I never had a WebTV or MSN TV, but I always liked to watch the stupid infomercial, which I frequently did as a little kid. Then I got a Dreamcast, which had similar technology built in if you used the “internet” disc or whatever (I even had the official Dreamcast keyboard), and I realized how awful the whole experience was in 1999, especially compared to the Windows 98 computer I had in my bedroom, roughly 3 feet from the TV with the Dreamcast.

I do remember in the early 2000s when I was a high school student working at Best Buy, trying to help an older man get a replacement for his WebTV that he had a warranty for. I think we might have still sold an Ultimate TV model for him to get, but I don’t remember the specifics. What I do remember was how much he loved and used that thing, in a way that was fairly shocking to me, given how slow and unoptimized the systems were by then. I’m hoping I was able to convince him to spend his $500 credit or whatever on some eMachines package that would honestly still been a piece of shit, but would have been way better than the primitive low-memory WebTV, but who knows. That man loved that WebTV. That was one of the first times I got to see just how change-averse people can get when it comes to technology, and in retrospect, situations like that one helped me develop empathy for users.