Shuffle Playist Doesn't Work Correctly

I have a problem with my play lists on iTunes, I click "shuffle" and it "technically" does what it is suppose to do (It re arranges the order of the play list, but the only other re arrangement is the one that I put in there). I want it to be able to shuffle music like it was intended to do, so if someone can help that'd be great.

If you sort on the very first column above the numbers and click Shuffle, the songs will get shuffled and played in that order.
If you are sorting on any other column and click Shuffle, the songs will stay sorted by that column but they will play shuffled (the playlist jumps around when playing).

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