IMac :: Cannot Restart Properly - Screen Just Keep Spinning

I only restart about once a week or so and for about the last four to six weeks, I've been having issues restarting my 27" iMac, which is about five months old. What happens is that after I click restart and it logs out, it gets to the blue screen and the status bar in the center of the screen just keeps spinning and spinning (not the beach ball, the other one). I've let it run for 30 minutes before and it never shuts down so I have to hold down the power button and then push it again to start it up.

Problem is, I'm starting to feel the effects of that shortcut now with iTunes randomly pausing more and more times and for longer and longer amounts of time when playing a video. I'm guessing it has something to do with the processes that are normally run during a regular restart not being run since it won't perform a natural restart.