Problems with mp3 pen-drives to listen in the car

Hi everyone,
i'm from Italy and a new happy iMac 27" owner by 1 month..
i 'm really glad to have and use this wonderful machine , I come from years and years of Pc-Win.
The only thing, for now, that causes some problems is about  saving and listening, in my car, mp3 files on USB pen drives.
Before, using a a normal Pc-Win, i could save mp3 files and listen them in my car, but now using my iMac i can still save them but i can't listen them in my car. Something doesn't work.
if i create a pen-drive with my mp3 files i can listen only few of them, but many files don't play.
- I created the pen-drive (FAT formatted/initialized) using iTunes, drag and drop the files on the pen drive icon
- I tried to create the pen drive using only Finder App
- i tried to change the pen drive
- I tried to check the differences between the files that work and the others, but it seems there is no much differences
- I tried to erase the pen drive trash
.. nothing
the problem is still here, i can only listen a few tracks.
Somebody knows something about this problem ?
Thanks a lot in advance... sorry for my english

I bought an inexpensive set ($7) of portable speakers that run on 3 AAA batteries. My iPod plugs into it thru the headphone jack and has a little rest for the iPod. The sound results are pretty good and they are small so I can put it on the floor, seat or even in the cupholder and still hear my music. It kind of looks like the bookshelf sound system they sell only much smaller as the speakers are on each side of the ipod. I got mine at Big Lots. But I am sure lots of other places sell them.

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