Strange error/problem with itunes

iTunes loads normally, and I can add songs, etc. but when I press the play button, nothing happens. THe button depresses, then comes back up, but the music never starts playing and the time bar doesn't start to move like it does when a song is playing.
I know there's nothing wrong with the audio in my computer because I can play .mp3s just fine in Windows Media Player.
Sometimes, I have to reboot 3-4 times before iTunes will play the songs.
What could be going on?

Try turning off the Compatibility Mode:
iTunes for Windows: How to turn off Compatibility Mode
If that doesn't help, there are some additional suggestions in the document linked at the bottom of that page.
Hope this helps.

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