iRip 2 is a media extractor for iPods and iOS Devices. You can extract playlists, movies, TV shows, podcasts, ringtones, audiobooks, iBooks, and photos. You can move these files to iTunes or directly to a folder. It is a free program, but has a song limit before you have to pay (or do an uninstall of the program before using again, with a tool like AppCleaner).

iRip 2
IRip 2 Logo.jpg
Logo for iRip 2
DeveloperThe Little App Factory

Compatibility

It still works up to macOS Mojave 10.14. It might not work on Catalina due to a possible lack of 32-bit support.

Bypass Free Version Limit

If you would like to bypass the app's song limit, you can do an uninstall of the program by using AppCleaner (https://freemacsoft.net/appcleaner/). It will remove any data of you using past 50 songs. Also, if you move more than 50 songs at once, iRip 2 will not stop you. So, you can move the entire library of one iPod then use AppCleaner and reopen the application.

 
Screenshot from iRip 2

Download

Current version of iRip: http://thelittleappfactory.com/irip/