Leonard Mlodinow touches on this issue in
The Drunkard's Walk[1]. If I remember correctly, his explanation was something along the lines of this: a truly random playlist is not desirable to most users, which challenges the claim "I do believe the ordering is truly random the first time it's generated" in the top answer. Mlodinow explains that most people really
don't understand randomness, and a "truly random" playlist might have the same song twice in a row, play a few songs from the same album in the normal order, and things like that. Some people don't realize that rolling 1,2,3,4,5,6 on a die in order is as likely as 6,4,1,2,5,3 even though the second set of outcomes might seem more likely because it looks more random. To outcount for this, iTunes actually does use an algorithm to make the shuffled playlist "better" than a truly random one.
Of course, by some definitions, even rand() isn't random enough, so I can see why people argue about it. The book doesn't even provide a rigorous definition of the concept, but it was never intended to be a serious treatise on statistics.
1. http://www.nytimes.com/2008/06/08/books/review/Johnson-G-t.h...