I guess we could put a red X through the now and put the newest one on the side of his thigh. Actually it'll probably just serve as a reminder of a particular time in his life.One of his friends asked him why he was even getting something video game related and he said that gaming was a part of his life so why not.
I was actually talking to him about addin' characters from each system around the controllers. Like Mario, Link and Donkey Kong around the Nintendo one and characters from GTA, COD, Halo and Mass Effect around the 360.
Issues of the tat becoming outdated aside, the 360 controller really is the best controller around right now. The only issue I have is the d-pad and it's not that bad. But, it's the most comfortable one to hold and so easy to use.
Adding characters around the controllers is actually a cool idea too. you should make sure the ones surrounding the NES pad are all 8-bit though. That would really sell the whole then/now concept too.