Microsoft Zune Line (2006-2012)

Microsoft Zune 30

Microsoft released the first entry into the Zune line, the Zune 30, on November 14, 2006. It sold for $249.99 retail at release. The Zune was meant to be a direct competitor to the Apple iPod, but turned out to be a spectacular failure, and is often considered one of the biggest technology failures of all time. Microsoft discontinued the Zune line in 2011, and ended Zune support in 2015. 

Fun Fact: On December 31, 2008, at midnight, all Zune 30 models froze. It turned out that this was due to 2008 being a leap year, and the third-party driver for the included microprocessor. Luckily, all Zune 30 models were back up and running 24 hours later. The incident is often called "Z2K" and "Zunepocalypse".