Freedom From iTunes
This program is probably the easiest to learn of any software in our list. Because Anapod Explorer integrates into Windows Explorer, managing your iPod is a simple matter of dragging and dropping. This lightweight program uses other Explorer controls as well, such as Send To menus and copy and paste. Among Anapod Explorer's dizzying array of cool features are automatic repairs to mislabeled or duplicate songs, playlist management, and support for transferring files from iPod to PC and vice versa. And unlike iTunes, Anapod Explorer invites you to use templates to customize the way your iPod displays tracks. Anapod supports MP3, WAV, WMA, iTunes Music Store music, and more. And though it lacks a built-in media player, the Anapod Xtreamer lets you play songs through your favorite media player via HTTP streaming.
This great program comes at a cost, however. Depending on what model of iPod you have, prices range from $20 to $30. Though there is a free trial edition, its features are very limited. And like other software listed here, Anapod Explorer currently doesn't support the iPod Touch or the iPhone.
Download Anapod Explorer | Price: $20 to $30, depending on the associated iPod model
Like Anapod Explorer, XPlay 3 integrates into Windows Explorer and works with Windows Media Player and Media Center (or with iTunes, if you prefer). It uses the same file-management controls that Windows Explorer does: You can drag and drop files, use the Send To menu, and so on.
XPlay 3 doesn't have as many features as Anapod Explorer--for instance it lacks custom skins and tagging templates--but it does offer quick tagging, album art editing, and playlist management options. You can use XPlay 3 to manage photos on your iPod, too. It costs about the same amount as Anapod Explorer ($30), but the trial version of XPlay 3 is fully functional, so you can give it an accurate test run before buying it. Once again, the software is not compatible with the iPod Touch or the iPhone.
Download XPlay 3 | Price: $30; free trial available
Like Songbird, Foobar2000 permits third-party sources to create add-ons that extend its functionality. If you are looking for a media player that's heavy on aesthetics and visualization, you might want to look elsewhere. Foobar2000 has a minimalist interface, which you can customize according to how you want to organize and view your media library. Foobar2000 can play a number of formats (including Ogg Vorbis and FLAC) that iTunes does not support. The player delivers high-quality sound output with support for ReplayGain, an algorithm that maintains consistent playback volume for audio files. In addition, you can rip CDs and convert audio files to another format, such as a playlist, using the Converter component.
As the Foobar2000 site observes, this is an "advanced" audio player, meaning that it isn't as user-friendly as iTunes. In audio quality, however, it is superior. Download the player and learn its basic functions before you begin downloading the optional components (which, among other things, allow you to play copy-protected music files from iTunes). Regrettably, this app isn't a wholesale replacement for iTunes: You can't sync your Foobar2000 library back to your iPod.
Download Foobar2000 | Free