Is shuffle, in iTunes, actually random?

No. As the randomness is generated by a computer and computers find it very hard to generate truly random sequences.
iTunes can be set to select higher rated songs more often by checking the box “play higher rated songs more often” (obviously) on the party shuffle screen.

Steve Jobs addressed this a few years back. iTunes shuffle is geninely random, however people complained that songs were repeating, so in that particular iTunes update, he announced the ability to manipulate just how random “random” should be.

He said, despite favoring certain albums, artists or songs, the “random” system with iTunes is actually a very sophisticated program that numerically builds sequences differently according to each song, ironically this made it “less random.”

@Lightlyseared – in fact, it is impossible for a computer to generate truly random sequences. Officially, it’s pseudo-random.

Though I understand the question, as at my iPod Nano G2, it definitely looks like it isn’t really random. On the other hand, this might also be explained by some psychological effect, e.g. involving how long a song has been residing on your iPod, how much you like it, etc.

It started out pseudo-random, as random as a computer could make it. But this meant that people might hear two songs by the same artist back-to-back. This should happen occasionally if the arrangement is truly random, but people understood it as being less random because the computer was obviously grouping the songs.

So they made it less random in fact but more random in perception.

Ideas re: conspiracy theory.

And to @cwilbur’s observation re: perception vs. random as an input to interface design and interaction.