Converting playlists with drag & drop...
Try this to convert playlists from Windows Media Player (WMP) to iTunes:
1. Save your WMP playlists as M3U files.
To do this you can use the "Save Playlist As" option from the list pane when you're editing the playlist. Then change the "Save as type:" field from WPL (the default) to M3U and also specify the name and location of the file.
This may also work with WPL files but I have not tried it. I use M3U files for interoperability with the media adapter I use on my stereo system.
2. Open Windows Explorer to the directory where you saved the M3U file.
3. Open iTunes alongside Windows Explorer.
4. Drag the M3U file from Windows Explorer to the PLAYLISTS section of iTunes. (If you want to create it as a new playlist be sure to drop it in the left-hand pane under the PLAYLISTS section.)
This process will then read the M3U file and create the playlist in iTunes.
If you're a multi-player household as we it may be helpful to know you can also convert iTunes playlists to WMP with a slightly different drag & drop approach (you do it by song rather than by playlist):
1. Open both iTunes and WMP.
2. In WMP make sure you have an empty list pane shown to receive the playlist. In WMP 11 the list pane can be hidden and you can show the list pane by clicking the left arrow up next to the search box.
3. In iTunes click on the playlist you want to convert to WMP to bring it up the full song list.
4. Highlight all the songs you want to convert to the WMP playlist. (Basically just click on the first song and then shift+click on the last song to select them all.)
5. Then drag all the songs from iTunes to the list pane in WMP.
6. Then save the playlist in WMP.