How many times do I have to repeat myself? You need a wireless PC adapter. The device you are connecting is the Play and Charge kit

http://www.xbox.com/en-US/xbox360/accessories/batterieschargers/xbox360playchargekit

and the device you need is

http://support.xbox.com/en-US/xbox-on-other-devices/connections/xbox-360-wireless-gaming-receiver-windows

Jacadcaps,

I'm terribly sorry I missed your coment on the wireless PC adapter.

Are you getting my point? (Hint: At times your posting style comes across as stupidly arrogant).

I have a Xbox 360 wired controller, and from what I understand in this thread it doesn't load automatically. Well, this is true for me as well. I have to start System Prefs --> USB to get it to work. But by just doing this, the controller comes to life.

Should I expect it to act like this in the future as well?

Saving USB settings will make it stick.