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Bring on the tough stuff - there’s not just one right answer.
Why is Ulysses known as the most influential novel of the 20th century? What is so revolutionary about it?
Can you discern any specific "message" or philosophy from Ulysses? If not, do you think there is some lesson to be learned from the numerous juxtapositions and conflicting philosophies presented in the novel?
Does Ulysses succeed in its goal of elevating the common man or does it come across as literary pandering to lower class people?
Are there any benefits to be gained from the difficulty of Ulysses? How would it be a different book if it were easier?
What do you make of the fact that the people Ulysses is about probably could not understand the book?
How does Ulysses re-work the Odyssey? Thematically, how is it similar to the earlier epic, and how does it challenge and re-evaluate early ideas of Homer's?
What do Leopold Bloom and Stephen Dedalus have to offer one another? In what ways do they form a surrogate father surrogate son pair, and in what ways does the comparison not work?
What is the affect and seeming purpose of the stylistic play in the novel? Is it simply maddening or enthralling or can you discern some reason why Joyce moves through so many different styles?
Why is Stephen such an impossible character? What forces make him feel so isolated from the people around him?
How does Stephen re-work his intense religious beliefs within an artistic framework?
How do Stephen and Bloom address the problem of English oppression in Ireland, and the paired problem of narrow-minded Irish nationalism?
Why would Joyce make the protagonist of his book Jewish? What role does Bloom's Jewishness play in the story?
With a particular focus on Molly Bloom's adultery, what is the relationship between love and sex in the novel?
Why are Stephen and Bloom so passive?
Is Molly's soliloquy at the end of the book a piece of feminist writing or not?
What is the purpose of all the literary references and allusions in the novel? Does it come across as Joyce showing off, or do you think that the allusions actually contribute to the story in some way?
Why is the book so drenched in the particular details of Dublin life? Do these details date it and make it inaccessible to later readers?