How far back in time could I go and still be understood

That’s an important point I like to bring up in these sorts of threads. There is a LOT that two people can do to help or hinder mutual intelligibility.

Yes. But pronunciation and meanings and usage of words can change dramatically over the years.

To take a couple of famous examples.

Duke of Wellington on Waterloo

Or Charles II on St Paul’s Cathedral.

What they meant is left as an exersize to the reader. No they don’t mean what they do today.

Here is someone reading the Lord’s Prayer in Old English; the text is also in Old English with notations made on screen during the reading.

Great post, above and beyond.

“Rice” is fascinating.

So is “sell”–>“give.”

Yeah, pretty much, and traveling a hundred miles would bring in a new dialect. But you’d figure it out pretty quick, and anyone but peasants would understand you just have a off dialect.

The Lord’s Prayer is not the best example since it exists today with many archaic phrases in it.

In case my OP wasn’t clear, to re-phrase, let’s suppose my goal was to “step out of the time machine” and start a conversation and be understood. To that end, I can study any current spoken language to help me along. Having made the effort, how far back could I go in time and have a reasonable expectation of being understood?

I would study Dutch and Icelandic and Italian.

Dutch: The closest extant relative of Old English (other than English).
Icelandic: The closest extant relative of Old Norse (a major influence on English after the Viking invasions).
Italian: The closest extant relative to Latin. The Learned classes would know Latin.

Depends on which translation you’re using:

My personal favorite translation is this (you’ll have to scroll down):

Thanks, that’s more of what I was looking for. Apologies if my OP was unclear.