The work around is the following…
Open up Windows Media Player, and go to Tools => Options (You might need to hit the ALT key to see the hidden menu)
Click the Plug-ins tab, then on the Category Column, Click on Background and make sure Windows Live Messenger Music Plug-in is ticked. If not, tick it and Apply then OK.
See the following screenshot for more info…

Now you should be able to Show what you play on Windows Media Player.
Source: http://www.nishv.com/2007/10/live-messenger-show-what-im-listening-to-doesnt-work/
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