This is a tremendously broad topic, but perhaps with the linguistic liberty of this forum - in terms of its ability to branch out using translations - it would be rather interesting to discuss a little certain works from differing genres. I'm always on the look-out for various translations on different writers, but it's been some time since I've had the time to sit down with the classics (ordinarily, I spend my time with much later historical and modern texts, both fiction and non-fiction).
I've read a few of Martial's epigrams as well as Juvenal's 10th Satire (and a little of his 7th) in the Latin, of which the latter satirist was especially difficult, given the vocabulary, references, etc. It was a bit disheartening, but with those sorts of crude and snarky comments of his, I think it's worth it; translations can often too easily either under- or over-exaggerate his vulgarity, or else be unable to transfer some of the nuances over to the English. It'd be fascinating to hear some of everyone's views: any particular preferred satirist?