There's many different reasons that this could be occurring. In most cases this is because there aren't sufficient resources to perform all of the tasks that are running on your system. Why aren't there sufficient resources (when there were before)? Well, that's the hard part of figuring this problem out.
First, as a Windows installation becomes more mature (older and more customized), things are added to it. These things individually may not cause a noticeable problem, but added together they can significantly slow your system down. And this doesn't even consider if the "things" aren't cooperating - which will draw even more resources away from the the system.
To test for this, try playing the music from your hard drive without anything else attached. Also, terminate all running programs, and turn off as much stuff as you can in the System Tray (Notification Area next to the clock in the lower right corner of the screen)
If that works without stuttering, then start adding stuff - one thing at a time. Eventually you'll find that it starts stuttering. Then it's either the last thing that you added that's causing the stuttering, or it's the combination of all that you've added.
So, then try adding something else (a couple of running programs, for example) to see if adding anything will cause the stuttering. If that's the case, then it's just that the system has too much stuff running. If it doesn't, then you've found the problem in the paragraph above this one (the last thing that you added before the stuttering started).
If you look back about a month ago, you'll probably find some significant event that caused this problem to begin then. Something like an update, a new program, a new piece of hardware, etc.
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