MediaMonkey

MediaMonkey is a Windows-based digital media player and library manager designed to help users organize and play large collections of music and video files. The program provides robust tagging and metadata management, automatic album art retrieval, file organization, and advanced search capabilities to help locate files quickly. It supports a wide range of audio formats (such as MP3, AAC, FLAC, OGG, WMA, M4A) and video formats, and can edit or repair metadata across formats, with batch tagging features and customizable tagging rules.

The software includes features for library management, dynamic and smart playlists, and automation tools such as Auto-DJ for automatic playlist generation. It can rip audio CDs, convert between formats, and rename files based on user-defined templates. MediaMonkey offers synchronization with portable devices and has companion apps for Android; a server component enables streaming to UPnP/DLNA devices on a local network.

The base version is free, with a paid Gold edition that adds features such as enhanced tagging options, more advanced device synchronization, auto-tagging from online databases, and additional customization options. The application is known for handling very large libraries, and it provides a familiar interface for users migrating from other media players.