[mapgrep]

Did you read the first (highest rated) answer? This has nothing to do with iTunes trying to be "an algorithmic DJ" rather than truly random, it has do with the confusing intersection of two features: You can pick the first song in the randomly "shuffled" playlist, and a shuffled playlist holds its order until it is re-shuffled.

The user posting the question assumed that when he double-clicked on the first song in the playlist, iTunes was re-shuffling the playlist. It wasn't. It assumed he wanted to start the playlist again. If he had picked any other song to double click after playback was stopped, it would have re-shuffled the playlist.

The solution was to toggle shuffle off and then on again. Then he'd force re-shuffling.

iTunes does have a separate algorithmic DJ feature, by the way, called iTunes DJ. No need to mess up shuffle. Shuffle is truly random.

[dpark]

> If he had picked any other song to double click after playback was stopped, it would have re-shuffled the playlist.

Pretty sure that's not the case, and the answer indicated otherwise. The order is stable until it's explicitly reshuffled.

[mapgrep]

I was mis-remembering how iTunes work there. It will auto-re-shuffle in some cases -- you don't always have to do it explicitly -- but it looks like it has more to do with whether you switch away from the playlist after the music stops playing. If I simply "pause" and select another song, without switching away, the order remains stable as you say. If I switch to say the Music library view, and then back, and double click a song (any song), it re-shuffles with that double-clicked song on top, playing.

[jvm]

That was part of the incorrect opinion parent was saying the user had.