Do you have a memory card if so plug your bb up to your computer go to my computer then select memory card or mass storage device and it will have a music folder in it open it and then drag and drop your music works perfect on my phone
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i use this prog, it makes it easy to transfer your itunes playlists you just click on the playlists and hit sync.....except if you purchased it from itunes and its protected....wont let you transfer those songs
I'm with nastyneon on this one. I prefer the drag and drop approach rather than using Roxio with Desktop Manager.
Follow the instructions nastyneon gave you. Once the BB is hooked up it should should up as a removable storage device under "my computer" on your pc. Simply grab the file you wish to transfer and drop it into the removable drive.