Seriously, I love iTunes as a great music organizing, burning and playing tool, but when it comes to iTunes DJ (or iPod shuffle feature for that matter) it just drives me nuts. There is no real randomness to the selection of songs. I have 45GB worth of music in my itunes library and yet iTunes DJ will always go for a select few albums/compilations most of the time, and throw in a handful of other stuff to make it seem random. Namely, I have this 6-CD oldies collection and it gets played the most. Each time I fire iTunes DJ up it will go for this collection. Here's a screenshot I just took of it: Notice out of the 15 upcoming songs, 5 are off this oldies compilation. Now how is this random? Oh yeah, and my single Steppenwolf greatest hits album is another one of his favorites- iTunes DJ will play a Steppenwolf song each time I run it, oftentimes more than one song off this album. What the hell is the matter with that? I am now really thinking about abandoning iTunes for a real "random-selection" player, such as Foobar, although I guess I will miss the other great features of iTunes. Anyone else in the same boat?