Despite a glut of free player/encoders, it's tough to find one that meets our expectations. Formerly known as Sound DB, MediaMonkey has excellent library-management tools that keep the largest digital music collections well organized. Stir that up with integrated CD and DVD burning, a stellar interface, a full-featured encoder, and the ability to sync with portable audio devices such as the iPod, and you have a pretty compelling product.
Upon first launch, the program scans your drive for supported digital media files to add to the library. Files are sorted based on their ID3 tags, and the helpful Auto-Rename and Auto-Tag From Filename features keep untagged tracks from falling through the cracks. Party mode locks down your library while still allowing people to request songs. Auto DJ plays selections from your library even when there are no requests in the queue, and the all-important iPod and portable device synchronization works well. Third-party plug-ins are available from the site if you want to tinker with the playback and encoding engine or add additional sound-processing effects. The interface is well designed, with clean, colorful icons throughout.
Considering the overall polish of this application, you'll be hard-pressed to find anything you don't like. Although it's definitely geared toward managing extensive collections, just about anyone will appreciate the comprehensive feature set. For $20, MediaMonkey Gold adds advanced features such as sleep, scripting, previewing, and on-the-fly file conversion when syncing with a portable device.