from 13. At the time, readers probably objected more to the voyeurism and masturbation in "Nausicaa" than to the fact that Leopold Bloom was (possibly) masturbating to an underaged girl.
- The narration admits that 'Gerty would never see seventeen again', so she's not underage (Edy and Cissy might be, though).
- Values Resonance: The book was written in the early 1920s, but its frank portrayal of antisemitism and Irish nationalism would seem a lot more timely in the wake of the Holocaust and the Irish Civil War in the ensuing years. Notably, the latter began just a few months after the book was published.
- The Woobie: Bloom and Dedalus, though in different ways. With Stephen it's a bit more obvious if you've read 'Portrait of the Artist', where he seems more of a failure. Bloom has it bad too, between having a dead father and son, being a Jew at a highly anti-semitic period in Ireland and generally being an outcast to most of the citizens.
YMMV / Ulysses