Help I only have 50MB left!

I need some help PLEASE. I posted last week but have not resolved my issues and now only have 50MB left of storage.
I look all my files on an external drive so am unsure how I have used up all of my harddrive on my macbook air.
I have Mackeeper and here is a screenshot of my files.
I am just wondering if I delete my iTunes library would I have to upload all my music again?
Please please give me simple easy to follow instructions.

sberman is spot on. Avoid MacKeeper and any other third party Mac cleaning utillities. They can do far more harm than good.
Your Mac runs maintenance in the background for you > Mac OS X: About background maintenance tasks
Explains, "Other" in storage >   OSX Tips The Storage Display
Freeing space on your Mac OS X startup disk

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