Preface: one of Apple's selling points for the new v5 iTunes is a more "intelligent" shuffle algorithm.
Story: I'm sitting here innocently listening to some tunes in Party Shuffle mode and I hear this segue.
That's Moby's "Guitar, Flute, and String" into Chris Rice's arrangement of "For the Beauty of the Earth". Yes, they two aren't in the same key, but that's about as good as it gets for a semi-random machine-generated segue, huh?
Just thought I'd share.