Rio Karma MP3 player (2004).
This was before touch screens, when we had to rely on hard keys provided somewhere around the screen. The huge majority of hand held devices come with the controls at the bottom, below the display.
The Karma did the opposite, and that was daring. It was surprisingly comfortable, as the thumb would effortlessly meet the wheel and buttons located at the top, making the player very natural to use. But not everyone liked how it looked.
An example of product that didn't sell as much as it deserved, just because we're usually not ready to buy things that look too unusual, even if they're a delight to use. To be fair, the Karma was probably not ideal for lefthanders!