Having an iPod, iPhone, or iPad doesn't mean that you have to use iTunes to purchase your digital music. Similarly, if you already have an existing media library that you want to sync with an Apple device, then you aren't restricted just to iTunes. In fact, there's a good deal of free iPod-friendly software on the Internet for managing and syncing media files to your portable. If you're having problems with iTunes, or just fancy a change, then this list of iTunes alternatives will show you some of the best free media software that is compatible with Apple's range of portables.
Winamp which was first released in 1997 is a full-featured media player. Since version 5.2, it has supported synchronizing DRM-free media to the iPod which makes it an excellent alternative to iTunes. There's also a version of Winamp for Android-based smartphones if you want an easy way to move your iTunes library over. The Full version of Winamp is free to use and sports a whole host of features that will satisfy most people's needs. However, if you want it all, then you can go pro for a reasonable upgrade fee.
Media Monkey is a free music manager that can be used to manage large digital music collections and is compatible with the iPod -- not to mention other MP3 players and PMPs too. The free version of Media Monkey (Standard) comes with a plethora of useful tools for organizing your music library. You can use it to automatically tag music files, add album art, CD ripping, CD burning, and converting audio files to iPod-compatible formats.
Foobar2000 is a light-weight but powerful audio player for the Windows platform. It supports a wide variety of audio formats and can be used to sync music to an iPod. With the aid of optional add-on components, Foobar2000's features can be extended -- the iPod Manager add-on for example adds the ability to transcode audio formats that aren't supported by the iPod.
Amarok is a multi-platform media player for Windows, Linux, Unix, and MacOS X operating systems that is a great iTunes alternative for your iPod. As well as using it to sync your existing music library to your Apple device, you can also use Amarok to discover new music by using its integrated web services -- Last.fm, Magnatune, Jamendo and others can be accessed straight from Amarok's intuitive interface. Other integrated web services like Libravox, and OPML Podcast Directory extend the functionality of Amarok to make it a powerful software program. With the inclusion of MP3Tunes as well, you can create your own music locker to create a cloud storage option for your media library.
MusicBee which is available for Windows has an impressive amount of tools for manipulating your music library. If you're looking for an iTunes replacement that's got an easy-to-use interface, and packs more features than Apple's software, then MusicBee is worth a close look. High on the list of features includes: extensive metadata tagging, built-in Internet browser; convert audio formats and sync on-the-fly, secure CD ripping, and more. MusicBee also has features useful for the Web. For example, the built-in player supports 'scrobbling' to Last.fm and you can use the Auto-DJ function to discover and create playlists based on your listening preferences. Overall, a great iPod-friendly music manager that also has tools for the Web.