UPDATE (12/18/06):  By popular demand, I've added an article on how to convert your (unprotected) AAC files in iTunes to MP3s that can be played on any MP3 player or program. 

 

UPDATE (11/27/06):  This blog entry is about how to get your iTunes library and metadata in sync with Windows Media Player.  This article will not help you move songs you bought on the iTunes Music Store over to Windows Media Player.  This is because of a layer of copy-protection Apple puts on their files called "FairPlay", which they have not licensed for use on a computer outside of their own iTunes software.  I've also been playing with Microsoft's new Zune device, which appears to automatically move your iTunes library over (sans iTunes Music Store purchases.)

 

In preparation for my big media player move from my iPod Photo to a new Toshiba Gigabeat S Portable Media Center, it was time for me to say goodbye to iTunes and hello to Windows Media Player 11.  Moving a music library between media players can be a painful process, so I thought I’d share how I was able to migrate my library, including my song ratings, to the new player using one awesome app:  MusicBridge.

 

First of all, it’s important to know that I suggest completely backing up your iTunes library folder before starting any of this, just in case.  By default, your iTunes library should be at c:\<Your Documents Folder>\My Music\iTunes.  (For example, mine is at c:\Documents and Settings\Joe\My Documents\My Music\iTunes.)

 

Basically, after starting up the Music Bridge application, you’re asked which way you’d like to sync your libraries:  WMPàiTunes, iTunesàWMP, or a two-way sync.  If you haven’t added any music to your WMP library, select the iTunes to WMP sync option.  You are able to select exactly *what* you want to sync—be it just the songs, your playlists, your ratings, etc.  I chose to sync everything, and everything it synced.  I was totally pumped when I opened WMP 11, waited for a couple of minutes while it was updating its library, and then noticed that all my music *and* ratings were preserved.  For some reason, my Smart Playlists did not transfer over, so I recreated them as auto-playlists.  I unfortunately lost my play counts.

 

One painful limitation, especially given WMP 11’s love of using album art in the interface, is that WMP and iTunes handle album art completely differently—so you’ll album art isn’t going to show up for all of your music.  If you set WMP to “Update Music Files by Retrieving Media Info from the Internet” (ToolsàOptionsàPrivacy), WMP will update your album art automatically in the background using a web service (as long as WMP is open).  To trigger this update automatically, you’ll want to select “ToolsàApply Media Information Changes”, which will bring this process to the foreground (and not allow you to do anything else with WMP until it is done.)

 

From my experience, this will get you about 2/3 of your albums’ art.  For that remaining third, you either:

 

1.)    Have incorrect metadata about your music, such as artist and album, or

2.)    You have an album that doesn’t have art in the database (not super common, but common enough)

 

You’ll need to manually go through your files, one by one, and fix the metadata and album art.  To do this, the best way is to right-click on the song from WMP in question and select “Find Album Info” from the contextual menu.  A window will pop up and it will search for your song.  If it doesn’t find it, you’ll be able to broaden the scope of your search, and hopefully eventually find some album info for it, including the album art.

 

This stuff isn’t perfect in WMP 11—there are a few bugs in the beta version around applying the newly found album information to a song—but it’s a start.  There’s another program to help fix your metadata (not including album art) that’s media player-agnostic called “Music Brainz” that actually uses a frequency analysis of your song to find appropriate metadata.  Check it out, but be warned that I’ve found that it’s about 90% accurate—I’ve had it re-label some songs completely incorrectly—but it’s unique and constantly improving, and probably worth a shot if you’re trying to fix up your library.