Has anyone found that the random play within the library stinks?

I've come to realize that it ,more often than not, likes to play the same songs over and over, and in the same order... Occasionally, it may play a different song of a particular artist, but the artist are always in the same order... I've also noticed that ripping new CD's, doesn't seem to change things up much, nor do I ever hear my newer music...

 

Is there a way to reset the random play so that it plays all recently added music, as well as actually start playing them randomly?