1-MediaMonkey (Windows)

MediaMonkey seems like an impossible combination of jukebox and library organizer. Sure, you can use it to just play your tunes, organize playlists, and sync with your mobile devices, but if your music library is a mess (like mine is), you can also use MediaMonkey to clean it up without a ton of effort. The layout and UI is customizable, and the player is snappy and fast even under the load of many-thousand song libraries, which is more than we can say for some of the other programs in the roundup. MediaMonkey does the basics too: It'll rip CDs, download podcasts, support file types like OGG and FLAC in addition to MP3, AAC, and others, and it'll automatically update your library based on changes to your library folders—so you can copy in new music without worrying MediaMonkey won't see it. If you like auto-generated playlists seeded by songs you own or like, MediaMonkey can do that too. It can convert file types on the fly if you need it to, stream media via DLNA to other devices on your network like a TV, receiver, or wireless stereo. Those of you who praised MediaMonkey specifically called out its customizability, customizable hotkeys, watch folders, and more. Even those of you who noted that you don't care for it as a music player love it as a music organizer, and turn to it to keep your files arranged, properly tagged, and easily searchable should you want to find something you downloaded a long time ago. Plus, MediaMonkey is free—although $25 gets you MediaMonkey Gold, which adds on some more features.