Playing Windows Media on an iPod
Michael asks, Can you play a Windows Media file on an iPod or download to iTunes?
Unfortunately you can't play a Windows Media file on your iPod. Apple doesn't support playback of WMA or WMV files on the iPod, in part because it might hurt their business model in selling you something they hope you'll fill with music and video from their store. The good news is, you can convert Windows Media files to an iPod supported format and play them back either in iTunes or on your iPod after the conversion completes. The caveat to this is Windows Media files purchased from places like MTV URGE, Napster, Yahoo or any of the other online stores using Windows Media with DRM will not work and cannot be converted. Depending on whether the file you want to play is audio or video and how many files you want to convert, there are a number of ways to approach this problem.
iTunes for Windows will convert every WMA file on your hard drive to either AAC or MP3 given enough time. Simply import the file or folder of files you want to convert from File > Import or File > Add Folder to Library. The software then converts the files based on your import preferences.
If you need to convert video files for playback in iTunes or on your iPod, there are almost too many choices. One easy option is Videora iPod Converter, which converts most video formats to something an iPod can play. The options are a bit confusing and you may need to try several before you find one that both looks good and doesn't take up too much space on your iPod.
I really like the interface Pinnacle created for their Mobile Media Converter software. It's drag-and-drop simple; it converts files for both PSP and iPod playback; most importantly, you don't need to worry about whether or not your software will convert the files because they've got everything you need bundled with the app. It costs $30, but avoiding frustrations when things don't work is easily worth that.
If you want to convert WMV videos on a Mac, the best option is spending $29 for the upgrade from Flip4Mac WMV Player. There are free solutions, but the time you waste implementing them is worth the price even if you valued your time at something less than minimum wage.