Launch date: November 14, 2006

Fatal flaw(s): Too little improvement too late 

When Microsoft released the Zune music player, CEO Steve Ballmer said that he thought his company could overtake the Apple iPod in the portable music player market. Nearly five years later, Apple's iPod claimed 77% of the portable digital music player industry, and Microsoft let it be known that the Zune was being discontinued. Well, sort of. According to reps at the company the newly introduced Windows Phone 7 handsets will be the "new Zunes". 

Granted, the first three generations of Zune weren't up to snuff, but the last one, the Zune HD, was a marvel. It was thin, sleek, made from quality materials, and had an inventive interface, different and in some ways better than the iPods. It's a shame it took Microsoft so long to get it right.