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I just thought I'd mention RealPlayer as it has a history of being adware and spyware-ridden. And the last time I dealt with RealPlayer, I remember finding parts of the program which hadn't been removed after uninstalling.

I also have to mention Windows Millenium Edition. Most seasoned Windows users have heard or experienced the problems surrounding WinME... slow startup/shutdown and other related problems, poor driver support, frequent freezing and crashing and an abysmal management of memory and little difference (to the end user) when compared to the more stable Windows 98.