I did and it was every bit as degrading as you might imagine.

I paid for a ticket to the Windows 7 launch event back in the days. Cost a few euros, in return I got a day of talks, networking, a laptop bag full of sweets and a retail copy of Windows 7 Ultimate. The serial also worked for Windows 10 and 11, so I'd say that was a pretty sweet deal. I honestly cannot say if that technically counts as having paid for Windows though.

I paid once for a full license for Windows 98, not an OEM one that comes with a computer. They then gave free upgrades indefinitely since technically it was always the same computer, so I only needed one copy. Simplified it by avoiding a lot of the pirating crack issues and risks. Every other computer than that desktop has always had Linux, and now it does too since I dont really do much gaming anymore.

Well, Microsoft didn't offer it to you freely....

Mac OS has been free since the 2000s, but I hadn’t paid for it before then either. All the way back to system 7.

I paid for windows 10. Still have the install disk and everything, got it at Fry's RIP.

Heh. Paid for Win 7. Still not ashamed. Best system I had, even if it had it's weird stuff. And it's licence carried on to Win 10 and prolly 11. Cannot say with 11 as I am highly uninterested in it xD