The final time I cried during the Iliad is when Priam begs Achilles in the final book, as seen above.
I've tried to read the Iliad three or four times, going not much further than Book 2 and almost always getting bogged down in that damn list of ships. I probably wouldn't have tried to read it again, if not for Christopher Logue's War Music and Alice Oswald's poem Memorial - both based on the Iliad and both wonderful. This time I've listened to Stanley Lombardo reading his version, while driving to and from work. And if you could categorise devastating depictions of war and death as enjoyable, then I enjoyed it very much: sniffling and weeping my way down St Georges Road; unable to get out of my car in the Woolworth's car park before Andromache finds out the terrible news; attempting to argue with Zeus at traffic lights. I'm not sure I want to read it or listen to it again, but I'm very glad I did.