I've always been a stickler for my media library (mp3, photos, video), and I've finally grown comfortable with the system I've put together for my music collection.

MediaMonkey has been one of my favorite software purchases of my life. It is a solid platform which can handle everything that I've found other software to be woefully inadequate in. When I first tested iTunes, it would crap out very quickly and was obviously programmed with Apple's mantra ("Apple knows best"). Windows Media Player wasn't as bad, but is painfully slow with a large library. Both iTunes and WMP suck at carving out your own library. MediaMonkey, on the other hand, is an organizational dream. With the help of some free user-written plugins, my music is automatically tagged with applicable genres, instruments, country of origin, original release year, insturmental/vocal, male/female vocalists, mood, occasion, etc. all based on a white-list of terms that I created. This makes finding music very easy since I can be terrible with remembering artists/albums/track titles when it comes to something obscure.

Not only that, but it also is my DJ. All I have to do is pick a seed song and it will come up with songs that are similar to that song. Pair this with the ability to automatically rate the tracks I listen to completely higher than the tracks that I skip and the more I listen, the more accurate my auto-DJ becomes to my own personal taste. This includes songs that I play on my Android phone. My phone is synced using MediaMonkey as well based on some rules that I set up. For example, I have it sync music that I've rated high (4-5 stars only) and only music that I haven't heard much recently.

All of this combined with a number of other features not mentioned make MediaMonkey one of the best tools for an audiophile like myself.