Windows Live Messenger will not show the song information you are listening to in iTunes because you either have Winamp or Windows Media Player running in the background. This can happen even if you haven’t touched or opened them. The program is running in the background, not doing anything, but it hijacks the song information being displayed by Messenger.
Follow these easy steps to solve the problem
1. Sign in and make sure you have the most recent version of windows live messenger.
2. Make sure the “show what I’m listening to” is checked
3. Now open iTunes and play music -> See if music is shown in messenger? If no proceed…
4. Follow these steps to close the windows media player service -> Press ctrl + alt + del
5. Choose “Start Task Manager” -> Go to the processes tab
6. Find wmplayer.exe *32 & WMPSideShowGadget.exe
7. Right click -> End Process
8. Check Windows Live Messenger to see if song information is being shown.
If it doesn’t work you may have another media player running a process i.e. spotify, winamp, vlc player.