OS/2
Can you imagine if IBM didn't abandon the development of OS/2? One of the biggest mistakes IBM ever made. I used OS/2 in a professional and personal environment beginning in 1988 all the way through Merlin, or Warp, in 1994. As a matter of fact, Windows was more stable running under OS/2 than standalone.
I needed the ability to make at least 8 simultaneous remote connections...on demand and on autopilot. DOS and Windows...no way. UNIX and OS/2...no problem. Obviously, I would've chosen UNIX, but I was employed in a 100% IBM shop and the powers that be thought UNIX was just another four letter word.
I know I often slam Windows, but someone has to stir the pot. Fact of the matter is; I like all operating systems. The newer versions of Windows make great clients, but I would crawl miles over broken glass before I'd ever use if for anything mission critical. I'm not a fan of check box operating systems.
Comparing Windows to OS/2 is like comparing DOS to UNIX.
A brief history of OS/2 can be found here, and the Wiki is here.