Which GUI is the closest to Windows? I am a long time windows user and want to break my self in slowly with Linux. I hate Microsoft with a passion, and want to get away with it completley. How can I ease my MS pains?

try KDE

there is none that i can think of off hand, but i am willing to bet there is something that is a spit image of the ms gui, but what are you using now? i mean personally i would have to say KDE and gnome, work in a sense the same way as the windows gui...it has the start button equivalent, and shortcuts on the desktop, and a control panel equivalent....so i am not sure what else you could be looking for, cause i am going to have to assume you use one of the two environments...
i guess if you wanna go on a limb and try Lindows, you'll probably get what your asking for...i personally wouldn't go near it with a ten foot pole, but it may be something your interested in...
but of course you must realize that it involves reloading a new system, and not simply change your graphical environment...

xpde is specifically designed to look'n'feel as much like Windows as possible. IceWM can be configured to mimic Win9x to an extent, more in superficial look than feel. But, really, nothing makes me feel like I'm using Windows more than using KDE or Gnome. *shudder*

Just stay away from fluxbox or Enlightenment or WindowMaker or fvwm or whatnot if you want a gradual transition.

I was exclusively fluxbox until I gave Ice another try and decided a fully functional taskbar was nice to have once in awhile.

thanks for all the replies so quick.. I will try xpde first and go from there, I guess the 2nd half of the question is how hard is it two switch GUI's?

Depends on what distro you're running and what runlevel. It can be as easy as changing 'exec foo' in ~/.xinitrc to 'exec bar' but can be more complicated. If you gave that information people could help you better.

What do you mean by distro? like version? I'm running KDE right now, and it's Red Hat 9. I'm still updating it right now as I type this.. and I'm a ultra newbie to linux, yet I'm a fast learner when it comes to computers..

Sorry - distro=distribution=(in your case) Red Hat 9. Runlevel is a somewhat complicated issue - the shorthand in this case is do you log on at a command prompt or a graphical box. And somebody else will have to help as I've never used RH and RH defaults to a graphical logon, I believe, which means you have to mess with display/session managers. Don't worry about being new to it all - and being a fast learner is great. Sure wish I was. I'm slooow.

you can use a windows manager, XDM, KDM, GDM, to switch between environments, so if you have the space you can install 3 or 4 or more enviroments, KDE, GNOME, ICE, Xfrce, xpde. with a windows manager you can chose the environment you want when you log in.

Could I suggest a different strategy? Install fvwm2 and teach youself to configure it - using ?.fvwm2rc. This is not as difficult as it seems at first and, when you have your perfectly customised desktop, then, because you've made it yourself, you'll be very good at using it.