Webware 100 winner: iTunes

Site: Apple.com/iTunes
Category: Audio & Music

iTunes is Apple's jukebox software and a gateway to Apple's online media store and portable devices like iPods and iPhones. It's currently in its eighth release, and now features a built-in recommendation tool that can create playlists based on listening habits from your library, as well as other iTunes users.

The software started out as Mac-only, but became cross-platform with Windows shortly after Apple realized that it could make more money from music and movie sales than with iPods alone.