Ben Crystal

their names now, but they're a father and son very well first in early modern pronunciation.

Ben Crystal and I think David

Crystal.

These are the

More on why this is the case in the bonus facts section in just a little bit.

If you want to hear OP for yourself, check out this great video by David and Ben Crystal where they demonstrate the accent and briefly discuss how linguists know reasonably well how Shakespeare and those performing his plays talked.

But to conclude, while certainly there are many words you and a person from this era would trip each other up on, at this point in history you'd have little trouble communicating at a mostly conversational level.

Thus, as long as you didn't set your time circuits for too far before the 16th century, you'd be reasonably fluent in the English of the age, leaving culture shock to be the bigger problem, such as the extreme racism, sexism, religious extremism, rampant disease, poor hygiene, and many other problems of the time.