Launch date: 2004

Fatal flaw(s): No MP3, WAV, or WMA support, expensive 

To be fair, the HD1 had a lot going for it when it was released. That's part of the reason why it was such a fail of a product. The sleek, aluminum body was a pleasure to hold, and it was one of the smallest, if not the smallest 20GB music player available at the time. However, it's weak spot came in the form of Sony's ATRAC3 format. In order to play any music you had to convert your MP3s into its proprietary format using its shitty SonicStage Jukebox software. Then there was the price. Oh, and this little thing called the iPod.