Ok, here goes, it is easier to compare this to the Tivo "Brain", anyone who has a Tivo knows that it can automatically record stuff that it thinks you would like, and sometimes it can get messed up - well I have a theory that iTunes has something similar, yet it is undocumented. I have 921 songs in my iTunes library, now this is not all that many songs compared to the number of songs some people here have, but it is still quite a few. Now, when I hit play in the main Library there is a 1 in 921 chance that it will pick a certain song to start on, and as I let it play through on random there is the same chance that it will play each song, yet it still seems to take a liking to certain albums, artists, songs and ratings. I have the song "Damn it feels good to be a gangster" nestled among other music, it is rated 1 star, iTunes picks it quite often. On my old computer (iMac g3 400) iTunes would ALWAYS play a CD of Irish music that I had ripped, it would pick songs from that album at least twice in a two hour period, whereas I can't remember it EVER picking a song by Our Lady Peace, of which I have one album and the same amount of songs. It seemed as if it wanted me to listen to the Irish Music. Now, you think that this could just be a fluke on my computer, not so, it also accurs on my new computer (iBook G4 1ghz), as well as my roommate at school's computer (BobInDaShadows at Macrumors). He has a collection of 58 songs that are 5 Star rated. At any given moment if one were to start playing this playlist it would play one of three songs to start off with; Jumper - Third Eye Blind; Abuse Me - Silverchair; and one other song of which I can't remember the name. In one test it played the three songs in succession as we fast forwarded through the playlist on random. On my new iBook I have already noticed that it seems to like Linkin Park (Especially the Reanimation album) and U2. I think that this could be something that was going to be developed but never made it, maybe a way that iTunes could sense your favorite songs, or maybe a way that it could reccommend stuff from the ITMS. It seems more than just a simple coincidence. Now that you are thinking about it go and play some music and pay attention, you'll notice it too.