Launch date: May 6, 2010

Fatal flaw(s): Underpowered, misguided marketing, lack of features

Here we are: Number one. The Microsoft KIN. Really? Really. Here's why. KIN, a smartphone platform developed by Microsoft and aimed at younger users who were heavy social network users, wasn't horrible. The KIN One, though very slow, was charming with its pebble shape and solid sliding screen. The software, while lacking needed features like a Maps app, was attractive, inventive at times (the Spot and Loop were cool), and relatively easy to use—although it felt cluttered enough to give claustrophobes the creeps. So why did Microsoft pull the plug after only 48 days? 

The problem laid not so much in the phone itself as in Microsoft's approach to getting the phone into people's hands. Sure, the phone wasn't great—definitely not a threat to the iPhone, BlackBerry, or any Android phone—but a lot of phones aren't great and they're still getting churned out. We think Microsoft flubbed by trying to dictate who was supposed to buy the KIN. It seemed as if the phone's drawbacks were explained away by saying that its target demo didn't need those missing features. If any Microsoft exec took a ride on the MTA Subway they'd see teenagers using the same BlackBerry as Wall Street bankers. Younger people, like their future selves, want cool phones. Not kid phones. 

There are worse products on this list, sure, but in terms of failures, we don't think anything matches the $1 billion development and marketing expenditure and the month-long shelf life of the KIN.