A friend was experiencing a really annoying problem with her iPhone. She would hit shuffle within a playlist or album. Instead of shuffling the songs on that list, it would repeat the first song over and over.
Took me a while to figure it out, but I found the problem and how to fix it.
While there are several web discussions about iPhone shuffle problems, I had trouble finding the answer but eventually did figure it out. This post should make it more obvious.
First, you need to tap the screen while you're playing a song. You should see something like this:
Here's a closer look: