Syncing an iPhone with iTunes is about as seamless as it gets, while Android users are often left with a much clunkier experience—or at least having to figure out what desktop music player best fits their syncing needs. Here's how our favorite music players stack up against one another in Android-syncing prowess.
We know the choice of desktop music player is an extremely personal one, and you have so many great players to choose from. However, if you have an Android phone, you not only have to worry about features on the desktop, but also how well it syncs to your device—and sometimes that's a bit harder to see. Every player works a bit differently, so we've tested them all and put together a handy chart to help you see which players are the most Android friendly, along with a breakdown of how each one performs.
iTunes (via iSyncr)
iTunes obviously doesn't sync with Android out of the box, but if you have to manage your music library in iTunes (say, if you also have an iPod), previously mentioned iSyncr will get the job done. iSyncr is an Android app slash portable Windows/Mac app that you install on your device, and when you want to sync, you just plug it in and run the EXE (or Mac app) on your phone's SD card. From there, you can choose what playlists to sync, including videos, and it'll even sync play counts for you. With the addition of the iSyncr Wi-Fi addon, you can even sync your device without ever plugging it in. If you edit your playlists on your device, it'll edit them on your phone, and delete any tracks you no longer wish to sync. Short of transcoding and support for podcasts, it's one of the best syncers out there. The fact that it's packaged as a portable app is very nice too.
Note: Many of you are mentioning DoubleTwist in the comments, and no, we didn't forget it. DoubleTwist was fine when there was no other syncing solution, but since iSyncr has come out, we've seen no reason to use DoubleTwist. It's a whole extra media player you have to install, while iSyncr is a bloat-free, portable app that sits on your device and does nearly everything you could possibly want—including Wi-Fi sync. If you haven't checked it out and you're still using DoubleTwist, we recommend giving it a try. It's much better. That said, DoubleTwist should do everything iSyncr does—including Wi-Fi sync—so if you don't like iSyncr, it'll also work for syncing all your iTunes tracks and playlists.
Winamp
Winamp is easily the best player on Windows for syncing to your Android phone. There's very little it doesn't do. When you first plug in your device, Winamp will recognize it and show it under the "Devices" tab in the left sidebar. From there you can configure which playlists sync to your device and/or specify an advanced search query to decide which songs get synced (e.g. "genre does not equal Holiday"). You can set it to automatically sync as soon as you plug it in, choose which podcasts are synced to your device, automatically fill empty space with higher rated songs, and transcode higher-bitrate and incompatible tracks on-the-fly, so everything works correctly on your phone (though it sadly won't transcode videos).
You can even tell it what folders to sync your media to, and if you remove a track from your sync list, it will ask you if you want to delete them or leave them—which is awesome to be given the choice. It'll even sync over Wi-Fi, if you have Winamp for Android installed on your device (though you don't need to use it as your player for this to work—you just need it to communicate with your computer). In short, Winamp syncs with Android as well as iTunes syncs with iOS devices—if not better.
MediaMonkey
MediaMonkey syncs with Android almost as well as Winamp, with a few caveats. When you plug in your device, you'll see an iTunes-like pane that pops up and asks you what you want to sync. You can select playlists, music, and podcasts from there, and set your device to sync every time you plug it in. You can also fill any unused space with high rated songs from your library. It'll also delete files you remove from your sync list, and sync files from the device back to your PC. It doesn't sync over Wi-Fi, however, and you have to purchase MedaMonkey Gold to transcode songs on-the-fly.
MusicBee
MusicBee is a lesser-known, but fantastic music player for Windows that syncs surprisingly well with Android. You can tell it where to sync music, choose what playlists are synced, choose how to copy artwork, convert tracks on-the-fly, and set it to sync as soon as you plug in the device. It also has podcast support, though it only lets you sync all episodes or all unplayed episodes—nothing in between. Unlike all the other players, though, MusicBee won't sync videos, because it doesn't support having videos in its library. It also has no option for Wi-Fi sync. Overall, though, it's a great balance between solid media management on the desktop and great Android support, if you aren't a fan of Winamp.
Windows Media Player
Windows Media Player may not be the worst program in the world, but its Android syncing leaves a lot to be desired. The only advantage it has over just dragging your music folders to your phone in Windows Explorer is that you can selectively sync playlists—but it won't sync the actual playlists themselves, just the songs on it. It also won't delete any tracks you remove from the device, doesn't support podcasts, won't transcode, or sync over Wi-Fi. All it really is is a method to copy songs from your library to your device, it doesn't truly "sync" anything. If you want any kind of real syncing, we recommend staying away from Windows Media Player.
Foobar2000
We didn't want to neglect Foobar2000, but sadly, Foobar2000 neglected us. Being the minimalist player that it is, there's little to no support for syncing devices, short of an Android plugin that we couldn't even get to install. So, we've left it out of the chart above, but if you know of a reliable way to sync Foobar2000 with your device, please let us know.
The Alternative: Streaming Music
There is, of course, another option entirely, and that's using a service like Spotify or Google Music to just stream music to your device. Each of these services has their own advantages and disadvantages (Google Music, for example, can only sync playlists from iTunes or Windows Media Player), but they're so different than desktop syncing that we didn't include them here. However, if syncing your music over USB has given you a headache, be sure to check out our cloud music comparison to see which streaming service might suit you best.
There you have it. These obviously aren't the only music players on Windows, but they are our top five favorites, and between them you should be able to find one that suits you in both desktop and Android-syncing features. Winamp is still our favorite, due to its extremely powerful Android syncing, though MediaMonkey is a close second, with MusicBee and iSyncr being good second choices.