Why does iTunes play the whole album on shuffle?
It does this because of some broken code in the most recent releases of iTunes. They added a new feature to help those of us who want to properly group, and play in order, classical music. If the Work tag is populated then once itunes sees something in that tag it plays all of the items on the album with the same Work tag. Many have used the groupings field in the past and the latest version grabs the groupings info and stuffs it into the new Work field. So if perhaps you had something like SONY (an album label) in the groupings filed now iTunes thinks every track on the album is part of a classical Work called Sony and that you will want to hear the album in order as you would if it were movements of a classical work. Very frustrating and foolish error on their part. One hopes the can fix this in the next release as it makes shuffle play pretty much un-usable if one uses the grouping field as it was originally intended - to group songs in some way like as Jazz.Standards or World.Music, etc.