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You could go back as far as you like. I've seen movies in ancient egypt, the roman empire and many other older times and places where they spoke perfect english.

Bold of you to assume I communicate effectively now

Several years ago, King Felipe of Spain paid a visit to New Mexico. He later remarked that in his tour of the northern part of the state, he met people who spoke a dialect of Spanish which had last been spoken, in Spain, several centuries ago.

An anecdote about accents and dialects: In the mid-2000s I was part of an event that brought the current world champion pipe band to Pittsburgh PA for a concert. The band was St Lawrence O'Toole, which drew great highland bagpipers from all over Ireland--yes, Ireland. During a reception before the concert, I joined a bunch of the band outside for a smoke. The group was buzzing away in conversation (English, not Gaelic), many of them excited to be State-side for the first time. One of them turned to me and said, "You don't understand a thing we're sayin' do ya?" I shook my head 'no,' and he said, "That's ok, some of us don't understand each other either."

I was kinda amazed that I actually understood the old English phrases. As a native German speaker, that is.

When my father was in college one of his professors read something in "old English" and asked if the class could tell what it was. Dad recognized it immediately. In fact, after the first few words he started saying it along with the prof. It was the Lord's Prayer. Dad grew up in a village in Eastern Europe where Saxon was still spoken.

When my great grandfather came back from the war, he said one thing that really surprised him was just how many different dialects there were from around England.

I was born in Glasgow, but grew up in Canada. In my opinion the most difficult English accent to follow is a working class Glasgow accent. The Liverpool, Newcastle and certain Irish accents are also hard. But an American, Australian or Canadian visiting Glasgow would struggle with a working class Glaswegian speaking at normal speed.

Mate I'm from Northern Ireland and can barely understand people from southern England. Thats a few hundred miles and zero years.

I took Old English (West Saxon dialect) as a linguistic requirement for a Ph.D. degree in English about 30 years ago, & since I used German as my foreign language requirement, if I didn't know the meaning of the word, I substituted a German vocabulary word, & I was correct almost 95 percent of the time.

Back in high school in the USA we had an exchange student from Poland. For her English was tricky but oddly enough we have Spanish classes we take and she excelled at it. She said there were so many similarities between Polish and Spanish. What those similarities were I'm not sure. But within just a couple months she was top of the class and until that point she had never worked with Spanish.

I will never forget my 13 week work trip to the UK. I was working with a Scott, an Irishman and a Londoner who stuttered. I ( the American ) ended up occasionally being the interpreter for the others, they occasionally were incomprehensible to one another, but I seemed to be able to understand all of them. To this day I have no idea why that was the case.

No wonder Yoda talks like he does. He's over 800 years old.

I find it fascinating that I, as a native Swedish speaker, could read that first phrase in old english without much effort.

I saw a linguistic teacher once, and he said that the accent used in southwestern nc, because of its isolated location, was as close to the upper class British accent from the 1800s as a modern person could get.

I've noticed a curious phenomenon. My mother spent a little time in Northern England (Crewe). She told me that she had a heck of a time understanding people there. But when she as asked them whether they understood her, the answer was invariably "yes." Also the same thing happened with some Scottish folks.

What do we want?!

Short answer: You could chat with Shakespeare, but he might have to play translator for you if you wanted to chat with his grandfather.

When it comes to pirates it's important (to a degree) to distinguish between pirates and privateers. Privateers were issued letters of marque during war time and were essentially privatised warships - they could legally "pirate" enemy ships.