95 wasn’t bad. 98 had some bugs and they quickly released 98SE, which was great and then they released the soggy turd of windows Millennium.
That was their disaster year. Windows ME, released just 2 years after 98 in 2000, and written out of existence just one year later by Windows XP.
Vista had better features and stuff, but people hated it because it was a huge jump in needing extra resources and any mid tier or lower laptop that came pre-installed with it the first year was underspecced for it, so it ran like turd on those and sucked away gaming performance on everyone’s rig.