I love these lists - and this one made me laugh. Being a company man, I cannot agree more with #1 and #2 on this list. Also, being a fair-minded individual, I also agree with #4 - it deserves to be on this list, but I don't know that I would have put it quite so high.
But Microsoft Bob? Unnecessary and useless, yeah, but WORST? I don't know about that. I will always have a soft spot in my heart for Bob...
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Correction: Originally I typed, "being a fair-minded individual, I also agree with #3..." I did not have anything to do with SoftRam - this was a typo. I have fixed the quote to read "#4" - Windows Me. I was on the Internet Explorer test team for Windows Me - you can partially blame me for that fiasco, I guess.