PC World has an article detailing the 25 worst tech ideas and why they think they're so bad. I think it's funny that AOL is number 1! I've always said, friends don't let friends use AOL.
On their list, I've used #2 (RealPlayer), #4 (Microsoft Windows Millennium), #8 (Microsoft Internet Explorer 6 - which PC world describes as "the least secure software on the planet."), #13 (IBM PC jr.), and I'm still using #15 (Iomega Zip Drive)!