Microsoft Zune

Microsoft's 2006 iPod killer arrived five years after the iPod and offered one differentiating feature: "squirting" songs to nearby Zune owners via wireless. The songs expired after three plays. By the time Zune HD launched in 2009 with genuinely good hardware, the iPhone had already made dedicated MP3 players irrelevant. Microsoft sold roughly 2 million Zunes total. Apple sold 22 million iPods in Q4 2008 alone. The brown launch color — "Double Shot" — perfectly captured the product's vibe: muddy and forgettable.