Sort of ironic that the Windows 95 aesthetic is simultaneously both comforting and familiar (vaporwave), and full of dread and ennui (Dilbert, Office Space).
Dread and ennui is as much a part of vaporwave as anything else. It's kind of the duality of the hopefulness of the era -- Windows and Mac machines being touted as the precursors of the Ono-Sendai cyberdecks we would all be using -- and the soul-crushing boredom and consumerism.
I think how you view it correlates with how old you were when win95 was in use. I certainly don't have any negative associations with it, just nostalgia, but I was just a kid at the time
