I obsessively read I, Cringely when I was in college in the late 90s. It was the Stratechery of its time, and taught me an immense amount about the tech business.
At any rate, none of those exactly fit the bill, because Cringely's two "Nerds" documentaries† hold a special place in popular tech reporting history.
† https://youtu.be/sX5g0kidk3Y † https://youtu.be/Pk2BWphDfvc
For a while he did a series of columns exposing the decline and mismanagement at IBM; he eventually turned these into an ebook that I purchased and thought was a reasonably interesting read.
More recently he had cataract surgery and had to move to a new home after his old one was damaged in the California wildfires.