I got an iPod a while back because I got tired of using shitty ass mp3 players. I had a tiny MuVo that was okay, but it only had 128MB space and only a play and two tracking buttons. Great for jogging, but that's it. I then got a Lyra, which was decent, but it crapped out after a couple months with a bum hard drive. So, since I had the dough, I just decided after having the Yugo and a Chevette of mp3 players, I would go straight for the Cadillac.
So I have a black 30GB video iPod with a large chunk of my entire music collection on it set to shuffle, and I haven't heard the same song twice in months of driving. Plus, if I'm at the doctor's office or waiting similarly elsewhere, I can watch TV shows I ripped from DVD. Very nice. And I have it in a black rubber shell w/plastic screen that keeps it from losing that nice black finish and scratching the screen all to hell. Plus it keeps it disguised.
I usually leave it in my car while milling around in town, but I keep it in my glove box. And if anyone tried to mug me for it or anything else, I have a .357 solution for that problem.