This is great fun - a story by Colin Gorrie which starts out written in contemporary English, then in the language of 1900, then 1800, 1700, and so on. How far back can you follow it?

https://www.deadlanguagesociety.com/p/how-far-back-in-time-understand-english

How far back in time can you understand English?

An experiment in language change

Dead Language Society
@richardelwes This is great. I was fine through 1500, got through 1400 with a struggle, got about 75% of 1300, and was completely lost at 1200.
@ajsoley Yes similar - I managed to get through 1300 with great effort and was then lost.
@richardelwes I'm obviously a weirdo but only slightly so; I was fine up to 1300, got maybe 85% of 1200, maybe 40% of 1100 and maybe 10% of 1000.