So one of the problem with random playlists is that they don’t deal well with continuous mix music. Things like the Global Underground collections are great CDs, but only when played as a whole. Isolate a track, and while it may be fine on it’s own, it loses much of its meaning and significance when removed from the continuous mix. It can in fact be quite jarring to come across some of this stuff, coming in mid-beat, or somesuch, or ending just as a transition begins.
Of course, sometimes you get some wonderfully sublime transitions, such as just happened, where the Bill Hicks bit about Waco segues flawlessly into Django Reinhardt & Stephen Grappelli’s ‘undecided’. I mean, you couldn’t have that work better if you tried.