|This article relies too much on references to primary sources. (October 2012)|
|Developer(s)||Ventis Media Inc.|
|Stable release||188.8.131.529 (October 22, 2014[±])|
|Preview release||None [±]|
|Written in||Mostly Delphi and C|
|Operating system||Microsoft Windows|
MediaMonkey (sometimes noted as M.M.) is a digital media player and media library application developed by Ventis Media Inc., for organizing and playing audio on Microsoft Windows operating systems. By using plugins, it can be extended to handle video and other media formats as well.
MediaMonkey uses the freemium licensing model; the base program is available as freeware but a premium gold license unlocks additional features such as the ability to have multiple media collections, the ability to organize files automatically, and others. Both editions can be extensively enhanced with skins, third-party plugins, and user-generated extension scripts. It uses SQLite to manage its database.
Music can be ripped from Audio CDs and encoded into most supported formats. Music can be burned to CD/DVD format in compressed or CD audio format, optionally normalizing the volume level of the songs in the process.
MediaMonkey's music library attempts to organize and categorize a user's music collection. Upon installation it will scan the user's hard drives for music files and add them to its library. Ratings and playback information can be imported from other media players such as Winamp and Windows Media Player. Podcasts are supported through the Podcatcher which allows the user to subscribe to podcasts that MediaMonkey will automatically download. It can also monitor the user's hard drive to ensure that any changes are automatically updated in the library.
MediaMonkey has support for third-party plugins to extend the base functionality. Available plugins include a Last.fm scrobbler, a plugin to show lyrics, and a web remote-control interface. MediaMonkey also supports the Winamp 2 API, allowing a user to use any of the many input, output, DSP, and visualization plugins developed for Winamp.
MediaMonkey was first developed in 2001 under the name Songs-DB. Songs-DB version 1.0.0 was released on October 12, 2001. Development progressed steadily with version 1.1 released June 7, 2002. Songs-DB 1.1 was the first version to provide Winamp plugin support. Version 1.2 was released on July 3, 2002 and included improved Winamp plugin support, significant UI improvements, and scripting support. Version 1.3 was released on October 31, 2002 and added Ogg Vorbis support and the ability to burn CDs.
For version 2.0, Songs-DB was renamed to MediaMonkey. MediaMonkey 2.0 was released on August 25, 2003. MediaMonkey 2.2, released on June 9, 2004, added iTunes-like device synchronization. This synchronization functionality was extended to include syncing to actual iPods in version 2.4, released June 5, 2005. The last major release of the 2.x series was MediaMonkey 2.5, released on December 28, 2005. MediaMonkey 2.5 added improved synchronization for all current iPod, Creative Labs, and iRiver devices, along with full FLAC support. Minor releases of MediaMonkey continued for the next year, culminating in MediaMonkey 2.5.5 which was released on January 30, 2007.
MediaMonkey 3.0.1 was released on December 25, 2007. MediaMonkey 3 was designed specifically with large user libraries in mind. This was seen in version 3.0.3, released on June 19, 2008, which increased the supported library size to 100,000+ tracks (from a previously advertised 50,000 tracks).
Media Monkey 4.01 was released on December 16, 2011. This version introduced better synchronization with Android devices, library sharing over DLNA / UPnP, improved audio output via WASAPI, the ability to run from a USB stick, and secure CD ripping.  
MediaMonkey 4.1.6 is the current release and it can do synchronization with Android and iOS devices.