Chris Anderson makes the case against the iPod Shuffle:

So that, in a nutshell, is the case against the Shuffle. For anyone with a big music collection (thousands of tracks) a random walk through their entire library is statistically likely to be an unwelcome reacquaintance with mistaken purchases, whim rips, filler album tracks and embarrassing ghosts of music taste past. And if you’re anything like me, that gets annoying real fast.

The only way the Shuffle would make sense to me is if it were scaping songs from a collection that I kept well vetted.