Winamp on windows or whatever comes with the linux distribution. Winamp is the only media player I've tried that will automatically sync to a usb device without trouble. Last I used songbird it just dumped all the files unceremoniously onto the root folder whilst deleting all the ringtones. I filed bugs and the ringtone deletion was marked wontfix, and the folder setting bug was marked solved because you could manually edit some obtuse xml file to make it use another folder. I'm not going to bother with that software again.