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Bring on the tough stuff - there’s not just one right answer.
What do you think prompts the speaker to start thinking about his own death? For the first twenty or so stanzas, he's cheerfully thinking about the dead villagers. What shifts, and why?
Why do you think Gray uses so much personification? Why, for example, does he say "Let not Ambition mock their useful toil" in line 29, instead of, "Hey, ambitious people, don't make fun of these guys"? What's the effect on your reading?
In his Preface to Lyrical Ballads (which you can access here), William Wordsworth famously used Thomas Gray as an example of what poets should not do. He said that Gray used too much of what he called "unnatural" language—too many metaphors, too many personifications. Wordsworth argued that regular people didn't really talk like that, so poets shouldn't, either. Do you agree with Wordsworth? Why or why not? See if you can use examples from the poem to explain your answer.
Who do you think is the intended audience of this poem? Men, women? Rich people, poor people? Young or old? Why do you think so?
If this is an "Elegy," or a poem of mourning, who or what is it mourning? How do you know?
Why do you think Gray insisted so much on the fact that it's a country churchyard? Would the poem be different if it were set in a city? How so?
What do you imagine people will say about you after you're dead? What would you like them to say? If you could write your own epitaph, as Gray does in this poem, what would it say?