Originally Posted by zGuy
You can set your BB's MSMS (Mass Storage Mode Support) to "On"/"Yes" Options >>> Memory >>> MSMS "On" and "Yes" when connected. Then Save!
Now, when connecting to your Mac via USB, your BB will show up as an icon on your Desktop. Double-click on it and go to the Music portion of the files. Now just drag songs from your iTunes directly into your BB.
Side note: Your OS must be Mac OS X version 10.5.5 or higher! I bet most people don't own Macs this new.
I do see the BB as an attached drive (and I'm running only 10.4.1 by the way) and I suppose I can drag and drop but doesn't that lose a lot of the iTunes database info? Can I drag a playlist? Thanks