And here's the Simon Roper videos acknowledged in the article: "From Old English to Modern American English in One Monologue"
https://www.youtube.com/watch?v=842OX2_vCic (short version:
https://www.youtube.com/watch?v=9_pS3_c6QkI ). This runs forward rather than back in time. However, Roper's "How Far Back Can You Understand Northern English?"
https://www.youtube.com/watch?v=90Zqn9_OQAw does run backwards in time.