For many of us, listening to music — and managing our collections of music — can be as important as making music. Jaymis has me sold on MediaMonkey, available in cheap / free versions, for Windows. Note that this doesn’t run on the Mac — feel free to discuss Mac alternatives in comments. Listening software is often one of those few apps we run every day, so here’s Jaymis’ exhaustive review of his favorite. -PK

I received my first MP3 file over ten years ago, as a zip archive spanned over three 3.5″ floppy disks. In the time since there have been advances in codec, hardware and software players, metadata formats and online sales, but after more than a decade the humble MP3 is still a dominant force in computer based music listening.

In my time as an MP3 consumer I’ve used a plethora of players, both hard- and software. In the early days, developers racing to add new features had me switching and trying out new applications regularly, but by the late 90s I was a dedicated Winamp user, even through the troublesome Winamp3 days. This all had to change. When faced with a year travelling and working in Europe I decided to retire my trusty 256MB “James” and replace him with a shiny, white, inevitable, 20GB (3rd Gen) iPod. After considerable wrangling (warning NSFW language and unrelated ranting in comments) I grudgingly switched to iTunes, which is an ok piece of software. Really. If all of your music comes to you via iTunes music store or major label CDs you’ve faithfully purchased and ripped (after reading and understanding any included EULAs) then you probably won’t ever need or want another media player. iTunes also has some truly fantastic features: Coupled with judicious iPod-based rating while travelling, Party Shuffle and Smart Playlists changed how I listen to music.

However, If you’re a discerning music listener. If you consume music which is copied from friends or MP3 Blogs, acquaintances with bands, records digitized from your dad’s vinyl collection, or if you occasionally change computers, use multiple computers or multiple ipods, then iTunes will eventually cause you grief.

It’s not the most full-featured application either. Apple’s “less is more” philosophy does make for friendly, simple software, but a quick look at Apple’s supplied Applescripts give you an idea of the basic functions they haven’t bothered with.

Enter Mediamonkey

MediaMonkey is amazing. I’ve been running it for 3 months now and still feel like I haven’t scratched the surface of what it can do. Here’s a quick feature overview from the site:

• Organize music and edit tags in your audio library with a powerful, intuitive interface
• Automatically lookup and tag Album Art and other metadata
• Manage 50,000+ files in your music collection without bogging down
• Play MP3s and other audio formats, and never again worry about varying volume
• Record CDs into OGG, MP3, FLAC and WMA files
• Convert MP3s, OGG, FLAC and WMA files into other formats with the Audio Converter
• Synchronize with iPods / MP3 players effortlessly and convert tracks on-the-fly
• Party Mode, which allows users to make requests while protecting your library from being modified.