If you want to play songs purchased from iTunes on your PSP, you need to burn them to a CD first. Apple allows you to make an audio CD in iTunes by burning tracks from your iTunes library to disk. These can be several songs from the same artist or a playlist of your favorite tracks from many artists. The following steps illustrate how to burn, rip and encode via CD burning.

1. Create a new playlist in iTunes.
2. Add songs to your playlist until you have approximately 72-minutes of music, which is the maximum supported by Audio CDs.
3. Verify your CD burning preferences in iTunes by opening Edit > Preferences > Advanced and checking the button next to Audio CD on the Burning tab.
4. After verifying preferences, click the Burn Disk button.

There's no direct way to copy files from an iPod to a Zune. Files purchased from iTunes music store will not play on a Zune, just as files purchased from Zune Marketplace won't play on an iPod. Using NoteBurner Audio Converter, you can get any MP3 files stored on an iPod onto a Zune.

MAC M4P Converter installs a virtual CD-RW, it helps you burn any unprotected or DRM protected M4P, M4a, AAC music files onto the virtual CD, rips tracks on the virtual CD, encodes tracks onto MP3, AAC music files. It can repeat this audio converting procedure until your whole music collection is done.

Since the virtual CD emulates your computer RAM and hard disk as erasable CD-RW drive (Virtual CD-RW), the converting speed is faster than any other m4p to mp3 conversion programs.

Now that the Sony PSP has a Web browser along with its existing wireless capabilities, this makes it possible to listen to iTunes music library on PSP, even though the library's actually on Macintosh.

What you need to do is to make sure that your Sony Playstation Portable (PSP) has been updated to the 2.0 firmware release and also make sure that you have a Mac running Mac OS X 10.3 or newer, and you need to download a copy of the application named Dot Tunes.