Mac Copy Utilities
You can use third-party utilities to copy information to and from your Mac to and from your iPod. When using Mac copy utilities, remember that copying copyrighted material without permission is illegal.
iPDA: With this software, you can transfer personal information to your iPod from Entourage, Mail, Address Book, and iCal. You can even download weather forecasts and news headlines directly to your iPod.
iPod Access: This comprehensive utility lets you transfer songs from an iPod to a Mac (Windows version also available) with song information and iTunes ratings. Loaded with features, iPod Access supports On-The-Go playlists and playing music and video directly from an iPod. It’s available for $19.99 from Findley Designs, Inc.
Senuti: This program lets you copy songs to your computer from your iPod. You can search for songs and even play songs directly from your iPod with the program. Senuti reads the playlists on your iPod and lets you to transfer them to your computer. You can also automatically add songs to your iTunes library.
iPodRip: This third-party utility, available from The Little App Factory for $14.95, lets you transfer music from your iPod to your iTunes library and listen to music on your iPod through your computer (saving hard drive space). It supports all iPod song formats, including MP3, AAC, Protected AAC, and Audible.com books.
YamiPod: Yet Another Manager for iPod (YAMiPod, get it?) is a freeware application that lets you copy music files from your iPod to your computer and vice versa. It can copy playlists, really simple syndication (RSS) news feeds, and podcasts and synchronize your iPod with computers running Mac OS X, Windows, or Linux. You can run it directly from your iPod.