I maintain to this day that the Zune was one of the best designed hardware and software platforms I've ever used. Probably the only truly design forward product that MS ever produced.
Their only misstep was making one of their colorways poop brown! That and being too late to market with a phone that used the same design language
There was also the crap that was Windows Media Player 11 which I tried to like for about a month.
There was also the incompatibility with Microsoft’s own DRM ecosystem in PlaysForSure which was full of these subscription music services, some of which were quite popular with the kind of people that were inclined to buy a Zune: folks in Microsoft’s ecosystem that had passed up on using an iPod and used something from SanDisk, Creative, Toshiba or iRiver instead. This is because they wanted to replicate the entire iPod+iTunes model entirely.
The 2006 lineup of iPods was also particularly strong, and included the first aluminum iPod nano’s. When Microsoft announced and released the Zune, they were counter-programming against that, right into the Holiday season with a new brand that had no name ID, with a product that was just like the iPod, couldn’t play any of your music from iTunes or Rhapsody, but with… HD radio.
More than a few missteps were made.
> Their only misstep was making one of their colorways poop brown
I mean, iPhone is a really ridiculous name as well if you stop to think about it.