How far back in time can you understand English?

Eddie Izzard speaking old English to a Frisian farmer:

https://youtu.be/OeC1yAaWG34?si=lkoQ--uZNN8Ntpqy

As a Norwegian who speaks English and school-German, Dutch is fairly easy to read but sounds like you're speaking a mix of English, Norse and German with a mouthful of gravel (similar to the Danish, who Norwegians like to say speaks Norwegian with a potato in their mouth)

As a native English speaker who also knows some German and has studied some Anglo-Saxon... I'd say the High German sound shift can really mess up hearing Anglo-Saxon for German speakers but reading it is easier than it might be for a modern English speaker...

The orthography of Anglo-Saxon can make it look easier to read for a modern German or Dutch speaker, but to actually hear it could be confusing. Specifically around the words written with the past tense marker "ge" -- or other words using "ge", which is pronounced like modern English "ye" (hence English 'yester[day]' instead of German 'gestern'), not hard "ge" like in modern high German.

And yes Dutch (or modern Low Saxon dialects or Frisian) could be closer but the orthography is very different and also Anglo-Saxon had a palette closer to the front of the mouth than the back like Dutch.

Also other West Germanic (and North) languages lost the dental fricatives ("thorn" (þ) and "eth" (ð)) while English (and Icelandic) kept it. And Anglo Saxon used them heavily. Old Franconian and Old Saxon had this sound, too, but lost it (hence "the" vs der/die/das etc)

Reading it vs hearing is deceiving. The orthography shifted markedly after the Norman invasion when French speaking elites imposed a continental Romance / French language spelling system over top of the ordinary people's Germanic language. In actual spoken language there was likely far more continuity, we just don't have good records of it because the ruling elite was disdainful of English and used French at the court.

So someone who is a modern German or Dutch speaker will have an easier time reading Anglo-Saxon than an English speaker, perhaps. But that's a bit deceiving. Many of the sounds written there had a very different spoken sound than their modern German or Dutch counterparts, and are actually closer to their modern English variants. (ge in particular pronounced "ye" not hard-g, so words like yesterday were spelled with "gest" similar to modern German, but not spoken that way at all).

Simon Roper on YouTube does a better job of this recently: https://www.youtube.com/watch?v=842OX2_vCic

That seems to me like a really worthwhile effort, especially for the continental Europeans if they want to keep the EU alive, even if it needs major, structural reform that I am not confident it can implement without total deconstruction first. If the EU wants to survive it simply cannot allow English to dominate it, nor is even French ideal, making Dutch the official language is of course silly for obvious reasons (regardless of my affinity for it), contemporary German seems to be self-deleting in many different way for many different reasons, and nonsense like Esperanto speaks for itself. But a kind of merging or integration of the German languages of central Europe would be an ideal candidate to bring about European unity in a sustainable and healthy manner... a meeting in the middle, maybe a restoration of old high German even that is the common node.

I am generally even just sad writing this because even my proposal invariably means the total destruction of many languages, traditions, cultures, and true and healthy diversity that has defined Europe over all of recorded history; but at least if this effort of trying to mash Europe into a kind of neo-communist of uniform sludge, at least try to create something new and beautiful out of it, not some disgusting brown mush where the non-english EU speaks English, while by the end of the century the majority of people will not even be indigenous Europeans anymore.

It is sad realizing that what we are all currently witness to is a cataclysmic collapse and destruction of civilization in Europe on an order that humanity has not witness since the civilizational collapse of the Americas or even the Bronze Age collapse and minor cultural collapses and ethnocides that were perpetrated through the French proto-communist Revolution, the Russian communist revolution and the Chinese communist revolutions. It is astonishing knowing that I am living through a historical event that may even never be recorded, let alone well, because the likelihood that it will be recorded at all, let alone accurately is very low.

If a common German language could be created, along with maybe a common Romance language for Hispania and Italy, etc. at least there would be a kind of remaining legacy akin to how the Egyptian icons are enigmatic, even if their culture did not survive.

And yet we manage it with speaking. This is why I call it brain damage. It's like trying to explain red to a blind woman.