If I had a time machine, how far back could I go and still be able to carry on a conversation with people in England?

by Skwink

How far back into the past could I, an American with a very good grasp on Modern English, carry on a normal conversation with an Englishman?

Would I be able to better communicate with my English knowledge with say, a king of England, than with an average Peasant?

true_new_troll

This is one of the more popular questions for this subreddit. Here is an answer by /u/texpeare found in the FAQ.

Uh oh, I see that the first link is dead now for the example of Early Modern English (~1500). Here's another example that hopefully won't be taken down: https://www.youtube.com/watch?v=qYiYd9RcK5M