If you download and set up the program iTunes Agent http://ita.sourceforge.net/ you'll be able to set sync your G1 with an iTunes playlist (you're actually syncing the MicroSD card with iTunes, but it works the same). After you install the program, connect the G1 and follow the instructions here: http://ita.sourceforge.net/docs.html#how_do_i_add_a_new_device The "Recognize by folder type" field is important. It's basically how the program distinguishes your G1 from any other device you connect to your computer - I added a Notepad file called ANDROID to the root of the MicroSD card, seems like it can be anything that simple. In the "Music Folder" field, I pointed it to the Music folder at the root of the MicroSD card on the G1. In the "Associate with playlist" I left it as "use device name." Now, when you go to iTunes, under "My Devices" there should be a playlist icon that says "G1". Add whatever files you want (make sure there isn't any DRM) and then right click on the iTunesAgent icon in your system tray and click "Synchronize devices." Enjoy!