Here is a cool program that helps you use sync itunes music, podcast, movies etc to any thumb drive, mobile or even and external memory card. If you have the Sony Walkman series phone the settings are already there. But if you have some other mp3 player or mobile that shows up as a hardrive on your system. You can sync it with itunes. Just go here and download iTunes Agent. Once installed when you open this program it will auto launch itunes. Add a new profile with the same settings as shown in the picture. And make a folder called "ITAGENERIC" on your player. Once you make the folder itunes agent automatically recognizes your player or thumb drive or memory card. Create a playlist on itunes and give the name "Generic Player" you can select any parameters for that and it will sync this playlist with your player. Now you left click the icon in the task bar and sync it. Remember its only one way, so you can replicate what's on your itunes. If you want to delete something just do it on the itunes and it will be reflected on player when it syncs next time. It quite a bit of work but once you set this up next time just connect the device and click sync and it sync, its that simple.