iTunes plays the same song over and over again.

I have created several playlists on my Itunes for Windows. I want the songs to play at Random...but it plays the same song over and over again. If I hit the random button, it will play a different song, but it will then play that song over and over and over again. So, if I want to go to the next song, there is always a requirement that I manually set it to the next song.

It's odd because I have been using Itunes while listening to music on my computer and this never happened before.

Any thoughts?

- Jack