As I know, iPod can't work with windows media player. You can only use iTunes to put music on iPod.
For more tips about iPod, you may refer to this iPod FAQ.
http://www.mac-dvd.com/ipod-tips-and-ipod-faq.html
Hope it helps. Contact me if you have any other question.
Windows Media Player had Mac version ever. But Microsoft stop offering technical support to Apple and as a result it isn't available now. But you can look for solution on how to play WMA on Mac in this article. It works.
https://www.leawo.org/tutorial/how-to-play-wma-on-mac-1410.html?fixya=1410
For Windows OS, iPod supports no WMA/WMV files from Windows Media Player due to two reasons:
1. Unsupported file format;
2. Protected WMA/WMV files.
So you need to remove the protection and convert WMA/WMV to proper files format like M4A/M4V, Daniusoft Media Converter Pro is recommended.
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