This has been bugging me for ages. My preferred way to listen to my music collection is on Shuffle mode on my iPod Touch. I do this by choosing Music|Albums|All Songs|Shuffle. Within my Music Collection are lots of songs that I have more than one version off, live versions, soundtrack versions, compilation versions etc, and its been driving me crazy that Shuffle was playing each version in sequence. Why would I want to listen to the same song twice? That ain’t random!
I guess I’m slow, but I finally understood why this is happening today. This Shuffle menu option is not choosing songs randomly, instead it progresses through my collection in alphabetical order, just starting at a random point in the collection.
To truly shuffle the play order you need to tap the album artwork and then tap the shuffle icon that appears on the right hand side. Maybe this icon got switched off at some point, but I don’t recall doing that, I had to go hunting in the manual today to find out it even existed.
IMHO its a bug that choosing Music|Albums|All Songs|Shuffle doesn’t force this shuffle icon on.