My iPod is getting a little old (in digital terms — if it were a hammer, it would still be in its early years of usefulness), and the battery has lost a lot of its capacity, but I didn’t expect this:
Every now and then, the “shuffle” function will forget that it’s supposed to be shuffling by song, and will continue playing a particular performer’s songs until it runs out. You can fast-forward it through the supposedly-shuffled playlist, but if it falls into this while playing songs by a favorite performer, or an especially prolific act (such as the Magnetic Fields), it can take a great many button-pushes to get the shuffle function out of its rut.
Yes, I have checked, and the “shuffle” function is checked for “by song,” not by artist or album. Moreover, it doesn’t always get tracked for an artist even when I have multiple selections by that artist.
Worse things happen at sea, of course, but it’s an odd little nuisance of a bug.
Have you tried doing the “reset your iPod” thing from within iTunes? My first suspicion would be some sort of odd corruption in the firmware.