MediaMonkey for Windows (sometimes referred to as MMW) 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 expanded to manage video formats and other media. MediaMonkey uses the freemium license model; the basic program is available as freeware, but a Gold Premium license unlocks additional features such as the ability to have multiple media collections, the ability to automatically organize files, and others. Both editions can be significantly enriched with skins, third-party plugins, and user-generated extension scripts. It uses SQLite to manage its database.

Music can be extracted from audio CDs and encoded in most supported formats. Music can be burned to CD / DVD format in compressed audio or CD format, possibly normalizing the volume level of songs in the process.

MediaMonkey supports music playback using MP3, AAC, OGG, WMA, FLAC, MPC, APE and WAV. It can adjust volume levels automatically using ReplayGain and MP3Gain.

The MediaMonkey Music Library attempts to organize and categorize a user’s music collection. During installation, it will scan the user’s hard drives for music files and add them to his library. Ranking and playback information can be imported from other media players such as Winamp and Windows Media Player. Podcasts are supported via Podcatcher, which allows the user to subscribe to podcasts that MediaMonkey will download automatically. It can also monitor the user’s hard drive to ensure that all changes are automatically updated in the library.

MediaMonkey can synchronize music files with most portable audio devices, including Apple iPod, Apple iPhone, Palm Pre and Android devices.

MediaMonkey supports third-party plugins to extend the core functionality. Plugins available include a scrobbler, a plugin for displaying lyrics, and a remote control web interface. MediaMonkey also supports the Winamp 2 API, allowing a user to use one of the many input, output, DSP and visualization plugins developed for Winamp.

MediaMonkey was 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 on June 7, 2002. Songs-DB 1.1 was the first release to provide Winamp plugin support. Version 1.2 was released on July 3, 2002 and included improved support for Winamp plugins, significant UI enhancements, 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 has been renamed to MediaMonkey. MediaMonkey 2.0 was released on August 25, 2003. MediaMonkey 2.2, released June 9, 2004, added device sync similar to iTunes. The latest major release of the 2.x series was MediaMonkey 2.5, released December 28, 2005. MediaMonkey 2.5 added enhanced sync for all iPods, Creative Labs and iRiver, as well as full support for FLAC. Minor versions of MediaMonkey continued for the following year, culminating in MediaMonkey 2.5.5 released on January 30, 2007.

MediaMonkey 3.0.1 was released on December 25, 2007. MediaMonkey 3 was designed specifically for large user libraries. This was seen in version 3.0.3, released June 19, 2008, which has increased the size of the library supported to over 100,000 tracks (from 50,000 tracks previously announced).

Media Monkey 4.0 was released on December 16, 2011. This release introduces better synchronization with Android devices, library sharing on DLNA / UPnP, improved audio output via WASAPI, the ability to operate from a key USB and CD extraction. MediaMonkey 4.1.0 was released on January 31, 2014. This release introduced wireless synchronization with MediaMonkey for Android and bidirectional sync, a darker appearance and UPnP enhancements. The current version is MediaMonkey 4.1.20, released in January 2018.

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