iTunes vs Zune vs Songbird: Music Organizer Showdown
Music, music everywhere, and a ton of programs with which to organize it. But how will you know which of the many iTunes-equivalents (if not iTunes itself) are going to be right for your needs?
If you're one of the many people using Windows' default music libraries to organize and store your files, stop. Just stop. There's so much more you can do beyond that-which-is-given by Windows Media Player's library features, it's not even funny. Conversely, if you're one of the people who clings to Apple's iTunes with a death grip by virtue of it being one of the first big music organizing tools to really "stick" amongst the general geek population... you might be in good hands. You also might be missing out on a ton of additional functionality, depending on what you're looking for and how you typically go about rocking out on your computer.

To keep the playing field fair, we'll look at three different applications in this ultimate guide to media organizing: iTunes, Songbird, and Zune. For those keeping score at home, that's one big solution from Apple, one big solution from Microsoft, and one big solution from the open-source community. There are certainly other options around--Foobar comes to mind as one such example. None are as comprehensive in their combination of features and/or customizability as these three, however. They're all easy to install and easy to set up, but which application has the features and usability that'll make it a hit?
iTunes
Apple introduced iTunes into the world at the 2001 Macworld Expo. At the time, it was fairly trimmed-down piece of software that was really only meant to do two things: play audio files and burn discs in a single program. Apple's app wasn't quite as slick as its chief rival, Windows Media Player 7. The latter built Internet connectivity into the usual list of media playback features to deliver a player that could not only burn and rip CDs, but also connect to Internet radio, surf online media guides, and download new skins for the whole application.
My, how times have changed.
Awesome
Apple Support: Duh. Apple's iTunes is the only media player/organizer that fully supports all the features of Apple's various handheld products. Other media organizers simply can't bypass the encryption Apple keeps between its products and its players.
Online Store: It's hard to deny the power of Apple's online store. With downloads of more than 8.5 billion songs, three billion apps, and one million video files since its inception, the iTunes Store is a veritable powerhouse of content in the marketplace.
Customized Data Dump: Want to list your music by the last time you accessed the file? Okay. You're your music by beats-per-minute? Sure! Want to organize your files by bit rate? Go ahead. iTunes comes with a full list of sortable options for listing your jams.
Powerful Playlisting: Automatically assign new songs to a playlist based on customized criteria you select. It's a perfect way to have a perfect, hands-free organization for your music library.
Unfortunate
Apple Authorization: Want to connect your app to your iTunes Store account? You only get five authorizations (and one do-over) per year. That's not much for a single computer user, but if you're running iTunes on multiple devices using one account, and forget to deauthorize your computers when reinstalling the OS, you're hosed.
Clunky Interface: Beauty is in the eye of the beholder, but I can't help but feel that the iTunes UI is a bit kludgy. Throw in Apple's marketing efforts--like the Genius-based callbacks to the iTunes Store, as well as the entirety of the iTunes store itself--and the whole app just feels a bit out of its element on the Windows platform.
Lookups, Schmookups: Apple's iTunes isn't that good about looking up cover art for MP3s you've imported, even when the album seems pretty easy to identify-in my case, the Avenue Q soundtrack. If the ID3 tags aren't perfect, isn't there some kind of fancy technology iTunes can use to suggest a best-guess fix?
Lost Music? Lost Money: Delete a track you've downloaded from iTunes and you're stuck--unless you send a mea culpa to Apple itself, you'll have to repurchase the song from the iTunes Store.