MediaMonkey is a music manager and jukebox for serious music collectors and iPod users. It catalogs your CDs, OGG, WMA, MPC, FLAC, APE, WAV and MP3 audio files. It offers an intelligent tag editor which looks up missing Album Art and track information via Freedb and the web, and an automated file and directory renamer to organize your music library.

  • 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
  • Create playlists and music mixes quickly and easily to suit any occasion
  • Synchronize with iPods / MP3 players effortlessly and convert tracks on-the-fly
  • Download audio content using the new integrated Podcatcher.
  • Use MediaMonkey for Parties or other public places with Party Mode
  • Create Statistics and other Reports of your music collection as Excel, html, or xml files.
  • Customize MediaMonkey with Skins, visualizations, plug-ins and scripts to make it do what you want it to.
  • Plus much more...

Website: Ventis Media - 7.22MB (Freeware)
View: Addons
Download: MediaMonkey

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I like Media Monkey, and have to admit it isn't at all bad. Know having said that, here is the down fall of Media Monkey—they want to charge you for things that are free in iTunes, and WMP, hence, not worth having.

It is a minor update to that includes a fix to auto-tagging from Amazon which recently broke due to a change in signature handling.

Danger! If you have an established library of music, on your desktop or iPod, this software can seriously render it a pile of digital goo. Be very very careful!