When I read Don Quixote in my lit class, half the book was footnotes so that english readers could get some of the jokes lost in translation.
I also happen to watch a lot of subbed anime, and I've seen(heard) some words translated three or four different ways in one 30 minute episode. And many fansub groups, though unfortunately not the official commercial dub/subs, include translators notes/footnotes to explain interesting problems moving between different languages and different cultures.
Of course, Japanese is a language far removed from English. Italian language films, for all they're from a different language family, are fairly simple to translate into English for the more commercial entertainment.
But on the other hand, reading C.S. Friedman's In Conquest Born, where a great deal of energy is devoted to explaining and demonstrating the complexities of one of the languages, I found that the English versions did perfectly fine without all the paranthetical notes on speech modes.
I write mostly spec fic, and much of that is secondary world fantasy or sf, so I'm constantly driven nuts when I write something that's fantastic in English, only to realize it wouldn't come off so well if I was writing the story in the language the characters would actually be speaking.
Finally, there's the more extreme version of translation woe: localization. At least in the anime fansub community, people rip each other apart over whether or not some fansub was too localized. For example, translating Japanese honorifics into terms like "mister" and "miss". There're a lot of familiarity and respect marking lost between Japanese and English, and it can completely ruin some of the more subtle subtext if it's not dealt with right.