Blackberry Pearl Music 
Got myself this app called PearlSync (US$10), which reads playlists from your iTunes and synchronizes them to your Pearl. While useful, it is very slow: an hour of running and I have about 25% of my playlist sync'd up. Clearly this is best run overnight.
That said, the media player on the phone is very nice, providing better quality sound than I'd thought it would. (Definitely better sound quality than the laptop provides today.)
One note though, there is no adaptor for the Blackberry to permit you to use standard headsets with them.
Another interesting thing to note is that you can get car stereo head units which understand bluetooth. This means you can stream MP3s to the car stereo and use it as a hands-free phone set. Some head units require a bluetooth kit to make this work, but BestBuy has a Sony one which has a mic built into the head unit itself for about CDN$200. It is probably a cheap mic, but it will let us get the job done.