Oakleaf, good info!

I have a 1/8" male-male audio cable for my car so I will see if he has an input for that on his stereo. I'll try it out with my iPhone. His car is just a few years old. I'll have to check it for an audio input. That would be a very simple solution. I'd hate to get him a present that would force him to upgrade his stereo in order to use it! Isn't there some kind of wireless gadget that you can use with the car stereo where you tune the car stereo to a certain frequency and it picks it up?

We're Mac people here too. It would be synced to an iTunes library on my Power Mac. I wouldn't know how to use anything else!

So is the Nano good for all of this? Or should I get one of the classics?