Low Memory Error (Computer also reporting that my hard drive is almost filled)

Is there a diagnostic tool or something else I can do to find out why I'm getting an low memory error?
I have a Compaq Presario CQ60. I have 4.0GB of RAM and a 2.0 GHZ processor. 
I only have 5GB left on my hard drive. That can't be right!  The drive is 285 GB total. What told me that I had a problem was when I removed 40GB of music that I ripped from my CD collection. I moved it off. It cleared up room on my HD until i rebooted it a few times. Then all 40GB were mysteriously gone.  Program Files is 17.0 GB, MyDocuments 4.88GB, Music 5GB, Pictures 900MB, Videos 400 MB.  Downloads folder 1.14GB. When i run Defrag from Windows 7 Home Premium, it fails.
I can't believe I've run out of memory or hard drive space. I think something else is going on. I've been using this computer for years and what I'm doing now is no where near as intense as I've done in the past.
Is there a tool i can download and run? At one time, my computer did restart and do a check on the Hard Drive sectors but it returned no errors.  I don't know what to do.

Some very good tips here- includes tools to view what is using hdd space. (just be sure to ignore the ads)
http://www.howtogeek.com/125923/7-ways-to-free-up-hard-disk-space-on-windows/
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