At least Bob came with a handsome sticker in the retail package.  (Still have mine on a toolbox somewhere in the garage!) I can't even say that about MS Dogs or Wine.  (heh...) 

Thinking back... the 900mhz cordless Microsoft phone and the Digital Sound System (both of which ended their effective lifecycles at the release of XP...)  nice timing on both counts...

Assuming we can't count Me (because even that would be too much of a "tip of the hat" to its mere existence..), I'm going to have to also vote for Works.  Notably, the pre-"Word-lite" versions of Works... I loudly declare the Works collection as "Microsoft's Greatest Misses".  ^__^

And although, yes, Barney sucked... it remains a recordholder in my book for "Best MS Knowledge Base Titles Ever", at http://support.microsoft.com/kb/172653/en-us