How far back into your country's history could you go without needing a translator?

I asked this before elsewhere, but I thought it led to some interesting answers.

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I wouldn't be confident going past the 19th century US, personally. English has changed a lot in a short time.
- I feel like you could probably make yourself understood all the way back to the American revolution, but anything slangy would be an absolute mess
  
  Maybe, but I don't think it would be effortless. I would imagine it would be easier for you to understand them than the other way around.

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