Yes, I had pirated copies of Windows 3.1, 3.11, 95, 98, ME, XP and now run Windows 7 Home Premium upgraded from the Windows 7 Starter that came with the laptop with a key given to me over MSN, so I suppose that should count as pirated too.
I think I did purchase Windows 95 at one point in time when I was at university, as I thought there was something wrong with my copied CD (turns out there wasn't - I just had the junkie virus in my bootblock so it was still there after reformatting).
I bought Mac OS X 10.3, 10.5 and most recently 10.6 Snow Leopard, as well as Amiga OS 3.5, 3.9 and Morphos 2.x.