iTunes is Apple's software jukebox. It started out as a Mac-only app before making its way to Windows users in late 2003. The software will let you manage photos, videos, and music files on your computer, then sync them up with Apple's array of portable media players.
People have mixed opinions of iTunes since it's only been open to Apple branded devices like the iPod and iPhone instead of being open to many competing devices as a platform. Despite this, it was one of the first mainstream programs to offer Internet radio and CD-ripping free of charge in a time while other jukebox software providers were not.
One of the reasons it's free is the inclusion of the iTunes Store, which lets users buy music, TV shows, audio books and movies, as well as subscribe and browse podcasts. This year, Apple unveiled the iTunes rental store, which forgoes the usual $10 purchase fees for films and lets users rent them for a limited period of time for about a third of the cost.
Winner: iTunes (Apple.com/iTunes)