When IBM went to the PS/2 architecture, and the OS/2 software, to try to kill the PC clone market and lock up the PC hardware and OS market for themselves, Microsoft was the champion of freedom and openness. Really.
Windows 95 and 98 were when the GUI became cool. Well, cool and available - it was cool on the Mac, but nobody had Macs.
Yeah, I could see how finally getting their GUI system more or less working a decade after everyone else could be seen as cool. And yes, keeping the corporate drone market away from a technically better product, also cool.
"After everyone else"? Well, there was the Mac. And there was TopView. And there was... who, exactly, is "everyone else"? There were workstations like Silicon Graphics, but they didn't even pretend to be available (affordable) for the average user. They weren't competition for the PC. On commodity hardware, it was Windows and TopView, and TopView was... not very useful, to put it charitably.
The PS/2 was a technically better product. It was also IBM's attempt to put the genie back in the bottle, so that it could sell hardware at prices considerably above the commodity level. Technically better? Cool. Not having to pay several hundred dollars more for your hardware? The market thought that was even more cool.
Despite what people around here (including me) might think, when you have the Rolling Stones advertising for you and people are lining up to buy your product at midnight, you're pretty cool.
People forget that Microsoft sold more copies of Xenix (A UNIX operating system) for both PDP-11 and PCs than all the other Unix boxen suppliers of that era. But then marketing decided that they didn't need a real OS, so they sold it SCO and then later bankrolled them into suing Linux suppliers, etc. That was all Steve Ballmer's watch, during which MS shares also lost half their value.
The thing is that Microsoft could not corner the market with Xenix the same way it could with DOS and Windows. They wanted a monopoly they could abuse.
Windows 95 and 98 were when the GUI became cool. Well, cool and available - it was cool on the Mac, but nobody had Macs.