DOS was rock solid, at least around the era of DR-DOS. DESQView 386 was absolutely stable too. The BBS software I ran on them in those days was a wobbly piece of shit though.
I also recall Borland's Turbo Pascal compiler and the accompanying text-mode IDE being ultra reliable.
After DOS I've used OS/2 which was also extremely stable, although suffered from limited hard- and software availability.
Mac OS X used to be rock solid too in the heydays of the Powerbooks and earlier Intel Macbooks. Every now and then there were hardware design flaws though, and now the quality of both soft- and hardware seems to have taken a tragic turn for the worse.
You still do play Russian roulette whenever you plug a USB device into your computer, see "USB Rubber Ducky".