Mac users may have it easy with iTunes, but Windows fans should look elsewhere for solid features, a customizable interface, and device syncing support that doesn't devour resources. That's why there's MediaMonkey, which juggles excellent library-management tools with skins, plug-ins, autotagging, links to the Amazon.com MP3 store, track encoding, podcast catching, and more.
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. 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. Throw $20 at the Monkey to get advanced features such as sleep, scripting, previewing, and on-the-fly file conversion when syncing with a portable device, but all the best features come in the free version.