If the jack were at the top, why wouldn't you just put in your pocket rightside up? When we travel, we use our iPod classic, set in a cupholder of the car's center console. Jack at the bottom isn't ideal. Plugged into my stereo, it's just less of a hassle to have it come out the top when picking music. When we use the iPod Tough with the jack at the bottom, it always seems to be in a clumsy location for cord management. I haven't figured out the advantage of having it at the bottom, but then my wife always says I'm "different". ;-).