Bill Gates: top ten greatest hits (and misses) - the Microsoft years - Engadget
Hits
Internet Explorer (IE)
Introduced 1995 - followed netscape, without bundled with windows, it couldn't have lived.
Media Center
Introduced 2002 - this is useless to me, I never use it, before PC has a good OS for TV Screen, I dont think this thing flies.
MS-DOS
Introduced 1981, discontinued 2000 - bought from IBM.
Office
Introduced 1989 (on Mac), 1990 (on PC) - bought from many companies and there's less and less reason to upgrade.
Peripherals
Introduced 1982 - xbox360 driving wheel has driver issue, what's going on?
Windows 3.1 / NT 3.5
Introduced 1992 and 1994 - crash like hell but nothing else available any way. I used win3.2, win98se for long time.
Windows 2000 and XP
Introduced 2000 - XP was not so good at start but it's good now. I still like classic windows look, instead of xp look, dislike vista look.
Windows CE / Mobile
Introduced 1996 - followed palm, this becomes a slower and resource killing OS, even for now. most M$ application on CE wont quit, is it so hard to call Application.Exit()?
Xbox and Xbox 360
Introduced 2001 and 2005 - xbox360 RRoD and they dont want to promote HD-DVD to make it winner, now ps3 will catch soon.
Visual Basic
Introduced 1991, discontinued 1998 - screen shot is old basic, not visual one, never liked this, I miss PASCAL and Delphi.

Misses
Origami / UMPC
Introduced 2006
Note: Intel, please join Microsoft on stage to accept this award - it was promising, I dont need those stupid buttons or keyboard, but it's still too heavy and too expensive. mini-notebook like eeePC and msi wind will win, not UMPC.
Windows Vista
Introduced 2007 - explorer 100% CPU for certain binary files, very very very ... slow.