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Plan 9 is the worst expiriance, but Amiga is the most Ugly.
Plan 9:

You put Windows and "GNOME, etc." in the same category? Oh dear... That Plan 9 screenshot looks pretty cool, actually...

The worst GUI I've ever used that's in your list is Mac OS X. To be fair, I didn't know what I was doing, but even simple things (what made them put the menu up there?!? and if I want to maximize this thing, do I want red, yellow, or green? ) were rather tough for someone used to the Windows way of doing things. Plus, I couldn't figure out how to launch any kind of command prompt, which is a fatal flaw in my opinion.

http://toastytech.com/guis/bob.html

Strangest thing ever, it's a Windows 3.1 shell for computer newbies...

Quote:c:\>_

Or GEOS, MacOs7.X At Ease, Mac Classic, Windows Me, Windows 3.11.

I have to admit, XP isn't too bad to look at. But its already 5 years old, I don't like the look of Vista. I'd like to see screenshots from Windows Codename Vienna (ETA 2011) when they are released.

Although I would love to make my own OS. Perhaps something that brings out an entirely new concept, with the ability to have the original feel to it?

Definately GEOS...ugh. GEM on the Atari ST was pretty llama as well.

anarky, one of my current projects is an OS. It's fun stuff!

Ooh... MSN me!

The GUI for the Atari ST was pretty clunky. Motif, CDE, raw X and most of the other old Unix GUI's are fairly awful too.

I used to like GEM on the Atari ST, but now using it on an emulator it seems horrible.

Early XFree is definitely the worst. GEM and GEOS had an excuse, but XFree and applications were just plain bad for so long it's a bit sick.

Quote:anarky, one of my current projects is an OS. It's fun stuff!

You too? Is yours a stand-alone OS?