Worst: DOS / Win 3.11, I just hate it... Single tasking, lousy memory management
Second Worst: Atari TOS, what a joke
Third Worst: Win 9x / ME, unstable, unreliable, needs to be reinstalled every 2 or 3 months, huge.
Best: AmigaOS 3.x, fast, nice to work with, easy, configurable.
Second Best: Mac OS X, easy to use, beautiful, overall a pleasant surprise.
Third Best: Debian GNU/Linux, so many possabilities, if you only have the time to configure everything the way you want it.