X-posted from Ask Reddit: As an English speaker, how long into the past would I have to go before I couldn't converse with an Englishman?

by RegalPlatypus

That is, before we couldn't communicate effectively (through spoken english)?

Hotblack_Desiato_

From the FAQ. TL;DR, around the early 1500s, though things would still be a bit weird by the mid-late 1500s.

The first video link, with the 1500-1600 pronounciation, is dead, and I don't remember what exactly it was, but this is very similar.