Worst:
1. Any AmigaOS with WarpOS installed.
2. Windows ME (does anyone out there like this OS?)
3. Windows XP with all of the eyecandy turned on
Best:
1. FreeBSD/Gentoo Linux with Gnome 2.2.
2. C64 Basic (C'mon, it was an OS that *never* got in your way)
3. Windows 2000.
Now if this question was asked ten years ago, it would've been AmigaOS all of the way .. but in the past ten years there has been no *major* OS development, and the minor updates that there has been has been simply to copy MacOS and Windows..