Being free from megacorps let's humans be humans, to express themselves, I love it, the jokes are nice (and are jokes, unlike the nightmare abominations like Clippy and their AIs).
I did too, but I was a child and in retrospect I feel like that made me the target audience.
Like I get that Microsoft has for a long time been trying to make tech and computers feel non threatening. And clippy feels like a reasonable attempt especially within the program it was created for Microsoft Bob which was something I can totally see a world in which it had been popular