Comparing the programs
Synchronisation: If you’ve got an iPod or other Apple portable device, then iTunes is by far the easiest option. Windows Media Player can synchronise to most external devices such as MP3 players, but the process isn’t quite as smooth or reliable.
Sound quality: People who have particularly high-quality speakers and know how to set them up properly may find they can get a better sound from iTunes. However, for the majority of casual users, it will be difficult to notice any real difference.
Playlists: Windows Media Player’s library system allows you to create automatic playlists for a variety of criteria (artist, genre, year of release) with just a couple of clicks. iTunes requires more attention, but gives you much more options to make very specific play lists. There’s also a new Genius feature in iTunes which creates playlists of songs that are musically similar to a particular song you choose.
Look: It’s a very subjective matter, but many would argue that the look of iTunes is more attractive and practical than Windows Media Player, for example in the way the control buttons are much more prominent. One notable difference is that the iTunes 'Cover Flow' allows you to 'flick through' your albums, while Windows Media Player only shows your album covers side by side.
Customisation: The look iTunes is, to a large degree, not customisable. Windows Media Player can be changed through downloadable skins so that there is more chance of making it look and feel the way that best suits you.
Video: While the latest edition of Windows Media Player is set-up to make music prominent, it’s still a video player as much as an audio player. iTunes can play video (including video podcasts), but it’s much less flexible.
Streaming: Most wireless streaming devices can automatically synchronise with Windows Media Player to make it relatively simple to play your content on a TV set. iTunes has a similar system with the Apple TV device, but does tie you to that hardware.
Buying content: iTunes has a direct link to the iTunes store, making it very easy to buy legal music and video. Windows Media Player has links to online stores, but it’s not as well integrated and the range of content appears smaller.
Overall: Which program is best really does depend on your circumstances. In many cases, it will be a simple case of iPod users preferring iTunes and other Windows users finding Windows Media Player more useful. However, some users will find they consider some features more important, which can affect their overall preference.