If you buy the songs from the iTunes store and they are DRM'd (as most of teh 99 cent songs are I believe) you can not play them on the 8300.
If you burn the songs yourself from a CD, into AAC (non-DRM'd) or MP3, they should work I believe.
If you download a Podcast, which is usually MP3, it should work.
I use Missing Sync for BB, which includes a handy sync for iTunes making this process much easier....
|