When you press Play while in the main menu, it should start 'Shuffle Songs' instead of playing from the top of the alphabet, so that !!! and ...And You Will Know Us By The Trail Of Dead don't have such an unfair advantage (also, I'm getting sick of a few of the low-alphabetical artists, though I'll never get sick of 400 Blows). Ignore this - I hadn't noticed that the 'Now Playing' item disappears when there's nothing playing, which leaves 'Shuffle Songs' easily accessible at the end of the list.
This would make more sense then, too.