Images: The worst technologies in Q3 2006

We could easily add the "new" iPod to this list, thanks to the fact that it doesn't do much that previous iPods couldn't do (except hold more songs, take up less space, and play Texas Hold 'Em). Instead, we'll give a tip o' the c(r)ap to iTunes 7, which boasted features such as resource hogging, freezing, deleting song files, album art issues, CD-importing woes, iPod syncing foibles and innovative new features stolen directly from Windows Media Player 11. In Apple's defense, the company released an iTunes update a couple of weeks after iTunes 7 came out. Maybe it's best that the iPod hasn't seen many significant "upgrades" over the past few years.